id	sid	tid	token	lemma	pos
eurjchem-788	1	1	untitled	untitle	VERB
eurjchem-788	1	2	european	european	PROPN
eurjchem-788	1	3	journal	journal	PROPN
eurjchem-788	1	4	of	of	ADP
eurjchem-788	1	5	chemistry	chemistry	NOUN
eurjchem-788	1	6	4	4	NUM
eurjchem-788	1	7	(	(	PUNCT
eurjchem-788	1	8	3	3	NUM
eurjchem-788	1	9	)	)	PUNCT
eurjchem-788	1	10	(	(	PUNCT
eurjchem-788	1	11	2013	2013	NUM
eurjchem-788	1	12	)	)	PUNCT
eurjchem-788	1	13	216‐219	216‐219	PROPN
eurjchem-788	1	14	european	european	ADJ
eurjchem-788	1	15	journal	journal	PROPN
eurjchem-788	1	16	of	of	ADP
eurjchem-788	1	17	chemistry	chemistry	NOUN
eurjchem-788	1	18	issn	issn	PROPN
eurjchem-788	1	19	2153‐2249	2153‐2249	PROPN
eurjchem-788	1	20	(	(	PUNCT
eurjchem-788	1	21	print	print	NOUN
eurjchem-788	1	22	)	)	PUNCT
eurjchem-788	1	23	/	/	SYM
eurjchem-788	1	24	issn	issn	PROPN
eurjchem-788	1	25	2153‐2257	2153‐2257	NUM
eurjchem-788	1	26	(	(	PUNCT
eurjchem-788	1	27	online	online	ADJ
eurjchem-788	1	28	)	)	PUNCT
eurjchem-788	1	29			NOUN
eurjchem-788	2	1	2013	2013	NUM
eurjchem-788	3	1	eurjchem	eurjchem	PROPN
eurjchem-788	3	2	doi:10.5155	doi:10.5155	ADJ
eurjchem-788	3	3	/	/	SYM
eurjchem-788	3	4	eurjchem.4.3.216‐219.788	eurjchem.4.3.216‐219.788	ADJ
eurjchem-788	3	5	european	european	ADJ
eurjchem-788	3	6	journal	journal	PROPN
eurjchem-788	3	7	of	of	ADP
eurjchem-788	3	8	chemistry	chemistry	PROPN
eurjchem-788	3	9	journal	journal	PROPN
eurjchem-788	3	10	homepage	homepage	NOUN
eurjchem-788	3	11	:	:	PUNCT
eurjchem-788	3	12	www.eurjchem.com	www.eurjchem.com	X
eurjchem-788	3	13	activated	activate	VERB
eurjchem-788	3	14	bentonite	bentonite	NOUN
eurjchem-788	3	15	promoted	promote	VERB
eurjchem-788	3	16	friedländer	friedländer	NOUN
eurjchem-788	3	17	condensation	condensation	NOUN
eurjchem-788	3	18	reactions	reaction	NOUN
eurjchem-788	3	19	:	:	PUNCT
eurjchem-788	3	20	synthesis	synthesis	NOUN
eurjchem-788	3	21	of	of	ADP
eurjchem-788	3	22	thieno[2,3‐b]quinolinones	thieno[2,3‐b]quinolinone	NOUN
eurjchem-788	3	23	and	and	CCONJ
eurjchem-788	3	24	tacrines	tacrine	NOUN
eurjchem-788	3	25	analogues	analogues	PROPN
eurjchem-788	3	26	derivatives	derivative	NOUN
eurjchem-788	3	27	khaireddine	khaireddine	NOUN
eurjchem-788	3	28	mohamed	mohame	VERB
eurjchem-788	3	29	dridi	dridi	PROPN
eurjchem-788	3	30	a	a	DET
eurjchem-788	3	31	,	,	PUNCT
eurjchem-788	3	32	b	b	NOUN
eurjchem-788	3	33	,	,	PUNCT
eurjchem-788	3	34	*	*	ADJ
eurjchem-788	3	35	,	,	PUNCT
eurjchem-788	3	36	ridha	ridha	NOUN
eurjchem-788	3	37	ben	ben	PROPN
eurjchem-788	3	38	said	say	VERB
eurjchem-788	3	39	a	a	DET
eurjchem-788	3	40	,	,	PUNCT
eurjchem-788	3	41	c	c	X
eurjchem-788	3	42	,	,	PUNCT
eurjchem-788	3	43	youssef	youssef	PROPN
eurjchem-788	3	44	arfaoui	arfaoui	PROPN
eurjchem-788	3	45	a	a	PRON
eurjchem-788	3	46	,	,	PUNCT
eurjchem-788	3	47	c	c	PROPN
eurjchem-788	3	48	and	and	CCONJ
eurjchem-788	3	49	abdullah	abdullah	PROPN
eurjchem-788	3	50	sulaiman	sulaiman	PROPN
eurjchem-788	3	51	al‐ayed	al‐aye	VERB
eurjchem-788	3	52	a	a	DET
eurjchem-788	3	53	a	a	DET
eurjchem-788	3	54	department	department	NOUN
eurjchem-788	3	55	of	of	ADP
eurjchem-788	3	56	chemistry	chemistry	NOUN
eurjchem-788	3	57	,	,	PUNCT
eurjchem-788	3	58	college	college	NOUN
eurjchem-788	3	59	of	of	ADP
eurjchem-788	3	60	sciences	science	NOUN
eurjchem-788	3	61	and	and	CCONJ
eurjchem-788	3	62	arts	art	NOUN
eurjchem-788	3	63	,	,	PUNCT
eurjchem-788	3	64	qassim	qassim	PROPN
eurjchem-788	3	65	university	university	NOUN
eurjchem-788	3	66	,	,	PUNCT
eurjchem-788	3	67	al‐rass	al‐rass	PROPN
eurjchem-788	3	68	,	,	PUNCT
eurjchem-788	3	69	53	53	NUM
eurjchem-788	3	70	,	,	PUNCT
eurjchem-788	3	71	kingdom	kingdom	NOUN
eurjchem-788	3	72	of	of	ADP
eurjchem-788	3	73	saudi	saudi	PROPN
eurjchem-788	3	74	arabia	arabia	PROPN
eurjchem-788	3	75	b	b	PROPN
eurjchem-788	3	76	laboratory	laboratory	NOUN
eurjchem-788	3	77	of	of	ADP
eurjchem-788	3	78	organic	organic	ADJ
eurjchem-788	3	79	chemistry	chemistry	NOUN
eurjchem-788	3	80	,	,	PUNCT
eurjchem-788	3	81	department	department	NOUN
eurjchem-788	3	82	of	of	ADP
eurjchem-788	3	83	chemistry	chemistry	NOUN
eurjchem-788	3	84	,	,	PUNCT
eurjchem-788	3	85	faculty	faculty	NOUN
eurjchem-788	3	86	of	of	ADP
eurjchem-788	3	87	sciences	science	NOUN
eurjchem-788	3	88	,	,	PUNCT
eurjchem-788	3	89	el	el	PROPN
eurjchem-788	3	90	manar	manar	PROPN
eurjchem-788	3	91	university	university	PROPN
eurjchem-788	3	92	,	,	PUNCT
eurjchem-788	3	93	el	el	PROPN
eurjchem-788	3	94	manar	manar	PROPN
eurjchem-788	3	95	ii	ii	PROPN
eurjchem-788	3	96	,	,	PUNCT
eurjchem-788	3	97	tunis	tunis	VERB
eurjchem-788	3	98	1060	1060	NUM
eurjchem-788	3	99	,	,	PUNCT
eurjchem-788	3	100	tunisia	tunisia	PROPN
eurjchem-788	3	101	c	c	PROPN
eurjchem-788	3	102	unité	unité	PROPN
eurjchem-788	3	103	physico‐chimie	physico‐chimie	PROPN
eurjchem-788	3	104	des	des	PROPN
eurjchem-788	3	105	matériaux	matériaux	PROPN
eurjchem-788	3	106	condensés	condensés	PROPN
eurjchem-788	3	107	,	,	PUNCT
eurjchem-788	3	108	département	département	X
eurjchem-788	3	109	de	de	X
eurjchem-788	3	110	chimie	chimie	PROPN
eurjchem-788	3	111	,	,	PUNCT
eurjchem-788	3	112	faculté	faculté	PROPN
eurjchem-788	3	113	des	des	PROPN
eurjchem-788	3	114	sciences	sciences	PROPN
eurjchem-788	3	115	,	,	PUNCT
eurjchem-788	3	116	université	université	PROPN
eurjchem-788	3	117	tunis	tunis	PROPN
eurjchem-788	3	118	el	el	PROPN
eurjchem-788	3	119	manar	manar	PROPN
eurjchem-788	3	120	,	,	PUNCT
eurjchem-788	3	121	el	el	PROPN
eurjchem-788	3	122	manar	manar	PROPN
eurjchem-788	3	123	ii	ii	PROPN
eurjchem-788	3	124	,	,	PUNCT
eurjchem-788	3	125	tunis	tunis	VERB
eurjchem-788	3	126	1060	1060	NUM
eurjchem-788	3	127	,	,	PUNCT
eurjchem-788	3	128	tunisia	tunisia	NOUN
eurjchem-788	3	129	*	*	PUNCT
eurjchem-788	3	130	corresponding	correspond	VERB
eurjchem-788	3	131	author	author	NOUN
eurjchem-788	3	132	at	at	ADP
eurjchem-788	3	133	:	:	PUNCT
eurjchem-788	3	134	department	department	NOUN
eurjchem-788	3	135	of	of	ADP
eurjchem-788	3	136	chemistry	chemistry	NOUN
eurjchem-788	3	137	,	,	PUNCT
eurjchem-788	3	138	college	college	NOUN
eurjchem-788	3	139	of	of	ADP
eurjchem-788	3	140	sciences	science	NOUN
eurjchem-788	3	141	and	and	CCONJ
eurjchem-788	3	142	arts	art	NOUN
eurjchem-788	3	143	,	,	PUNCT
eurjchem-788	3	144	qassim	qassim	PROPN
eurjchem-788	3	145	university	university	NOUN
eurjchem-788	3	146	,	,	PUNCT
eurjchem-788	3	147	al‐rass	al‐rass	PROPN
eurjchem-788	3	148	,	,	PUNCT
eurjchem-788	3	149	53	53	NUM
eurjchem-788	3	150	,	,	PUNCT
eurjchem-788	3	151	kingdom	kingdom	NOUN
eurjchem-788	3	152	of	of	ADP
eurjchem-788	3	153	saudi	saudi	PROPN
eurjchem-788	3	154	arabia	arabia	PROPN
eurjchem-788	3	155	.	.	PUNCT
eurjchem-788	4	1	tel	tel	PROPN
eurjchem-788	4	2	.	.	PUNCT
eurjchem-788	4	3	:	:	PUNCT
eurjchem-788	5	1	+966.05.59928442	+966.05.59928442	ADJ
eurjchem-788	5	2	;	;	PUNCT
eurjchem-788	5	3	fax	fax	NOUN
eurjchem-788	5	4	:	:	PUNCT
eurjchem-788	5	5	+966.06.3335160	+966.06.3335160	ADJ
eurjchem-788	5	6	.	.	PUNCT
eurjchem-788	5	7	e‐mail	e‐mail	PUNCT
eurjchem-788	6	1	address	address	NOUN
eurjchem-788	6	2	:	:	PUNCT
eurjchem-788	6	3	khairydridi@yahoo.fr	khairydridi@yahoo.fr	PROPN
eurjchem-788	6	4	(	(	PUNCT
eurjchem-788	6	5	k.m	k.m	PROPN
eurjchem-788	6	6	.	.	PROPN
eurjchem-788	6	7	dridi	dridi	PROPN
eurjchem-788	6	8	)	)	PUNCT
eurjchem-788	6	9	.	.	PUNCT
eurjchem-788	7	1	article	article	NOUN
eurjchem-788	7	2	information	information	PROPN
eurjchem-788	7	3	abstract	abstract	ADV
eurjchem-788	7	4	received	receive	VERB
eurjchem-788	7	5	:	:	PUNCT
eurjchem-788	7	6	01	01	NUM
eurjchem-788	7	7	april	april	PROPN
eurjchem-788	7	8	2013	2013	NUM
eurjchem-788	7	9	received	receive	VERB
eurjchem-788	7	10	in	in	ADP
eurjchem-788	7	11	revised	revise	VERB
eurjchem-788	7	12	form	form	NOUN
eurjchem-788	7	13	:	:	PUNCT
eurjchem-788	7	14	25	25	NUM
eurjchem-788	7	15	april	april	PROPN
eurjchem-788	7	16	2013	2013	NUM
eurjchem-788	7	17	accepted	accept	VERB
eurjchem-788	7	18	:	:	PUNCT
eurjchem-788	7	19	08	08	NUM
eurjchem-788	7	20	may	may	PROPN
eurjchem-788	7	21	2013	2013	NUM
eurjchem-788	7	22	online	online	NOUN
eurjchem-788	7	23	:	:	PUNCT
eurjchem-788	7	24	30	30	NUM
eurjchem-788	7	25	september	september	PROPN
eurjchem-788	7	26	2013	2013	NUM
eurjchem-788	7	27	keywords	keyword	VERB
eurjchem-788	7	28	some	some	DET
eurjchem-788	7	29	new	new	ADJ
eurjchem-788	7	30	aminothieno[2,3‐b]quinolinones	aminothieno[2,3‐b]quinolinone	NOUN
eurjchem-788	7	31	and	and	CCONJ
eurjchem-788	7	32	tacrine	tacrine	ADJ
eurjchem-788	7	33	analogues	analogue	NOUN
eurjchem-788	7	34	derivatives	derivative	NOUN
eurjchem-788	7	35	were	be	AUX
eurjchem-788	7	36	synthesized	synthesize	VERB
eurjchem-788	7	37	in	in	ADP
eurjchem-788	7	38	high	high	ADJ
eurjchem-788	7	39	yield	yield	NOUN
eurjchem-788	7	40	with	with	ADP
eurjchem-788	7	41	acid	acid	ADJ
eurjchem-788	7	42	activated	activate	VERB
eurjchem-788	7	43	bentonite	bentonite	NOUN
eurjchem-788	7	44	as	as	ADP
eurjchem-788	7	45	a	a	DET
eurjchem-788	7	46	catalyst	catalyst	NOUN
eurjchem-788	7	47	via	via	ADP
eurjchem-788	7	48	the	the	DET
eurjchem-788	7	49	friedländer	friedländer	NOUN
eurjchem-788	7	50	condensation	condensation	NOUN
eurjchem-788	7	51	reactions	reaction	NOUN
eurjchem-788	7	52	between	between	ADP
eurjchem-788	7	53	2‐aminothiophene‐3‐carbonitrile	2‐aminothiophene‐3‐carbonitrile	ADJ
eurjchem-788	7	54	and	and	CCONJ
eurjchem-788	7	55	ketones	ketone	NOUN
eurjchem-788	7	56	.	.	PUNCT
eurjchem-788	8	1	the	the	DET
eurjchem-788	8	2	structure	structure	NOUN
eurjchem-788	8	3	elucidation	elucidation	NOUN
eurjchem-788	8	4	of	of	ADP
eurjchem-788	8	5	compounds	compound	NOUN
eurjchem-788	8	6	was	be	AUX
eurjchem-788	8	7	done	do	VERB
eurjchem-788	8	8	by	by	ADP
eurjchem-788	8	9	ft‐ir	ft‐ir	NOUN
eurjchem-788	8	10	,	,	PUNCT
eurjchem-788	8	11	nmr	nmr	NOUN
eurjchem-788	8	12	spectroscopy	spectroscopy	NOUN
eurjchem-788	8	13	and	and	CCONJ
eurjchem-788	8	14	microanalytical	microanalytical	ADJ
eurjchem-788	8	15	elemental	elemental	ADJ
eurjchem-788	8	16	data	datum	NOUN
eurjchem-788	8	17	.	.	PUNCT
eurjchem-788	9	1	ketones	ketone	NOUN
eurjchem-788	9	2	bentonite	bentonite	NOUN
eurjchem-788	9	3	tacrine	tacrine	ADJ
eurjchem-788	9	4	analogues	analogue	NOUN
eurjchem-788	9	5	friedlander	friedlander	NOUN
eurjchem-788	9	6	reaction	reaction	NOUN
eurjchem-788	9	7	2‐aminothiophene‐3‐carbonitrile	2‐aminothiophene‐3‐carbonitrile	PROPN
eurjchem-788	9	8	4‐aminothieno[2,3‐b]quinolinones	4‐aminothieno[2,3‐b]quinolinones	NUM
eurjchem-788	9	9	1	1	X
eurjchem-788	9	10	.	.	PUNCT
eurjchem-788	9	11	introduction	introduction	NOUN
eurjchem-788	9	12	tacrine	tacrine	NOUN
eurjchem-788	9	13	(	(	PUNCT
eurjchem-788	9	14	figure	figure	NOUN
eurjchem-788	9	15	1	1	NUM
eurjchem-788	9	16	)	)	PUNCT
eurjchem-788	9	17	sold	sell	VERB
eurjchem-788	9	18	under	under	ADP
eurjchem-788	9	19	the	the	DET
eurjchem-788	9	20	name	name	NOUN
eurjchem-788	9	21	gognex	gognex	NOUN
eurjchem-788	9	22	has	have	AUX
eurjchem-788	9	23	been	be	AUX
eurjchem-788	9	24	the	the	DET
eurjchem-788	9	25	first	first	ADJ
eurjchem-788	9	26	drug	drug	NOUN
eurjchem-788	9	27	that	that	PRON
eurjchem-788	9	28	proved	prove	VERB
eurjchem-788	9	29	to	to	PART
eurjchem-788	9	30	have	have	VERB
eurjchem-788	9	31	a	a	DET
eurjchem-788	9	32	beneficial	beneficial	ADJ
eurjchem-788	9	33	effect	effect	NOUN
eurjchem-788	9	34	on	on	ADP
eurjchem-788	9	35	cognition	cognition	NOUN
eurjchem-788	9	36	in	in	ADP
eurjchem-788	9	37	patients	patient	NOUN
eurjchem-788	9	38	with	with	ADP
eurjchem-788	9	39	alzheimer	alzheimer	PROPN
eurjchem-788	9	40	's	's	PART
eurjchem-788	9	41	disease	disease	NOUN
eurjchem-788	9	42	(	(	PUNCT
eurjchem-788	9	43	ad	ad	NOUN
eurjchem-788	9	44	)	)	PUNCT
eurjchem-788	10	1	[	[	X
eurjchem-788	10	2	1,2	1,2	NUM
eurjchem-788	10	3	]	]	PUNCT
eurjchem-788	10	4	.	.	PUNCT
eurjchem-788	11	1	however	however	ADV
eurjchem-788	11	2	this	this	DET
eurjchem-788	11	3	drug	drug	NOUN
eurjchem-788	11	4	is	be	AUX
eurjchem-788	11	5	not	not	PART
eurjchem-788	11	6	used	use	VERB
eurjchem-788	11	7	anymore	anymore	ADV
eurjchem-788	11	8	due	due	ADP
eurjchem-788	11	9	to	to	ADP
eurjchem-788	11	10	its	its	PRON
eurjchem-788	11	11	side	side	NOUN
eurjchem-788	11	12	effects	effect	NOUN
eurjchem-788	11	13	such	such	ADJ
eurjchem-788	11	14	as	as	ADP
eurjchem-788	11	15	hepatotoxicity	hepatotoxicity	NOUN
eurjchem-788	11	16	[	[	X
eurjchem-788	11	17	3,4	3,4	NUM
eurjchem-788	11	18	]	]	PUNCT
eurjchem-788	11	19	.	.	PUNCT
eurjchem-788	12	1	in	in	ADP
eurjchem-788	12	2	order	order	NOUN
eurjchem-788	12	3	to	to	PART
eurjchem-788	12	4	investigate	investigate	VERB
eurjchem-788	12	5	the	the	DET
eurjchem-788	12	6	biological	biological	ADJ
eurjchem-788	12	7	effects	effect	NOUN
eurjchem-788	12	8	of	of	ADP
eurjchem-788	12	9	structurally	structurally	ADV
eurjchem-788	12	10	modified	modify	VERB
eurjchem-788	12	11	tacrine	tacrine	NOUN
eurjchem-788	12	12	and	and	CCONJ
eurjchem-788	12	13	as	as	ADP
eurjchem-788	12	14	an	an	DET
eurjchem-788	12	15	extension	extension	NOUN
eurjchem-788	12	16	of	of	ADP
eurjchem-788	12	17	our	our	PRON
eurjchem-788	12	18	efforts	effort	NOUN
eurjchem-788	12	19	towards	towards	ADP
eurjchem-788	12	20	the	the	DET
eurjchem-788	12	21	facile	facile	ADJ
eurjchem-788	12	22	synthesis	synthesis	NOUN
eurjchem-788	12	23	of	of	ADP
eurjchem-788	12	24	heterocycles	heterocycle	NOUN
eurjchem-788	12	25	containing	contain	VERB
eurjchem-788	12	26	thiophene	thiophene	NOUN
eurjchem-788	12	27	ring	ring	NOUN
eurjchem-788	12	28	moiety	moiety	NOUN
eurjchem-788	12	29	[	[	X
eurjchem-788	12	30	5,6	5,6	NUM
eurjchem-788	12	31	]	]	PUNCT
eurjchem-788	12	32	.	.	PUNCT
eurjchem-788	13	1	we	we	PRON
eurjchem-788	13	2	report	report	VERB
eurjchem-788	13	3	here	here	ADV
eurjchem-788	13	4	the	the	DET
eurjchem-788	13	5	synthesis	synthesis	NOUN
eurjchem-788	13	6	of	of	ADP
eurjchem-788	13	7	series	series	NOUN
eurjchem-788	13	8	of	of	ADP
eurjchem-788	13	9	thiophene	thiophene	NOUN
eurjchem-788	13	10	analogues	analogue	NOUN
eurjchem-788	13	11	,	,	PUNCT
eurjchem-788	13	12	since	since	SCONJ
eurjchem-788	13	13	it	it	PRON
eurjchem-788	13	14	is	be	AUX
eurjchem-788	13	15	widely	widely	ADV
eurjchem-788	13	16	recognized	recognize	VERB
eurjchem-788	13	17	that	that	SCONJ
eurjchem-788	13	18	thiophene	thiophene	NOUN
eurjchem-788	13	19	ring	ring	NOUN
eurjchem-788	13	20	is	be	AUX
eurjchem-788	13	21	a	a	DET
eurjchem-788	13	22	bioisostere	bioisostere	NOUN
eurjchem-788	13	23	of	of	ADP
eurjchem-788	13	24	benzene	benzene	NOUN
eurjchem-788	13	25	.	.	PUNCT
eurjchem-788	14	1	2‐aminothiophene‐3‐carbonitrile	2‐aminothiophene‐3‐carbonitrile	ADJ
eurjchem-788	14	2	,	,	PUNCT
eurjchem-788	14	3	1	1	NUM
eurjchem-788	14	4	,	,	PUNCT
eurjchem-788	14	5	which	which	PRON
eurjchem-788	14	6	were	be	AUX
eurjchem-788	14	7	found	find	VERB
eurjchem-788	14	8	to	to	PART
eurjchem-788	14	9	possess	possess	VERB
eurjchem-788	14	10	an	an	DET
eurjchem-788	14	11	extensive	extensive	ADJ
eurjchem-788	14	12	spectrum	spectrum	NOUN
eurjchem-788	14	13	of	of	ADP
eurjchem-788	14	14	pharmacological	pharmacological	ADJ
eurjchem-788	14	15	activities	activity	NOUN
eurjchem-788	14	16	[	[	X
eurjchem-788	14	17	7,8‐10	7,8‐10	NUM
eurjchem-788	14	18	]	]	PUNCT
eurjchem-788	14	19	,	,	PUNCT
eurjchem-788	14	20	were	be	AUX
eurjchem-788	14	21	chosen	choose	VERB
eurjchem-788	14	22	as	as	ADP
eurjchem-788	14	23	synthon	synthon	ADJ
eurjchem-788	14	24	for	for	ADP
eurjchem-788	14	25	the	the	DET
eurjchem-788	14	26	synthesis	synthesis	NOUN
eurjchem-788	14	27	of	of	ADP
eurjchem-788	14	28	4‐aminothienoquinolinones	4‐aminothienoquinolinone	NOUN
eurjchem-788	14	29	2	2	NUM
eurjchem-788	14	30	and	and	CCONJ
eurjchem-788	14	31	thienotacrine	thienotacrine	NOUN
eurjchem-788	14	32	,	,	PUNCT
eurjchem-788	14	33	3	3	NUM
eurjchem-788	14	34	.	.	NOUN
eurjchem-788	14	35	2	2	NUM
eurjchem-788	14	36	.	.	X
eurjchem-788	14	37	experimental	experimental	ADJ
eurjchem-788	14	38	2.1	2.1	NUM
eurjchem-788	14	39	.	.	PUNCT
eurjchem-788	15	1	instrumentation	instrumentation	NOUN
eurjchem-788	15	2	melting	melting	NOUN
eurjchem-788	15	3	points	point	NOUN
eurjchem-788	15	4	were	be	AUX
eurjchem-788	15	5	taken	take	VERB
eurjchem-788	15	6	with	with	ADP
eurjchem-788	15	7	a	a	DET
eurjchem-788	15	8	kofler	kofler	NOUN
eurjchem-788	15	9	hot	hot	ADJ
eurjchem-788	15	10	staged	stage	VERB
eurjchem-788	15	11	apparatus	apparatus	NOUN
eurjchem-788	15	12	and	and	CCONJ
eurjchem-788	15	13	are	be	AUX
eurjchem-788	15	14	uncorrected	uncorrecte	VERB
eurjchem-788	15	15	.	.	PUNCT
eurjchem-788	16	1	all	all	DET
eurjchem-788	16	2	reactions	reaction	NOUN
eurjchem-788	16	3	were	be	AUX
eurjchem-788	16	4	monitored	monitor	VERB
eurjchem-788	16	5	by	by	ADP
eurjchem-788	16	6	thin	thin	ADJ
eurjchem-788	16	7	layer	layer	NOUN
eurjchem-788	16	8	chromatography	chromatography	NOUN
eurjchem-788	16	9	(	(	PUNCT
eurjchem-788	16	10	tlc	tlc	NOUN
eurjchem-788	16	11	)	)	PUNCT
eurjchem-788	16	12	.	.	PUNCT
eurjchem-788	17	1	ir	ir	PROPN
eurjchem-788	17	2	spectra	spectra	PROPN
eurjchem-788	17	3	were	be	AUX
eurjchem-788	17	4	determined	determine	VERB
eurjchem-788	17	5	with	with	ADP
eurjchem-788	17	6	a	a	DET
eurjchem-788	17	7	perkin	perkin	PROPN
eurjchem-788	17	8	elmer	elmer	PROPN
eurjchem-788	17	9	1600	1600	NUM
eurjchem-788	17	10	series	series	PROPN
eurjchem-788	17	11	ft‐ir	ft‐ir	NOUN
eurjchem-788	17	12	spectrometer	spectrometer	NOUN
eurjchem-788	17	13	.	.	PUNCT
eurjchem-788	18	1	1h	1h	NUM
eurjchem-788	18	2	and	and	CCONJ
eurjchem-788	18	3	13c	13c	NOUN
eurjchem-788	18	4	nmr	nmr	NOUN
eurjchem-788	18	5	spectra	spectra	NOUN
eurjchem-788	18	6	were	be	AUX
eurjchem-788	18	7	recorded	record	VERB
eurjchem-788	18	8	on	on	ADP
eurjchem-788	18	9	a	a	DET
eurjchem-788	18	10	varian‐unity	varian‐unity	NOUN
eurjchem-788	18	11	spectrometer	spectrometer	NOUN
eurjchem-788	18	12	at	at	ADP
eurjchem-788	18	13	300	300	NUM
eurjchem-788	18	14	mhz	mhz	NOUN
eurjchem-788	18	15	using	use	VERB
eurjchem-788	18	16	tms	tms	PROPN
eurjchem-788	18	17	as	as	ADP
eurjchem-788	18	18	an	an	DET
eurjchem-788	18	19	internal	internal	ADJ
eurjchem-788	18	20	standard	standard	NOUN
eurjchem-788	18	21	.	.	PUNCT
eurjchem-788	19	1	elemental	elemental	ADJ
eurjchem-788	19	2	analyses	analysis	NOUN
eurjchem-788	19	3	were	be	AUX
eurjchem-788	19	4	determined	determine	VERB
eurjchem-788	19	5	using	use	VERB
eurjchem-788	19	6	a	a	DET
eurjchem-788	19	7	elementar	elementar	NOUN
eurjchem-788	19	8	vario	vario	NOUN
eurjchem-788	19	9	ei	ei	PROPN
eurjchem-788	19	10	iii	iii	PROPN
eurjchem-788	19	11	elemental	elemental	PROPN
eurjchem-788	19	12	analyser	analyser	NOUN
eurjchem-788	19	13	2.2	2.2	NUM
eurjchem-788	19	14	.	.	PUNCT
eurjchem-788	20	1	synthesis	synthesis	NOUN
eurjchem-788	20	2	2.2.1	2.2.1	NUM
eurjchem-788	20	3	.	.	PUNCT
eurjchem-788	20	4	general	general	ADJ
eurjchem-788	20	5	procedure	procedure	NOUN
eurjchem-788	20	6	for	for	ADP
eurjchem-788	20	7	the	the	DET
eurjchem-788	20	8	synthesis	synthesis	NOUN
eurjchem-788	20	9	of	of	ADP
eurjchem-788	20	10	starting	start	VERB
eurjchem-788	20	11	material	material	NOUN
eurjchem-788	20	12	substituted	substitute	VERB
eurjchem-788	20	13	2‐aminothiophene‐3‐carbonitrile	2‐aminothiophene‐3‐carbonitrile	PROPN
eurjchem-788	20	14	(	(	PUNCT
eurjchem-788	20	15	1	1	NUM
eurjchem-788	20	16	)	)	PUNCT
eurjchem-788	20	17	in	in	ADP
eurjchem-788	20	18	a	a	DET
eurjchem-788	20	19	typical	typical	ADJ
eurjchem-788	20	20	experiment	experiment	NOUN
eurjchem-788	20	21	,	,	PUNCT
eurjchem-788	20	22	ketone	ketone	NOUN
eurjchem-788	20	23	(	(	PUNCT
eurjchem-788	20	24	0.10	0.10	NUM
eurjchem-788	20	25	mol	mol	NOUN
eurjchem-788	20	26	)	)	PUNCT
eurjchem-788	20	27	and	and	CCONJ
eurjchem-788	20	28	malononitrile	malononitrile	NOUN
eurjchem-788	20	29	(	(	PUNCT
eurjchem-788	20	30	0.10	0.10	NUM
eurjchem-788	20	31	mol	mol	NOUN
eurjchem-788	20	32	)	)	PUNCT
eurjchem-788	20	33	were	be	AUX
eurjchem-788	20	34	dissolved	dissolve	VERB
eurjchem-788	20	35	in	in	ADP
eurjchem-788	20	36	200	200	NUM
eurjchem-788	20	37	ml	ml	NOUN
eurjchem-788	20	38	of	of	ADP
eurjchem-788	20	39	absolute	absolute	ADJ
eurjchem-788	20	40	ethanol	ethanol	NOUN
eurjchem-788	20	41	.	.	PUNCT
eurjchem-788	21	1	sulphur	sulphur	NOUN
eurjchem-788	21	2	powder	powder	NOUN
eurjchem-788	21	3	(	(	PUNCT
eurjchem-788	21	4	0.11	0.11	NUM
eurjchem-788	21	5	mol	mol	NOUN
eurjchem-788	21	6	)	)	PUNCT
eurjchem-788	21	7	and	and	CCONJ
eurjchem-788	21	8	morpholine	morpholine	ADJ
eurjchem-788	21	9	(	(	PUNCT
eurjchem-788	21	10	20	20	NUM
eurjchem-788	21	11	ml	ml	NOUN
eurjchem-788	21	12	)	)	PUNCT
eurjchem-788	21	13	were	be	AUX
eurjchem-788	21	14	added	add	VERB
eurjchem-788	21	15	.	.	PUNCT
eurjchem-788	22	1	the	the	DET
eurjchem-788	22	2	mixture	mixture	NOUN
eurjchem-788	22	3	was	be	AUX
eurjchem-788	22	4	heated	heat	VERB
eurjchem-788	22	5	at	at	ADP
eurjchem-788	22	6	50	50	NUM
eurjchem-788	22	7	°	°	NOUN
eurjchem-788	22	8	c	c	NOUN
eurjchem-788	22	9	during	during	ADP
eurjchem-788	22	10	3	3	NUM
eurjchem-788	22	11	hours	hour	NOUN
eurjchem-788	22	12	and	and	CCONJ
eurjchem-788	22	13	then	then	ADV
eurjchem-788	22	14	was	be	AUX
eurjchem-788	22	15	cooled	cool	VERB
eurjchem-788	22	16	at	at	ADP
eurjchem-788	22	17	room	room	NOUN
eurjchem-788	22	18	temperature	temperature	NOUN
eurjchem-788	22	19	.	.	PUNCT
eurjchem-788	23	1	the	the	DET
eurjchem-788	23	2	mixture	mixture	NOUN
eurjchem-788	23	3	poured	pour	VERB
eurjchem-788	23	4	into	into	ADP
eurjchem-788	23	5	300	300	NUM
eurjchem-788	23	6	ml	ml	NOUN
eurjchem-788	23	7	ice‐water	ice‐water	NOUN
eurjchem-788	23	8	.	.	PUNCT
eurjchem-788	24	1	the	the	DET
eurjchem-788	24	2	filtered	filter	VERB
eurjchem-788	24	3	precipitate	precipitate	NOUN
eurjchem-788	24	4	was	be	AUX
eurjchem-788	24	5	washed	wash	VERB
eurjchem-788	24	6	with	with	ADP
eurjchem-788	24	7	cold	cold	ADJ
eurjchem-788	24	8	water	water	NOUN
eurjchem-788	24	9	,	,	PUNCT
eurjchem-788	24	10	dried	dry	VERB
eurjchem-788	24	11	and	and	CCONJ
eurjchem-788	24	12	then	then	ADV
eurjchem-788	24	13	recrystallized	recrystallize	VERB
eurjchem-788	24	14	in	in	ADP
eurjchem-788	24	15	suitable	suitable	ADJ
eurjchem-788	24	16	solvent	solvent	NOUN
eurjchem-788	24	17	(	(	PUNCT
eurjchem-788	24	18	scheme	scheme	NOUN
eurjchem-788	24	19	1	1	NUM
eurjchem-788	24	20	)	)	PUNCT
eurjchem-788	24	21	.	.	PUNCT
eurjchem-788	25	1	2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile	2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile	NUM
eurjchem-788	25	2	(	(	PUNCT
eurjchem-788	25	3	1a	1a	NOUN
eurjchem-788	25	4	):	):	PUNCT
eurjchem-788	25	5	color	color	NOUN
eurjchem-788	25	6	:	:	PUNCT
eurjchem-788	25	7	ocher	ocher	ADJ
eurjchem-788	25	8	needles	needle	NOUN
eurjchem-788	25	9	.	.	PUNCT
eurjchem-788	26	1	yield	yield	NOUN
eurjchem-788	26	2	:	:	PUNCT
eurjchem-788	26	3	92	92	NUM
eurjchem-788	26	4	%	%	NOUN
eurjchem-788	26	5	.	.	PUNCT
eurjchem-788	27	1	m.p	m.p	PROPN
eurjchem-788	27	2	.	.	PROPN
eurjchem-788	27	3	:	:	PUNCT
eurjchem-788	28	1	145‐147	145‐147	NUM
eurjchem-788	28	2	°	°	PROPN
eurjchem-788	28	3	c	c	PROPN
eurjchem-788	28	4	.	.	PUNCT
eurjchem-788	29	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	29	2	(	(	PUNCT
eurjchem-788	29	3	chcl3	chcl3	PROPN
eurjchem-788	29	4	,	,	PUNCT
eurjchem-788	29	5	ν	ν	PROPN
eurjchem-788	29	6	,	,	PUNCT
eurjchem-788	29	7	cm‐1	cm‐1	PROPN
eurjchem-788	29	8	):	):	PUNCT
eurjchem-788	29	9	3433	3433	NUM
eurjchem-788	29	10	,	,	PUNCT
eurjchem-788	29	11	3326	3326	NUM
eurjchem-788	29	12	ν(nh	ν(nh	NOUN
eurjchem-788	29	13	)	)	PUNCT
eurjchem-788	29	14	(	(	PUNCT
eurjchem-788	29	15	nh2	nh2	PROPN
eurjchem-788	29	16	)	)	PUNCT
eurjchem-788	29	17	,	,	PUNCT
eurjchem-788	29	18	2198	2198	NUM
eurjchem-788	29	19	ν(cn	ν(cn	NUM
eurjchem-788	29	20	)	)	PUNCT
eurjchem-788	29	21	,	,	PUNCT
eurjchem-788	29	22	1615	1615	NUM
eurjchem-788	29	23	δ(nh	δ(nh	NOUN
eurjchem-788	29	24	)	)	PUNCT
eurjchem-788	29	25	.	.	PUNCT
eurjchem-788	30	1	1h	1h	NUM
eurjchem-788	30	2	nmr	nmr	NOUN
eurjchem-788	30	3	(	(	PUNCT
eurjchem-788	30	4	300	300	NUM
eurjchem-788	30	5	mhz	mhz	NOUN
eurjchem-788	30	6	,	,	PUNCT
eurjchem-788	30	7	dmso‐d6	dmso‐d6	NOUN
eurjchem-788	30	8	+	+	CCONJ
eurjchem-788	30	9	cdcl3	cdcl3	PROPN
eurjchem-788	30	10	,	,	PUNCT
eurjchem-788	30	11	δ	δ	PROPN
eurjchem-788	30	12	,	,	PUNCT
eurjchem-788	30	13	ppm	ppm	NUM
eurjchem-788	30	14	):	):	PUNCT
eurjchem-788	30	15	4.62	4.62	NUM
eurjchem-788	30	16	(	(	PUNCT
eurjchem-788	30	17	s	s	PROPN
eurjchem-788	30	18	,	,	PUNCT
eurjchem-788	30	19	br	br	PROPN
eurjchem-788	30	20	,	,	PUNCT
eurjchem-788	30	21	2h	2h	NUM
eurjchem-788	30	22	,	,	PUNCT
eurjchem-788	30	23	nh2	nh2	PROPN
eurjchem-788	30	24	)	)	PUNCT
eurjchem-788	30	25	,	,	PUNCT
eurjchem-788	30	26	2.53	2.53	NUM
eurjchem-788	30	27	(	(	PUNCT
eurjchem-788	30	28	m	m	PROPN
eurjchem-788	30	29	,	,	PUNCT
eurjchem-788	30	30	4h	4h	NOUN
eurjchem-788	30	31	,	,	PUNCT
eurjchem-788	30	32	ch2	ch2	PROPN
eurjchem-788	30	33	)	)	PUNCT
eurjchem-788	30	34	,	,	PUNCT
eurjchem-788	30	35	1.76	1.76	NUM
eurjchem-788	30	36	(	(	PUNCT
eurjchem-788	30	37	m	m	PROPN
eurjchem-788	30	38	,	,	PUNCT
eurjchem-788	30	39	4h	4h	NOUN
eurjchem-788	30	40	,	,	PUNCT
eurjchem-788	30	41	ch2	ch2	PROPN
eurjchem-788	30	42	)	)	PUNCT
eurjchem-788	30	43	.	.	PUNCT
eurjchem-788	31	1	13c	13c	NOUN
eurjchem-788	31	2	nmr	nmr	NOUN
eurjchem-788	31	3	(	(	PUNCT
eurjchem-788	31	4	75	75	NUM
eurjchem-788	31	5	mhz	mhz	NOUN
eurjchem-788	31	6	,	,	PUNCT
eurjchem-788	31	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	31	8	+	+	CCONJ
eurjchem-788	31	9	cdcl3	cdcl3	PROPN
eurjchem-788	31	10	,	,	PUNCT
eurjchem-788	31	11	δ	δ	PROPN
eurjchem-788	31	12	,	,	PUNCT
eurjchem-788	31	13	ppm	ppm	NOUN
eurjchem-788	31	14	):	):	PUNCT
eurjchem-788	31	15	158.1	158.1	NUM
eurjchem-788	31	16	(	(	PUNCT
eurjchem-788	31	17	1c	1c	NOUN
eurjchem-788	31	18	,	,	PUNCT
eurjchem-788	31	19	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	31	20	)	)	PUNCT
eurjchem-788	31	21	,	,	PUNCT
eurjchem-788	31	22	133.2	133.2	NUM
eurjchem-788	31	23	(	(	PUNCT
eurjchem-788	31	24	1c	1c	NOUN
eurjchem-788	31	25	,	,	PUNCT
eurjchem-788	31	26	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	31	27	)	)	PUNCT
eurjchem-788	31	28	,	,	PUNCT
eurjchem-788	31	29	120.4	120.4	NUM
eurjchem-788	31	30	(	(	PUNCT
eurjchem-788	31	31	1c	1c	NOUN
eurjchem-788	31	32	,	,	PUNCT
eurjchem-788	31	33	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	31	34	)	)	PUNCT
eurjchem-788	31	35	,	,	PUNCT
eurjchem-788	31	36	116.1	116.1	NUM
eurjchem-788	31	37	(	(	PUNCT
eurjchem-788	31	38	1c	1c	X
eurjchem-788	31	39	,	,	PUNCT
eurjchem-788	31	40	cn	cn	PROPN
eurjchem-788	31	41	)	)	PUNCT
eurjchem-788	31	42	,	,	PUNCT
eurjchem-788	31	43	113.2	113.2	NUM
eurjchem-788	31	44	(	(	PUNCT
eurjchem-788	31	45	1c	1c	NOUN
eurjchem-788	31	46	,	,	PUNCT
eurjchem-788	31	47	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	31	48	)	)	PUNCT
eurjchem-788	31	49	,	,	PUNCT
eurjchem-788	31	50	24.3	24.3	NUM
eurjchem-788	31	51	(	(	PUNCT
eurjchem-788	31	52	1c	1c	NOUN
eurjchem-788	31	53	,	,	PUNCT
eurjchem-788	31	54	‐ch2‐	‐ch2‐	PROPN
eurjchem-788	31	55	)	)	PUNCT
eurjchem-788	31	56	,	,	PUNCT
eurjchem-788	31	57	23.8	23.8	NUM
eurjchem-788	31	58	(	(	PUNCT
eurjchem-788	31	59	1c	1c	NOUN
eurjchem-788	31	60	,	,	PUNCT
eurjchem-788	31	61	‐ch2‐	‐ch2‐	PROPN
eurjchem-788	31	62	)	)	PUNCT
eurjchem-788	31	63	,	,	PUNCT
eurjchem-788	31	64	22.7	22.7	NUM
eurjchem-788	31	65	(	(	PUNCT
eurjchem-788	31	66	1c	1c	NOUN
eurjchem-788	31	67	,	,	PUNCT
eurjchem-788	31	68	‐ch2‐	‐ch2‐	PROPN
eurjchem-788	31	69	)	)	PUNCT
eurjchem-788	31	70	,	,	PUNCT
eurjchem-788	31	71	21.8	21.8	NUM
eurjchem-788	31	72	(	(	PUNCT
eurjchem-788	31	73	1c	1c	NOUN
eurjchem-788	31	74	,	,	PUNCT
eurjchem-788	31	75	‐ch2‐	‐ch2‐	PROPN
eurjchem-788	31	76	)	)	PUNCT
eurjchem-788	31	77	.	.	PUNCT
eurjchem-788	32	1	2‐amino‐4,5‐dimethylthiophene‐3‐carbonitrile	2‐amino‐4,5‐dimethylthiophene‐3‐carbonitrile	NUM
eurjchem-788	32	2	(	(	PUNCT
eurjchem-788	32	3	1b	1b	NUM
eurjchem-788	32	4	):	):	PUNCT
eurjchem-788	32	5	color	color	NOUN
eurjchem-788	32	6	:	:	PUNCT
eurjchem-788	32	7	red‐brownish	red‐brownish	ADJ
eurjchem-788	32	8	.	.	PUNCT
eurjchem-788	32	9	yield	yield	NOUN
eurjchem-788	32	10	:	:	PUNCT
eurjchem-788	32	11	67	67	NUM
eurjchem-788	32	12	%	%	NOUN
eurjchem-788	32	13	.	.	PUNCT
eurjchem-788	33	1	m.p	m.p	PROPN
eurjchem-788	33	2	.	.	PROPN
eurjchem-788	33	3	:	:	PUNCT
eurjchem-788	34	1	140‐142	140‐142	NUM
eurjchem-788	34	2	°	°	NUM
eurjchem-788	34	3	c	c	X
eurjchem-788	34	4	.	.	PUNCT
eurjchem-788	34	5	ft‐ir	ft‐ir	NOUN
eurjchem-788	34	6	(	(	PUNCT
eurjchem-788	34	7	chcl3	chcl3	PROPN
eurjchem-788	34	8	,	,	PUNCT
eurjchem-788	34	9	ν	ν	PROPN
eurjchem-788	34	10	,	,	PUNCT
eurjchem-788	34	11	cm‐1	cm‐1	PROPN
eurjchem-788	34	12	):	):	PUNCT
eurjchem-788	34	13	3421	3421	NUM
eurjchem-788	34	14	,	,	PUNCT
eurjchem-788	34	15	3309	3309	NUM
eurjchem-788	34	16	(nh2	(nh2	NOUN
eurjchem-788	34	17	)	)	PUNCT
eurjchem-788	34	18	(	(	PUNCT
eurjchem-788	34	19	nh2	nh2	PROPN
eurjchem-788	34	20	)	)	PUNCT
eurjchem-788	34	21	,	,	PUNCT
eurjchem-788	34	22	2212	2212	NUM
eurjchem-788	34	23	(cn	(cn	NOUN
eurjchem-788	34	24	)	)	PUNCT
eurjchem-788	34	25	,	,	PUNCT
eurjchem-788	34	26	1632	1632	NUM
eurjchem-788	34	27	(nh	(nh	PROPN
eurjchem-788	34	28	)	)	PUNCT
eurjchem-788	34	29	(	(	PUNCT
eurjchem-788	34	30	nh2	nh2	PROPN
eurjchem-788	34	31	)	)	PUNCT
eurjchem-788	34	32	.	.	PUNCT
eurjchem-788	35	1	1h	1h	NUM
eurjchem-788	35	2	nmr	nmr	NOUN
eurjchem-788	35	3	(	(	PUNCT
eurjchem-788	35	4	300	300	NUM
eurjchem-788	35	5	mhz	mhz	NOUN
eurjchem-788	35	6	,	,	PUNCT
eurjchem-788	35	7	dmso‐d6	dmso‐d6	NOUN
eurjchem-788	35	8	+	+	CCONJ
eurjchem-788	35	9	cdcl3	cdcl3	PROPN
eurjchem-788	35	10	,	,	PUNCT
eurjchem-788	35	11	δ	δ	PROPN
eurjchem-788	35	12	,	,	PUNCT
eurjchem-788	35	13	ppm	ppm	NUM
eurjchem-788	35	14	):	):	PUNCT
eurjchem-788	35	15	4.62	4.62	NUM
eurjchem-788	35	16	(	(	PUNCT
eurjchem-788	35	17	s	s	PROPN
eurjchem-788	35	18	,	,	PUNCT
eurjchem-788	35	19	br	br	PROPN
eurjchem-788	35	20	,	,	PUNCT
eurjchem-788	35	21	2h	2h	NUM
eurjchem-788	35	22	,	,	PUNCT
eurjchem-788	35	23	nh2	nh2	PROPN
eurjchem-788	35	24	)	)	PUNCT
eurjchem-788	35	25	,	,	PUNCT
eurjchem-788	35	26	2.16	2.16	NUM
eurjchem-788	35	27	(	(	PUNCT
eurjchem-788	35	28	s	s	PROPN
eurjchem-788	35	29	,	,	PUNCT
eurjchem-788	35	30	3h	3h	NUM
eurjchem-788	35	31	,	,	PUNCT
eurjchem-788	35	32	ch3	ch3	PROPN
eurjchem-788	35	33	)	)	PUNCT
eurjchem-788	35	34	,	,	PUNCT
eurjchem-788	35	35	2.07	2.07	NUM
eurjchem-788	35	36	(	(	PUNCT
eurjchem-788	35	37	s	s	PROPN
eurjchem-788	35	38	,	,	PUNCT
eurjchem-788	35	39	3h	3h	NUM
eurjchem-788	35	40	,	,	PUNCT
eurjchem-788	35	41	ch3	ch3	PROPN
eurjchem-788	35	42	)	)	PUNCT
eurjchem-788	35	43	.	.	PUNCT
eurjchem-788	36	1	13c	13c	NOUN
eurjchem-788	36	2	nmr	nmr	NOUN
eurjchem-788	36	3	(	(	PUNCT
eurjchem-788	36	4	75	75	NUM
eurjchem-788	36	5	mhz	mhz	NOUN
eurjchem-788	36	6	,	,	PUNCT
eurjchem-788	36	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	36	8	+	+	CCONJ
eurjchem-788	36	9	cdcl3	cdcl3	PROPN
eurjchem-788	36	10	,	,	PUNCT
eurjchem-788	36	11	δ	δ	PROPN
eurjchem-788	36	12	,	,	PUNCT
eurjchem-788	36	13	ppm	ppm	NUM
eurjchem-788	36	14	):	):	PUNCT
eurjchem-788	36	15	159.1	159.1	NUM
eurjchem-788	36	16	(	(	PUNCT
eurjchem-788	36	17	1c	1c	NOUN
eurjchem-788	36	18	,	,	PUNCT
eurjchem-788	36	19	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	36	20	)	)	PUNCT
eurjchem-788	36	21	,	,	PUNCT
eurjchem-788	36	22	129.6	129.6	NUM
eurjchem-788	36	23	(	(	PUNCT
eurjchem-788	36	24	1c	1c	NOUN
eurjchem-788	36	25	,	,	PUNCT
eurjchem-788	36	26	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	36	27	)	)	PUNCT
eurjchem-788	36	28	,	,	PUNCT
eurjchem-788	36	29	120.2	120.2	NUM
eurjchem-788	36	30	(	(	PUNCT
eurjchem-788	36	31	1c	1c	NOUN
eurjchem-788	36	32	,	,	PUNCT
eurjchem-788	36	33	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	36	34	)	)	PUNCT
eurjchem-788	36	35	,	,	PUNCT
eurjchem-788	36	36	115.9	115.9	NUM
eurjchem-788	36	37	(	(	PUNCT
eurjchem-788	36	38	1c	1c	NOUN
eurjchem-788	36	39	,	,	PUNCT
eurjchem-788	36	40	cn	cn	PROPN
eurjchem-788	36	41	)	)	PUNCT
eurjchem-788	36	42	,	,	PUNCT
eurjchem-788	36	43	112.5	112.5	NUM
eurjchem-788	36	44	(	(	PUNCT
eurjchem-788	36	45	1c	1c	NOUN
eurjchem-788	36	46	,	,	PUNCT
eurjchem-788	36	47	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	36	48	)	)	PUNCT
eurjchem-788	36	49	,	,	PUNCT
eurjchem-788	36	50	12.7	12.7	NUM
eurjchem-788	36	51	(	(	PUNCT
eurjchem-788	36	52	1c	1c	X
eurjchem-788	36	53	,	,	PUNCT
eurjchem-788	36	54	ch3	ch3	PROPN
eurjchem-788	36	55	)	)	PUNCT
eurjchem-788	36	56	,	,	PUNCT
eurjchem-788	36	57	12.3	12.3	NUM
eurjchem-788	36	58	(	(	PUNCT
eurjchem-788	36	59	1c	1c	NOUN
eurjchem-788	36	60	,	,	PUNCT
eurjchem-788	36	61	ch3	ch3	PROPN
eurjchem-788	36	62	)	)	PUNCT
eurjchem-788	36	63	.	.	PUNCT
eurjchem-788	37	1	2‐amino‐4‐(4‐chlorophenyl)thiophene‐3‐carbonitrile	2‐amino‐4‐(4‐chlorophenyl)thiophene‐3‐carbonitrile	ADJ
eurjchem-788	37	2	(	(	PUNCT
eurjchem-788	37	3	1c	1c	NOUN
eurjchem-788	37	4	):	):	PUNCT
eurjchem-788	37	5	color	color	NOUN
eurjchem-788	37	6	:	:	PUNCT
eurjchem-788	37	7	orange	orange	ADJ
eurjchem-788	37	8	.	.	PUNCT
eurjchem-788	38	1	yield	yield	NOUN
eurjchem-788	38	2	:	:	PUNCT
eurjchem-788	38	3	88	88	NUM
eurjchem-788	38	4	%	%	NOUN
eurjchem-788	38	5	.	.	PUNCT
eurjchem-788	39	1	m.p	m.p	PROPN
eurjchem-788	39	2	.	.	PROPN
eurjchem-788	39	3	:	:	PUNCT
eurjchem-788	40	1	162‐164	162‐164	NUM
eurjchem-788	40	2	°	°	NUM
eurjchem-788	40	3	c	c	X
eurjchem-788	40	4	.	.	PUNCT
eurjchem-788	41	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	41	2	(	(	PUNCT
eurjchem-788	41	3	chcl3	chcl3	PROPN
eurjchem-788	41	4	,	,	PUNCT
eurjchem-788	41	5	ν	ν	PROPN
eurjchem-788	41	6	,	,	PUNCT
eurjchem-788	41	7	cm‐1	cm‐1	PROPN
eurjchem-788	41	8	):	):	PUNCT
eurjchem-788	41	9	3421	3421	NUM
eurjchem-788	41	10	,	,	PUNCT
eurjchem-788	41	11	3309	3309	NUM
eurjchem-788	41	12	(nh	(nh	PROPN
eurjchem-788	41	13	)	)	PUNCT
eurjchem-788	41	14	(	(	PUNCT
eurjchem-788	41	15	nh2	nh2	PROPN
eurjchem-788	41	16	)	)	PUNCT
eurjchem-788	41	17	,	,	PUNCT
eurjchem-788	41	18	2212	2212	NUM
eurjchem-788	41	19	(cn	(cn	NOUN
eurjchem-788	41	20	)	)	PUNCT
eurjchem-788	41	21	,	,	PUNCT
eurjchem-788	41	22	1638	1638	NUM
eurjchem-788	41	23	(nh	(nh	NOUN
eurjchem-788	41	24	)	)	PUNCT
eurjchem-788	41	25	(	(	PUNCT
eurjchem-788	41	26	nh2	nh2	PROPN
eurjchem-788	41	27	)	)	PUNCT
eurjchem-788	41	28	,	,	PUNCT
eurjchem-788	41	29	816	816	NUM
eurjchem-788	41	30	(	(	PUNCT
eurjchem-788	41	31	c‐cl	c‐cl	PROPN
eurjchem-788	41	32	)	)	PUNCT
eurjchem-788	41	33	,	,	PUNCT
eurjchem-788	41	34	766	766	NUM
eurjchem-788	41	35	(	(	PUNCT
eurjchem-788	41	36	disubstituted	disubstitute	VERB
eurjchem-788	41	37	phenyl	phenyl	NOUN
eurjchem-788	41	38	)	)	PUNCT
eurjchem-788	41	39	.	.	PUNCT
eurjchem-788	42	1	dridi	dridi	PROPN
eurjchem-788	42	2	et	et	PROPN
eurjchem-788	42	3	al	al	PROPN
eurjchem-788	42	4	.	.	PUNCT
eurjchem-788	42	5	/	/	SYM
eurjchem-788	42	6	european	european	PROPN
eurjchem-788	42	7	journal	journal	PROPN
eurjchem-788	42	8	of	of	ADP
eurjchem-788	42	9	chemistry	chemistry	NOUN
eurjchem-788	42	10	4	4	NUM
eurjchem-788	42	11	(	(	PUNCT
eurjchem-788	42	12	3	3	NUM
eurjchem-788	42	13	)	)	PUNCT
eurjchem-788	42	14	(	(	PUNCT
eurjchem-788	42	15	2013	2013	NUM
eurjchem-788	42	16	)	)	PUNCT
eurjchem-788	42	17	216‐219	216‐219	PROPN
eurjchem-788	42	18	217	217	NUM
eurjchem-788	42	19	s	s	NOUN
eurjchem-788	42	20	r2	r2	PROPN
eurjchem-788	42	21	r1	r1	PROPN
eurjchem-788	42	22	n	n	ADP
eurjchem-788	42	23	nh2	nh2	PROPN
eurjchem-788	42	24	s	s	PART
eurjchem-788	42	25	r2	r2	PROPN
eurjchem-788	42	26	r1	r1	PROPN
eurjchem-788	42	27	n	n	PRON
eurjchem-788	42	28	nh2	nh2	PROPN
eurjchem-788	42	29	r4	r4	PROPN
eurjchem-788	42	30	r3	r3	PROPN
eurjchem-788	42	31	o	o	NOUN
eurjchem-788	42	32	32	32	NUM
eurjchem-788	42	33	n	n	NUM
eurjchem-788	42	34	nh2	nh2	PROPN
eurjchem-788	42	35	tacrine	tacrine	NOUN
eurjchem-788	42	36	s	s	PROPN
eurjchem-788	42	37	r2	r2	PROPN
eurjchem-788	42	38	r1	r1	PROPN
eurjchem-788	42	39	cn	cn	PROPN
eurjchem-788	42	40	nh2	nh2	PROPN
eurjchem-788	42	41	1	1	NUM
eurjchem-788	42	42	figure	figure	NOUN
eurjchem-788	42	43	1	1	NUM
eurjchem-788	42	44	.	.	PUNCT
eurjchem-788	43	1	chemical	chemical	NOUN
eurjchem-788	43	2	structures	structure	NOUN
eurjchem-788	43	3	of	of	ADP
eurjchem-788	43	4	tacrine	tacrine	NOUN
eurjchem-788	43	5	,	,	PUNCT
eurjchem-788	43	6	starting	start	VERB
eurjchem-788	43	7	material	material	NOUN
eurjchem-788	43	8	1	1	NUM
eurjchem-788	43	9	and	and	CCONJ
eurjchem-788	43	10	the	the	DET
eurjchem-788	43	11	synthesized	synthesize	VERB
eurjchem-788	43	12	compounds	compound	NOUN
eurjchem-788	43	13	2	2	NUM
eurjchem-788	43	14	and	and	CCONJ
eurjchem-788	43	15	3	3	NUM
eurjchem-788	43	16	.	.	X
eurjchem-788	43	17	scheme	scheme	VERB
eurjchem-788	43	18	1	1	NUM
eurjchem-788	43	19	1h	1h	NUM
eurjchem-788	43	20	nmr	nmr	NOUN
eurjchem-788	43	21	(	(	PUNCT
eurjchem-788	43	22	300	300	NUM
eurjchem-788	43	23	mhz	mhz	NOUN
eurjchem-788	43	24	,	,	PUNCT
eurjchem-788	43	25	dmso‐d6	dmso‐d6	NOUN
eurjchem-788	43	26	+	+	CCONJ
eurjchem-788	43	27	cdcl3	cdcl3	PROPN
eurjchem-788	43	28	,	,	PUNCT
eurjchem-788	43	29	δ	δ	PROPN
eurjchem-788	43	30	,	,	PUNCT
eurjchem-788	43	31	ppm	ppm	NUM
eurjchem-788	43	32	):	):	PUNCT
eurjchem-788	43	33	7.32	7.32	NUM
eurjchem-788	43	34	(	(	PUNCT
eurjchem-788	43	35	d	d	PROPN
eurjchem-788	43	36	,	,	PUNCT
eurjchem-788	43	37	2h	2h	NUM
eurjchem-788	43	38	,	,	PUNCT
eurjchem-788	43	39	j	j	PROPN
eurjchem-788	43	40	=	=	SYM
eurjchem-788	43	41	8.5	8.5	NUM
eurjchem-788	43	42	hz	hz	NOUN
eurjchem-788	43	43	,	,	PUNCT
eurjchem-788	43	44	ar‐h	ar‐h	PROPN
eurjchem-788	43	45	)	)	PUNCT
eurjchem-788	43	46	,	,	PUNCT
eurjchem-788	43	47	7.04	7.04	NUM
eurjchem-788	43	48	(	(	PUNCT
eurjchem-788	43	49	d	d	PROPN
eurjchem-788	43	50	,	,	PUNCT
eurjchem-788	43	51	2h	2h	NUM
eurjchem-788	43	52	,	,	PUNCT
eurjchem-788	43	53	j	j	PROPN
eurjchem-788	43	54	=	=	SYM
eurjchem-788	43	55	8.5	8.5	NUM
eurjchem-788	43	56	hz	hz	NOUN
eurjchem-788	43	57	,	,	PUNCT
eurjchem-788	43	58	ar‐h	ar‐h	PROPN
eurjchem-788	43	59	)	)	PUNCT
eurjchem-788	43	60	,	,	PUNCT
eurjchem-788	43	61	6.87	6.87	NUM
eurjchem-788	43	62	(	(	PUNCT
eurjchem-788	43	63	s	s	PROPN
eurjchem-788	43	64	,	,	PUNCT
eurjchem-788	43	65	1h	1h	NUM
eurjchem-788	43	66	,	,	PUNCT
eurjchem-788	43	67	thienyl‐	thienyl‐	NOUN
eurjchem-788	43	68	h	h	NOUN
eurjchem-788	43	69	)	)	PUNCT
eurjchem-788	43	70	,	,	PUNCT
eurjchem-788	43	71	5.38	5.38	NUM
eurjchem-788	43	72	(	(	PUNCT
eurjchem-788	43	73	s	s	PROPN
eurjchem-788	43	74	,	,	PUNCT
eurjchem-788	43	75	br	br	PROPN
eurjchem-788	43	76	,	,	PUNCT
eurjchem-788	43	77	2h	2h	NUM
eurjchem-788	43	78	,	,	PUNCT
eurjchem-788	43	79	nh2	nh2	PROPN
eurjchem-788	43	80	)	)	PUNCT
eurjchem-788	43	81	.	.	PUNCT
eurjchem-788	44	1	13c	13c	NOUN
eurjchem-788	44	2	nmr	nmr	NOUN
eurjchem-788	44	3	(	(	PUNCT
eurjchem-788	44	4	75	75	NUM
eurjchem-788	44	5	mhz	mhz	NOUN
eurjchem-788	44	6	,	,	PUNCT
eurjchem-788	44	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	44	8	+	+	CCONJ
eurjchem-788	44	9	cdcl3	cdcl3	PROPN
eurjchem-788	44	10	,	,	PUNCT
eurjchem-788	44	11	δ	δ	PROPN
eurjchem-788	44	12	,	,	PUNCT
eurjchem-788	44	13	ppm	ppm	NOUN
eurjchem-788	44	14	):	):	PUNCT
eurjchem-788	44	15	165.2	165.2	NUM
eurjchem-788	44	16	(	(	PUNCT
eurjchem-788	44	17	1c	1c	NOUN
eurjchem-788	44	18	,	,	PUNCT
eurjchem-788	44	19	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	44	20	)	)	PUNCT
eurjchem-788	44	21	,	,	PUNCT
eurjchem-788	44	22	137.6	137.6	NUM
eurjchem-788	44	23	(	(	PUNCT
eurjchem-788	44	24	1c	1c	NOUN
eurjchem-788	44	25	,	,	PUNCT
eurjchem-788	44	26	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	44	27	)	)	PUNCT
eurjchem-788	44	28	,	,	PUNCT
eurjchem-788	44	29	134.7	134.7	NUM
eurjchem-788	44	30	(	(	PUNCT
eurjchem-788	44	31	1c	1c	NOUN
eurjchem-788	44	32	,	,	PUNCT
eurjchem-788	44	33	ar‐c	ar‐c	PROPN
eurjchem-788	44	34	)	)	PUNCT
eurjchem-788	44	35	,	,	PUNCT
eurjchem-788	44	36	132.1	132.1	NUM
eurjchem-788	44	37	(	(	PUNCT
eurjchem-788	44	38	1c	1c	NOUN
eurjchem-788	44	39	,	,	PUNCT
eurjchem-788	44	40	ar‐c	ar‐c	PROPN
eurjchem-788	44	41	)	)	PUNCT
eurjchem-788	44	42	,	,	PUNCT
eurjchem-788	44	43	128.1	128.1	NUM
eurjchem-788	44	44	(	(	PUNCT
eurjchem-788	44	45	2c	2c	NUM
eurjchem-788	44	46	,	,	PUNCT
eurjchem-788	44	47	ar‐c	ar‐c	PROPN
eurjchem-788	44	48	)	)	PUNCT
eurjchem-788	44	49	,	,	PUNCT
eurjchem-788	44	50	127.8	127.8	NUM
eurjchem-788	44	51	(	(	PUNCT
eurjchem-788	44	52	2c	2c	NUM
eurjchem-788	44	53	,	,	PUNCT
eurjchem-788	44	54	ar‐c	ar‐c	PROPN
eurjchem-788	44	55	)	)	PUNCT
eurjchem-788	44	56	,	,	PUNCT
eurjchem-788	44	57	121.2	121.2	NUM
eurjchem-788	44	58	(	(	PUNCT
eurjchem-788	44	59	1c	1c	NOUN
eurjchem-788	44	60	,	,	PUNCT
eurjchem-788	44	61	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	44	62	)	)	PUNCT
eurjchem-788	44	63	,	,	PUNCT
eurjchem-788	44	64	115.6	115.6	NUM
eurjchem-788	44	65	(	(	PUNCT
eurjchem-788	44	66	1c	1c	NOUN
eurjchem-788	44	67	,	,	PUNCT
eurjchem-788	44	68	cn	cn	PROPN
eurjchem-788	44	69	)	)	PUNCT
eurjchem-788	44	70	,	,	PUNCT
eurjchem-788	44	71	104.0	104.0	NUM
eurjchem-788	44	72	(	(	PUNCT
eurjchem-788	44	73	1c	1c	NOUN
eurjchem-788	44	74	,	,	PUNCT
eurjchem-788	44	75	thienyl‐c	thienyl‐c	NOUN
eurjchem-788	44	76	)	)	PUNCT
eurjchem-788	44	77	.	.	PUNCT
eurjchem-788	45	1	2.2.2	2.2.2	X
eurjchem-788	45	2	.	.	PUNCT
eurjchem-788	45	3	general	general	ADJ
eurjchem-788	45	4	method	method	NOUN
eurjchem-788	45	5	for	for	ADP
eurjchem-788	45	6	the	the	DET
eurjchem-788	45	7	friedländer	friedländer	PROPN
eurjchem-788	45	8	reaction	reaction	PROPN
eurjchem-788	45	9	2.2.2.1	2.2.2.1	PROPN
eurjchem-788	45	10	.	.	PUNCT
eurjchem-788	46	1	preparation	preparation	NOUN
eurjchem-788	46	2	of	of	ADP
eurjchem-788	46	3	the	the	DET
eurjchem-788	46	4	activated	activated	ADJ
eurjchem-788	46	5	bentonite	bentonite	NOUN
eurjchem-788	46	6	in	in	ADP
eurjchem-788	46	7	a	a	DET
eurjchem-788	46	8	reactor	reactor	NOUN
eurjchem-788	46	9	equipped	equip	VERB
eurjchem-788	46	10	with	with	ADP
eurjchem-788	46	11	a	a	DET
eurjchem-788	46	12	condenser	condenser	NOUN
eurjchem-788	46	13	,	,	PUNCT
eurjchem-788	46	14	a	a	DET
eurjchem-788	46	15	stirrer	stirrer	ADJ
eurjchem-788	46	16	magnetic	magnetic	NOUN
eurjchem-788	46	17	and	and	CCONJ
eurjchem-788	46	18	a	a	DET
eurjchem-788	46	19	thermometer	thermometer	NOUN
eurjchem-788	46	20	was	be	AUX
eurjchem-788	46	21	charged	charge	VERB
eurjchem-788	46	22	a	a	DET
eurjchem-788	46	23	dry	dry	ADJ
eurjchem-788	46	24	bentonite	bentonite	NOUN
eurjchem-788	46	25	and	and	CCONJ
eurjchem-788	46	26	then	then	ADV
eurjchem-788	46	27	concentrated	concentrated	ADJ
eurjchem-788	46	28	sulfuric	sulfuric	NOUN
eurjchem-788	46	29	acid	acid	NOUN
eurjchem-788	46	30	was	be	AUX
eurjchem-788	46	31	added	add	VERB
eurjchem-788	46	32	(	(	PUNCT
eurjchem-788	46	33	mass	mass	NOUN
eurjchem-788	46	34	of	of	ADP
eurjchem-788	46	35	h2so4	h2so4	PROPN
eurjchem-788	46	36	/	/	SYM
eurjchem-788	46	37	mass	mass	PROPN
eurjchem-788	46	38	of	of	ADP
eurjchem-788	46	39	bentonite	bentonite	NOUN
eurjchem-788	46	40	=	=	PUNCT
eurjchem-788	46	41	0.3	0.3	NUM
eurjchem-788	46	42	)	)	PUNCT
eurjchem-788	46	43	.	.	PUNCT
eurjchem-788	47	1	the	the	DET
eurjchem-788	47	2	mixture	mixture	NOUN
eurjchem-788	47	3	was	be	AUX
eurjchem-788	47	4	then	then	ADV
eurjchem-788	47	5	heated	heat	VERB
eurjchem-788	47	6	at	at	ADP
eurjchem-788	47	7	about	about	ADV
eurjchem-788	47	8	100	100	NUM
eurjchem-788	47	9	°	°	NOUN
eurjchem-788	47	10	c	c	NOUN
eurjchem-788	47	11	,	,	PUNCT
eurjchem-788	47	12	the	the	DET
eurjchem-788	47	13	temperature	temperature	NOUN
eurjchem-788	47	14	is	be	AUX
eurjchem-788	47	15	kept	keep	VERB
eurjchem-788	47	16	constant	constant	ADJ
eurjchem-788	47	17	during	during	ADP
eurjchem-788	47	18	the	the	DET
eurjchem-788	47	19	entire	entire	ADJ
eurjchem-788	47	20	process	process	NOUN
eurjchem-788	47	21	activation	activation	NOUN
eurjchem-788	47	22	,	,	PUNCT
eurjchem-788	47	23	by	by	ADP
eurjchem-788	47	24	means	mean	NOUN
eurjchem-788	47	25	of	of	ADP
eurjchem-788	47	26	a	a	DET
eurjchem-788	47	27	water	water	NOUN
eurjchem-788	47	28	bath	bath	NOUN
eurjchem-788	47	29	.	.	PUNCT
eurjchem-788	48	1	the	the	DET
eurjchem-788	48	2	contact	contact	NOUN
eurjchem-788	48	3	time	time	NOUN
eurjchem-788	48	4	is	be	AUX
eurjchem-788	48	5	determined	determine	VERB
eurjchem-788	48	6	from	from	ADP
eurjchem-788	48	7	the	the	DET
eurjchem-788	48	8	moment	moment	NOUN
eurjchem-788	48	9	when	when	SCONJ
eurjchem-788	48	10	the	the	DET
eurjchem-788	48	11	temperature	temperature	NOUN
eurjchem-788	48	12	of	of	ADP
eurjchem-788	48	13	the	the	DET
eurjchem-788	48	14	suspension	suspension	NOUN
eurjchem-788	48	15	reaches	reach	VERB
eurjchem-788	48	16	100	100	NUM
eurjchem-788	48	17	°	°	NOUN
eurjchem-788	48	18	c	c	X
eurjchem-788	48	19	.	.	PUNCT
eurjchem-788	49	1	activated	activate	VERB
eurjchem-788	49	2	bentonite	bentonite	NOUN
eurjchem-788	49	3	is	be	AUX
eurjchem-788	49	4	then	then	ADV
eurjchem-788	49	5	filtered	filter	VERB
eurjchem-788	49	6	and	and	CCONJ
eurjchem-788	49	7	then	then	ADV
eurjchem-788	49	8	washed	wash	VERB
eurjchem-788	49	9	with	with	ADP
eurjchem-788	49	10	distilled	distil	VERB
eurjchem-788	49	11	water	water	NOUN
eurjchem-788	49	12	until	until	SCONJ
eurjchem-788	49	13	all	all	DET
eurjchem-788	49	14	traces	trace	NOUN
eurjchem-788	49	15	acid	acid	ADJ
eurjchem-788	49	16	.	.	PUNCT
eurjchem-788	50	1	the	the	DET
eurjchem-788	50	2	wash	wash	NOUN
eurjchem-788	50	3	cycle	cycle	NOUN
eurjchem-788	50	4	is	be	AUX
eurjchem-788	50	5	completed	complete	VERB
eurjchem-788	50	6	when	when	SCONJ
eurjchem-788	50	7	the	the	DET
eurjchem-788	50	8	filtrate	filtrate	NOUN
eurjchem-788	50	9	no	no	ADV
eurjchem-788	50	10	longer	long	ADV
eurjchem-788	50	11	gives	give	VERB
eurjchem-788	50	12	the	the	DET
eurjchem-788	50	13	reaction	reaction	NOUN
eurjchem-788	50	14	of	of	ADP
eurjchem-788	50	15	sulphates	sulphate	NOUN
eurjchem-788	50	16	with	with	ADP
eurjchem-788	50	17	barium	barium	NOUN
eurjchem-788	50	18	chloride	chloride	NOUN
eurjchem-788	50	19	.	.	PUNCT
eurjchem-788	51	1	bentonite	bentonite	NOUN
eurjchem-788	51	2	,	,	PUNCT
eurjchem-788	51	3	free	free	ADJ
eurjchem-788	51	4	of	of	ADP
eurjchem-788	51	5	sulphates	sulphate	NOUN
eurjchem-788	51	6	ions	ion	NOUN
eurjchem-788	51	7	is	be	AUX
eurjchem-788	51	8	then	then	ADV
eurjchem-788	51	9	dried	dry	VERB
eurjchem-788	51	10	at	at	ADP
eurjchem-788	51	11	105	105	NUM
eurjchem-788	51	12	to	to	PART
eurjchem-788	51	13	110	110	NUM
eurjchem-788	51	14	°	°	NOUN
eurjchem-788	51	15	c	c	NOUN
eurjchem-788	51	16	,	,	PUNCT
eurjchem-788	51	17	then	then	ADV
eurjchem-788	51	18	ground	ground	NOUN
eurjchem-788	51	19	and	and	CCONJ
eurjchem-788	51	20	sieved	sieve	VERB
eurjchem-788	51	21	.	.	PUNCT
eurjchem-788	52	1	2.2.2.2	2.2.2.2	X
eurjchem-788	52	2	.	.	NOUN
eurjchem-788	52	3	procedure	procedure	NOUN
eurjchem-788	52	4	for	for	ADP
eurjchem-788	52	5	the	the	DET
eurjchem-788	52	6	synthesis	synthesis	NOUN
eurjchem-788	52	7	of	of	ADP
eurjchem-788	52	8	compounds	compound	NOUN
eurjchem-788	52	9	2	2	NUM
eurjchem-788	52	10	and	and	CCONJ
eurjchem-788	52	11	3	3	NUM
eurjchem-788	52	12	to	to	ADP
eurjchem-788	52	13	a	a	DET
eurjchem-788	52	14	suspension	suspension	NOUN
eurjchem-788	52	15	of	of	ADP
eurjchem-788	52	16	catalyst	catalyst	NOUN
eurjchem-788	52	17	(	(	PUNCT
eurjchem-788	52	18	alcl3	alcl3	NOUN
eurjchem-788	52	19	or	or	CCONJ
eurjchem-788	52	20	activated	activate	VERB
eurjchem-788	52	21	bentonite	bentonite	NOUN
eurjchem-788	52	22	)	)	PUNCT
eurjchem-788	52	23	in	in	ADP
eurjchem-788	52	24	dry	dry	ADJ
eurjchem-788	52	25	1,2‐dichloroethane	1,2‐dichloroethane	NUM
eurjchem-788	52	26	at	at	ADP
eurjchem-788	52	27	room	room	NOUN
eurjchem-788	52	28	temperature	temperature	NOUN
eurjchem-788	52	29	under	under	ADP
eurjchem-788	52	30	nitrogen	nitrogen	NOUN
eurjchem-788	52	31	,	,	PUNCT
eurjchem-788	52	32	the	the	DET
eurjchem-788	52	33	corresponding	corresponding	ADJ
eurjchem-788	52	34	aminothiophene	aminothiophene	NOUN
eurjchem-788	52	35	1	1	NUM
eurjchem-788	52	36	(	(	PUNCT
eurjchem-788	52	37	5	5	NUM
eurjchem-788	52	38	mmol	mmol	NOUN
eurjchem-788	52	39	)	)	PUNCT
eurjchem-788	52	40	and	and	CCONJ
eurjchem-788	52	41	ketone	ketone	NOUN
eurjchem-788	52	42	(	(	PUNCT
eurjchem-788	52	43	10	10	NUM
eurjchem-788	52	44	mmol	mmol	NOUN
eurjchem-788	52	45	)	)	PUNCT
eurjchem-788	52	46	were	be	AUX
eurjchem-788	52	47	added	add	VERB
eurjchem-788	52	48	.	.	PUNCT
eurjchem-788	53	1	the	the	DET
eurjchem-788	53	2	mixture	mixture	NOUN
eurjchem-788	53	3	was	be	AUX
eurjchem-788	53	4	refluxed	refluxe	VERB
eurjchem-788	53	5	until	until	SCONJ
eurjchem-788	53	6	the	the	DET
eurjchem-788	53	7	reaction	reaction	NOUN
eurjchem-788	53	8	was	be	AUX
eurjchem-788	53	9	complete	complete	ADJ
eurjchem-788	53	10	(	(	PUNCT
eurjchem-788	53	11	monitoring	monitoring	NOUN
eurjchem-788	53	12	by	by	ADP
eurjchem-788	53	13	tlc	tlc	NOUN
eurjchem-788	53	14	)	)	PUNCT
eurjchem-788	53	15	.	.	PUNCT
eurjchem-788	54	1	when	when	SCONJ
eurjchem-788	54	2	alcl3	alcl3	PROPN
eurjchem-788	54	3	was	be	AUX
eurjchem-788	54	4	used	use	VERB
eurjchem-788	54	5	:	:	PUNCT
eurjchem-788	54	6	a	a	DET
eurjchem-788	54	7	solution	solution	NOUN
eurjchem-788	54	8	of	of	ADP
eurjchem-788	54	9	naoh	naoh	NOUN
eurjchem-788	54	10	(	(	PUNCT
eurjchem-788	54	11	10	10	NUM
eurjchem-788	54	12	%	%	NOUN
eurjchem-788	54	13	)	)	PUNCT
eurjchem-788	54	14	was	be	AUX
eurjchem-788	54	15	added	add	VERB
eurjchem-788	54	16	until	until	ADP
eurjchem-788	54	17	ph	ph	NOUN
eurjchem-788	54	18	=	=	SYM
eurjchem-788	54	19	9	9	NUM
eurjchem-788	54	20	and	and	CCONJ
eurjchem-788	54	21	then	then	ADV
eurjchem-788	54	22	,	,	PUNCT
eurjchem-788	54	23	a	a	DET
eurjchem-788	54	24	mixture	mixture	NOUN
eurjchem-788	54	25	of	of	ADP
eurjchem-788	54	26	water	water	NOUN
eurjchem-788	54	27	:	:	PUNCT
eurjchem-788	54	28	thf	thf	NOUN
eurjchem-788	54	29	(	(	PUNCT
eurjchem-788	54	30	v	v	NOUN
eurjchem-788	54	31	:	:	PUNCT
eurjchem-788	54	32	v	v	NOUN
eurjchem-788	54	33	,	,	PUNCT
eurjchem-788	54	34	1:2	1:2	NUM
eurjchem-788	54	35	)	)	PUNCT
eurjchem-788	54	36	was	be	AUX
eurjchem-788	54	37	added	add	VERB
eurjchem-788	54	38	and	and	CCONJ
eurjchem-788	54	39	the	the	DET
eurjchem-788	54	40	mixture	mixture	NOUN
eurjchem-788	54	41	was	be	AUX
eurjchem-788	54	42	extracted	extract	VERB
eurjchem-788	54	43	with	with	ADP
eurjchem-788	54	44	dichloromethane	dichloromethane	NOUN
eurjchem-788	54	45	.	.	PUNCT
eurjchem-788	55	1	the	the	DET
eurjchem-788	55	2	organic	organic	ADJ
eurjchem-788	55	3	layer	layer	NOUN
eurjchem-788	55	4	was	be	AUX
eurjchem-788	55	5	dried	dry	VERB
eurjchem-788	55	6	,	,	PUNCT
eurjchem-788	55	7	filtered	filter	VERB
eurjchem-788	55	8	and	and	CCONJ
eurjchem-788	55	9	evaporated	evaporate	VERB
eurjchem-788	55	10	.	.	PUNCT
eurjchem-788	56	1	the	the	DET
eurjchem-788	56	2	collected	collect	VERB
eurjchem-788	56	3	solid	solid	NOUN
eurjchem-788	56	4	was	be	AUX
eurjchem-788	56	5	submitted	submit	VERB
eurjchem-788	56	6	to	to	ADP
eurjchem-788	56	7	chromatography	chromatography	NOUN
eurjchem-788	56	8	(	(	PUNCT
eurjchem-788	56	9	ch2cl2	ch2cl2	NOUN
eurjchem-788	56	10	:	:	PUNCT
eurjchem-788	56	11	meoh	meoh	PROPN
eurjchem-788	56	12	,	,	PUNCT
eurjchem-788	56	13	9:1	9:1	NUM
eurjchem-788	56	14	,	,	PUNCT
eurjchem-788	56	15	v	v	NOUN
eurjchem-788	56	16	:	:	SYM
eurjchem-788	56	17	v	v	NOUN
eurjchem-788	56	18	)	)	PUNCT
eurjchem-788	56	19	to	to	PART
eurjchem-788	56	20	give	give	VERB
eurjchem-788	56	21	the	the	DET
eurjchem-788	56	22	desired	desire	VERB
eurjchem-788	56	23	compound	compound	NOUN
eurjchem-788	56	24	.	.	PUNCT
eurjchem-788	57	1	when	when	SCONJ
eurjchem-788	57	2	activated	activate	VERB
eurjchem-788	57	3	bentonite	bentonite	NOUN
eurjchem-788	57	4	was	be	AUX
eurjchem-788	57	5	used	use	VERB
eurjchem-788	57	6	as	as	ADP
eurjchem-788	57	7	support	support	NOUN
eurjchem-788	57	8	catalyst	catalyst	NOUN
eurjchem-788	57	9	:	:	PUNCT
eurjchem-788	57	10	the	the	DET
eurjchem-788	57	11	mixture	mixture	NOUN
eurjchem-788	57	12	was	be	AUX
eurjchem-788	57	13	filtered	filter	VERB
eurjchem-788	57	14	,	,	PUNCT
eurjchem-788	57	15	a	a	DET
eurjchem-788	57	16	solution	solution	NOUN
eurjchem-788	57	17	of	of	ADP
eurjchem-788	57	18	water	water	NOUN
eurjchem-788	57	19	:	:	PUNCT
eurjchem-788	57	20	thf	thf	NOUN
eurjchem-788	57	21	(	(	PUNCT
eurjchem-788	57	22	1:2	1:2	NUM
eurjchem-788	57	23	,	,	PUNCT
eurjchem-788	57	24	v	v	NOUN
eurjchem-788	57	25	:	:	SYM
eurjchem-788	57	26	v	v	NOUN
eurjchem-788	57	27	)	)	PUNCT
eurjchem-788	57	28	was	be	AUX
eurjchem-788	57	29	added	add	VERB
eurjchem-788	57	30	and	and	CCONJ
eurjchem-788	57	31	usually	usually	ADV
eurjchem-788	57	32	work‐up	work‐up	INTJ
eurjchem-788	57	33	provided	provide	VERB
eurjchem-788	57	34	the	the	DET
eurjchem-788	57	35	product	product	NOUN
eurjchem-788	57	36	(	(	PUNCT
eurjchem-788	57	37	scheme	scheme	NOUN
eurjchem-788	57	38	2	2	NUM
eurjchem-788	57	39	)	)	PUNCT
eurjchem-788	57	40	.	.	PUNCT
eurjchem-788	58	1	11‐amino‐2,3,4,7,8,9‐hexahydro[1]benzothieno[2,3‐b	11‐amino‐2,3,4,7,8,9‐hexahydro[1]benzothieno[2,3‐b	NUM
eurjchem-788	58	2	]	]	X
eurjchem-788	58	3	quinolin‐10(1h)‐one	quinolin‐10(1h)‐one	PROPN
eurjchem-788	58	4	(	(	PUNCT
eurjchem-788	58	5	2a	2a	NUM
eurjchem-788	58	6	):	):	PUNCT
eurjchem-788	58	7	following	follow	VERB
eurjchem-788	58	8	the	the	DET
eurjchem-788	58	9	general	general	ADJ
eurjchem-788	58	10	method	method	NOUN
eurjchem-788	58	11	for	for	ADP
eurjchem-788	58	12	the	the	DET
eurjchem-788	58	13	friedländer	friedländer	NOUN
eurjchem-788	58	14	reaction	reaction	NOUN
eurjchem-788	58	15	,	,	PUNCT
eurjchem-788	58	16	alcl3	alcl3	PROPN
eurjchem-788	58	17	(	(	PUNCT
eurjchem-788	58	18	800	800	NUM
eurjchem-788	58	19	mg	mg	NUM
eurjchem-788	58	20	)	)	PUNCT
eurjchem-788	58	21	or	or	CCONJ
eurjchem-788	58	22	activated	activate	VERB
eurjchem-788	58	23	bentonite	bentonite	NOUN
eurjchem-788	58	24	(	(	PUNCT
eurjchem-788	58	25	1000	1000	NUM
eurjchem-788	58	26	mg	mg	NOUN
eurjchem-788	58	27	)	)	PUNCT
eurjchem-788	58	28	in	in	ADP
eurjchem-788	58	29	dry	dry	ADJ
eurjchem-788	58	30	1,2‐dichloroethane	1,2‐dichloroethane	NOUN
eurjchem-788	58	31	(	(	PUNCT
eurjchem-788	58	32	50	50	NUM
eurjchem-788	58	33	ml	ml	NOUN
eurjchem-788	58	34	)	)	PUNCT
eurjchem-788	58	35	was	be	AUX
eurjchem-788	58	36	reacted	react	VERB
eurjchem-788	58	37	with	with	ADP
eurjchem-788	58	38	cyclohexane‐1,3‐dione	cyclohexane‐1,3‐dione	PROPN
eurjchem-788	58	39	(	(	PUNCT
eurjchem-788	58	40	10	10	NUM
eurjchem-788	58	41	mmol	mmol	NOUN
eurjchem-788	58	42	)	)	PUNCT
eurjchem-788	58	43	and	and	CCONJ
eurjchem-788	58	44	aminothiophene	aminothiophene	VERB
eurjchem-788	58	45	1a	1a	PROPN
eurjchem-788	58	46	(	(	PUNCT
eurjchem-788	58	47	5	5	NUM
eurjchem-788	58	48	mmol	mmol	NOUN
eurjchem-788	58	49	)	)	PUNCT
eurjchem-788	58	50	.	.	PUNCT
eurjchem-788	59	1	the	the	DET
eurjchem-788	59	2	mixture	mixture	NOUN
eurjchem-788	59	3	was	be	AUX
eurjchem-788	59	4	refluxed	refluxe	VERB
eurjchem-788	59	5	for	for	ADP
eurjchem-788	59	6	24	24	NUM
eurjchem-788	59	7	h.	h.	PROPN
eurjchem-788	59	8	work‐up	work‐up	PROPN
eurjchem-788	59	9	and	and	CCONJ
eurjchem-788	59	10	chromatography	chromatography	NOUN
eurjchem-788	59	11	provided	provide	VERB
eurjchem-788	59	12	compound	compound	NOUN
eurjchem-788	59	13	2a	2a	NUM
eurjchem-788	59	14	.	.	PUNCT
eurjchem-788	60	1	color	color	NOUN
eurjchem-788	60	2	:	:	PUNCT
eurjchem-788	60	3	brown	brown	ADJ
eurjchem-788	60	4	.	.	PUNCT
eurjchem-788	61	1	yield	yield	NOUN
eurjchem-788	61	2	:	:	PUNCT
eurjchem-788	61	3	67	67	NUM
eurjchem-788	61	4	%	%	NOUN
eurjchem-788	61	5	.	.	PUNCT
eurjchem-788	62	1	m.p	m.p	PROPN
eurjchem-788	62	2	.	.	PROPN
eurjchem-788	62	3	:	:	PUNCT
eurjchem-788	63	1	219‐221	219‐221	NUM
eurjchem-788	63	2	°	°	ADP
eurjchem-788	63	3	c	c	NOUN
eurjchem-788	63	4	.	.	PUNCT
eurjchem-788	64	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	64	2	(	(	PUNCT
eurjchem-788	64	3	kbr	kbr	PROPN
eurjchem-788	64	4	,	,	PUNCT
eurjchem-788	64	5	ν	ν	PROPN
eurjchem-788	64	6	,	,	PUNCT
eurjchem-788	64	7	cm‐1	cm‐1	PROPN
eurjchem-788	64	8	):	):	PUNCT
eurjchem-788	64	9	3382	3382	NUM
eurjchem-788	64	10	,	,	PUNCT
eurjchem-788	64	11	3215	3215	NUM
eurjchem-788	64	12	(nh	(nh	NOUN
eurjchem-788	64	13	)	)	PUNCT
eurjchem-788	64	14	(	(	PUNCT
eurjchem-788	64	15	nh2	nh2	PROPN
eurjchem-788	64	16	)	)	PUNCT
eurjchem-788	64	17	,	,	PUNCT
eurjchem-788	64	18	1638	1638	NUM
eurjchem-788	64	19	(co	(co	NOUN
eurjchem-788	64	20	)	)	PUNCT
eurjchem-788	64	21	,	,	PUNCT
eurjchem-788	64	22	1589	1589	NUM
eurjchem-788	64	23	(nh	(nh	NOUN
eurjchem-788	64	24	)	)	PUNCT
eurjchem-788	64	25	(	(	PUNCT
eurjchem-788	64	26	nh2	nh2	PROPN
eurjchem-788	64	27	)	)	PUNCT
eurjchem-788	64	28	,	,	PUNCT
eurjchem-788	64	29	1328	1328	NUM
eurjchem-788	64	30	(	(	PUNCT
eurjchem-788	64	31	nh2	nh2	PROPN
eurjchem-788	64	32	)	)	PUNCT
eurjchem-788	64	33	.	.	PUNCT
eurjchem-788	65	1	1h	1h	NUM
eurjchem-788	65	2	nmr	nmr	NOUN
eurjchem-788	65	3	(	(	PUNCT
eurjchem-788	65	4	300	300	NUM
eurjchem-788	65	5	mhz	mhz	NOUN
eurjchem-788	65	6	,	,	PUNCT
eurjchem-788	65	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	65	8	,	,	PUNCT
eurjchem-788	65	9	δ	δ	PROPN
eurjchem-788	65	10	,	,	PUNCT
eurjchem-788	65	11	ppm	ppm	NUM
eurjchem-788	65	12	):	):	PUNCT
eurjchem-788	65	13	5.08	5.08	NUM
eurjchem-788	65	14	(	(	PUNCT
eurjchem-788	65	15	s	s	PROPN
eurjchem-788	65	16	,	,	PUNCT
eurjchem-788	65	17	br	br	PROPN
eurjchem-788	65	18	,	,	PUNCT
eurjchem-788	65	19	1h	1h	NUM
eurjchem-788	65	20	,	,	PUNCT
eurjchem-788	65	21	nh2	nh2	PROPN
eurjchem-788	65	22	)	)	PUNCT
eurjchem-788	65	23	,	,	PUNCT
eurjchem-788	65	24	3.1‐2.8	3.1‐2.8	NUM
eurjchem-788	65	25	(	(	PUNCT
eurjchem-788	65	26	m	m	PROPN
eurjchem-788	65	27	,	,	PUNCT
eurjchem-788	65	28	4h	4h	NOUN
eurjchem-788	65	29	,	,	PUNCT
eurjchem-788	65	30	2*ch2	2*ch2	NUM
eurjchem-788	65	31	)	)	PUNCT
eurjchem-788	65	32	,	,	PUNCT
eurjchem-788	65	33	2.66	2.66	NUM
eurjchem-788	65	34	(	(	PUNCT
eurjchem-788	65	35	m	m	PROPN
eurjchem-788	65	36	,	,	PUNCT
eurjchem-788	65	37	2h	2h	NUM
eurjchem-788	65	38	,	,	PUNCT
eurjchem-788	65	39	‐ch2‐co‐	‐ch2‐co‐	NOUN
eurjchem-788	65	40	)	)	PUNCT
eurjchem-788	65	41	,	,	PUNCT
eurjchem-788	65	42	2.53	2.53	NUM
eurjchem-788	65	43	(	(	PUNCT
eurjchem-788	65	44	m	m	PROPN
eurjchem-788	65	45	,	,	PUNCT
eurjchem-788	65	46	2h	2h	NUM
eurjchem-788	65	47	,	,	PUNCT
eurjchem-788	65	48	=	=	NOUN
eurjchem-788	65	49	c‐ch2	c‐ch2	PROPN
eurjchem-788	65	50	)	)	PUNCT
eurjchem-788	65	51	,	,	PUNCT
eurjchem-788	65	52	2.12	2.12	NUM
eurjchem-788	65	53	(	(	PUNCT
eurjchem-788	65	54	m	m	PROPN
eurjchem-788	65	55	,	,	PUNCT
eurjchem-788	65	56	2h	2h	NUM
eurjchem-788	65	57	,	,	PUNCT
eurjchem-788	65	58	‐ch2‐ch2‐ch2‐co‐	‐ch2‐ch2‐ch2‐co‐	PROPN
eurjchem-788	65	59	)	)	PUNCT
eurjchem-788	65	60	,	,	PUNCT
eurjchem-788	65	61	1.74	1.74	NUM
eurjchem-788	65	62	(	(	PUNCT
eurjchem-788	65	63	m	m	PROPN
eurjchem-788	65	64	,	,	PUNCT
eurjchem-788	65	65	4h	4h	NOUN
eurjchem-788	65	66	,	,	PUNCT
eurjchem-788	65	67	2*ch2	2*ch2	NUM
eurjchem-788	65	68	)	)	PUNCT
eurjchem-788	65	69	,	,	PUNCT
eurjchem-788	65	70	1.33	1.33	NUM
eurjchem-788	65	71	(	(	PUNCT
eurjchem-788	65	72	s	s	PROPN
eurjchem-788	65	73	,	,	PUNCT
eurjchem-788	65	74	br	br	PROPN
eurjchem-788	65	75	,	,	PUNCT
eurjchem-788	65	76	1h	1h	NUM
eurjchem-788	65	77	,	,	PUNCT
eurjchem-788	65	78	nh2	nh2	PROPN
eurjchem-788	65	79	linked	link	VERB
eurjchem-788	65	80	h‐bonding	h‐bonde	VERB
eurjchem-788	65	81	to	to	PART
eurjchem-788	65	82	co	co	VERB
eurjchem-788	65	83	)	)	PUNCT
eurjchem-788	65	84	.	.	PUNCT
eurjchem-788	66	1	13c	13c	NOUN
eurjchem-788	66	2	nmr	nmr	NOUN
eurjchem-788	66	3	(	(	PUNCT
eurjchem-788	66	4	75	75	NUM
eurjchem-788	66	5	mhz	mhz	NOUN
eurjchem-788	66	6	,	,	PUNCT
eurjchem-788	66	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	66	8	,	,	PUNCT
eurjchem-788	66	9	δ	δ	PROPN
eurjchem-788	66	10	,	,	PUNCT
eurjchem-788	66	11	ppm	ppm	NUM
eurjchem-788	66	12	):	):	PUNCT
eurjchem-788	66	13	199.7	199.7	NUM
eurjchem-788	66	14	(	(	PUNCT
eurjchem-788	66	15	1c	1c	NOUN
eurjchem-788	66	16	,	,	PUNCT
eurjchem-788	66	17	co	co	NOUN
eurjchem-788	66	18	)	)	PUNCT
eurjchem-788	66	19	,	,	PUNCT
eurjchem-788	66	20	162.9	162.9	NUM
eurjchem-788	66	21	(	(	PUNCT
eurjchem-788	66	22	1c	1c	NOUN
eurjchem-788	66	23	,	,	PUNCT
eurjchem-788	66	24	‐s‐c	‐s‐c	ADJ
eurjchem-788	66	25	=	=	SYM
eurjchem-788	66	26	c(n)‐	c(n)‐	NOUN
eurjchem-788	66	27	)	)	PUNCT
eurjchem-788	66	28	,	,	PUNCT
eurjchem-788	66	29	161.8	161.8	NUM
eurjchem-788	66	30	(	(	PUNCT
eurjchem-788	66	31	1c	1c	NOUN
eurjchem-788	66	32	,	,	PUNCT
eurjchem-788	66	33	‐n	‐n	ADJ
eurjchem-788	66	34	=	=	NOUN
eurjchem-788	66	35	c‐	c‐	NOUN
eurjchem-788	66	36	ch2‐	ch2‐	NOUN
eurjchem-788	66	37	)	)	PUNCT
eurjchem-788	66	38	,	,	PUNCT
eurjchem-788	66	39	153.1	153.1	NUM
eurjchem-788	66	40	(	(	PUNCT
eurjchem-788	66	41	1c	1c	NOUN
eurjchem-788	66	42	,	,	PUNCT
eurjchem-788	66	43	=	=	NOUN
eurjchem-788	66	44	c‐nh2	c‐nh2	PROPN
eurjchem-788	66	45	)	)	PUNCT
eurjchem-788	66	46	,	,	PUNCT
eurjchem-788	66	47	132.7	132.7	NUM
eurjchem-788	66	48	(	(	PUNCT
eurjchem-788	66	49	1c	1c	NOUN
eurjchem-788	66	50	,	,	PUNCT
eurjchem-788	66	51	‐c	‐c	NOUN
eurjchem-788	66	52	=	=	NOUN
eurjchem-788	66	53	c‐s	c‐s	NOUN
eurjchem-788	66	54	)	)	PUNCT
eurjchem-788	66	55	,	,	PUNCT
eurjchem-788	66	56	128.6	128.6	NUM
eurjchem-788	66	57	(	(	PUNCT
eurjchem-788	66	58	1c	1c	NOUN
eurjchem-788	66	59	,	,	PUNCT
eurjchem-788	66	60	‐c	‐c	NOUN
eurjchem-788	66	61	=	=	NOUN
eurjchem-788	66	62	c‐	c‐	NOUN
eurjchem-788	66	63	s	s	PART
eurjchem-788	66	64	)	)	PUNCT
eurjchem-788	66	65	,	,	PUNCT
eurjchem-788	66	66	118.2	118.2	NUM
eurjchem-788	66	67	(	(	PUNCT
eurjchem-788	66	68	1c	1c	NOUN
eurjchem-788	66	69	,	,	PUNCT
eurjchem-788	66	70	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	66	71	=	=	NOUN
eurjchem-788	66	72	c‐c‐nh2	c‐c‐nh2	PROPN
eurjchem-788	66	73	)	)	PUNCT
eurjchem-788	66	74	,	,	PUNCT
eurjchem-788	66	75	112.3	112.3	NUM
eurjchem-788	66	76	(	(	PUNCT
eurjchem-788	66	77	1c	1c	NOUN
eurjchem-788	66	78	,	,	PUNCT
eurjchem-788	66	79	pyridinyl‐c‐co	pyridinyl‐c‐co	PRON
eurjchem-788	66	80	)	)	PUNCT
eurjchem-788	66	81	,	,	PUNCT
eurjchem-788	66	82	40.1	40.1	NUM
eurjchem-788	66	83	(	(	PUNCT
eurjchem-788	66	84	1c	1c	NOUN
eurjchem-788	66	85	,	,	PUNCT
eurjchem-788	66	86	‐ch2‐co	‐ch2‐co	NOUN
eurjchem-788	66	87	)	)	PUNCT
eurjchem-788	66	88	,	,	PUNCT
eurjchem-788	66	89	30.8	30.8	NUM
eurjchem-788	66	90	(	(	PUNCT
eurjchem-788	66	91	1c	1c	NOUN
eurjchem-788	66	92	,	,	PUNCT
eurjchem-788	66	93	‐ch2‐ch2‐co	‐ch2‐ch2‐co	NOUN
eurjchem-788	66	94	)	)	PUNCT
eurjchem-788	66	95	,	,	PUNCT
eurjchem-788	66	96	28.4	28.4	NUM
eurjchem-788	66	97	(	(	PUNCT
eurjchem-788	66	98	1c	1c	X
eurjchem-788	66	99	,	,	PUNCT
eurjchem-788	66	100	thienyl‐	thienyl‐	NOUN
eurjchem-788	66	101	ch2‐ch2‐ch2‐ch2‐	ch2‐ch2‐ch2‐ch2‐	PROPN
eurjchem-788	66	102	)	)	PUNCT
eurjchem-788	66	103	,	,	PUNCT
eurjchem-788	66	104	26.9	26.9	NUM
eurjchem-788	66	105	(	(	PUNCT
eurjchem-788	66	106	1c	1c	NOUN
eurjchem-788	66	107	,	,	PUNCT
eurjchem-788	66	108	thienyl‐ch2‐ch2‐ch2‐ch2‐	thienyl‐ch2‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	66	109	)	)	PUNCT
eurjchem-788	66	110	,	,	PUNCT
eurjchem-788	66	111	22.7	22.7	NUM
eurjchem-788	66	112	(	(	PUNCT
eurjchem-788	66	113	1c	1c	NOUN
eurjchem-788	66	114	,	,	PUNCT
eurjchem-788	66	115	thienyl‐ch2‐ch2‐ch2‐ch2‐	thienyl‐ch2‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	66	116	)	)	PUNCT
eurjchem-788	66	117	,	,	PUNCT
eurjchem-788	66	118	21.4	21.4	NUM
eurjchem-788	66	119	(	(	PUNCT
eurjchem-788	66	120	1c	1c	NOUN
eurjchem-788	66	121	,	,	PUNCT
eurjchem-788	66	122	thienyl‐ch2‐ch2‐ch2‐	thienyl‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	66	123	ch2‐	ch2‐	NOUN
eurjchem-788	66	124	)	)	PUNCT
eurjchem-788	66	125	,	,	PUNCT
eurjchem-788	66	126	20.9	20.9	NUM
eurjchem-788	66	127	(	(	PUNCT
eurjchem-788	66	128	1c	1c	NOUN
eurjchem-788	66	129	,	,	PUNCT
eurjchem-788	66	130	pyridinyl‐ch2‐ch2‐	pyridinyl‐ch2‐ch2‐	NUM
eurjchem-788	66	131	)	)	PUNCT
eurjchem-788	66	132	.	.	PUNCT
eurjchem-788	67	1	anal	anal	PROPN
eurjchem-788	67	2	.	.	PUNCT
eurjchem-788	67	3	calcd	calcd	NOUN
eurjchem-788	67	4	.	.	PUNCT
eurjchem-788	68	1	for	for	ADP
eurjchem-788	68	2	c15h16n2os	c15h16n2o	NOUN
eurjchem-788	68	3	:	:	PUNCT
eurjchem-788	68	4	c	c	X
eurjchem-788	68	5	,	,	PUNCT
eurjchem-788	68	6	66.15	66.15	NUM
eurjchem-788	68	7	;	;	PUNCT
eurjchem-788	68	8	h	h	NOUN
eurjchem-788	68	9	,	,	PUNCT
eurjchem-788	68	10	5.92	5.92	NUM
eurjchem-788	68	11	;	;	PUNCT
eurjchem-788	68	12	n	n	CCONJ
eurjchem-788	68	13	,	,	PUNCT
eurjchem-788	68	14	10.29	10.29	NUM
eurjchem-788	68	15	.	.	PUNCT
eurjchem-788	68	16	found	find	VERB
eurjchem-788	68	17	:	:	PUNCT
eurjchem-788	69	1	c	c	X
eurjchem-788	69	2	,	,	PUNCT
eurjchem-788	69	3	66.08	66.08	NUM
eurjchem-788	69	4	;	;	PUNCT
eurjchem-788	69	5	h	h	NOUN
eurjchem-788	69	6	,	,	PUNCT
eurjchem-788	69	7	5.85	5.85	NUM
eurjchem-788	69	8	;	;	PUNCT
eurjchem-788	69	9	n	n	CCONJ
eurjchem-788	69	10	,	,	PUNCT
eurjchem-788	69	11	10.34	10.34	NUM
eurjchem-788	69	12	%	%	NOUN
eurjchem-788	69	13	.	.	PUNCT
eurjchem-788	70	1	4‐amino‐2,3‐dimethyl‐7,8‐dihydro‐6h‐thieno[2,3‐b]quinolin‐	4‐amino‐2,3‐dimethyl‐7,8‐dihydro‐6h‐thieno[2,3‐b]quinolin‐	NOUN
eurjchem-788	70	2	5‐one	5‐one	NUM
eurjchem-788	70	3	(	(	PUNCT
eurjchem-788	70	4	2b	2b	NOUN
eurjchem-788	70	5	):	):	PUNCT
eurjchem-788	70	6	following	follow	VERB
eurjchem-788	70	7	the	the	DET
eurjchem-788	70	8	general	general	ADJ
eurjchem-788	70	9	method	method	NOUN
eurjchem-788	70	10	for	for	ADP
eurjchem-788	70	11	the	the	DET
eurjchem-788	70	12	friedländer	friedländer	NOUN
eurjchem-788	70	13	reaction	reaction	NOUN
eurjchem-788	70	14	,	,	PUNCT
eurjchem-788	70	15	alcl3	alcl3	PROPN
eurjchem-788	71	1	(	(	PUNCT
eurjchem-788	71	2	800	800	NUM
eurjchem-788	71	3	mg	mg	NUM
eurjchem-788	71	4	)	)	PUNCT
eurjchem-788	71	5	or	or	CCONJ
eurjchem-788	71	6	activated	activate	VERB
eurjchem-788	71	7	bentonite	bentonite	NOUN
eurjchem-788	71	8	(	(	PUNCT
eurjchem-788	71	9	1000	1000	NUM
eurjchem-788	71	10	mg	mg	NOUN
eurjchem-788	71	11	)	)	PUNCT
eurjchem-788	71	12	in	in	ADP
eurjchem-788	71	13	dry	dry	ADJ
eurjchem-788	71	14	1,2‐dichloroethane	1,2‐dichloroethane	NOUN
eurjchem-788	71	15	(	(	PUNCT
eurjchem-788	71	16	50	50	NUM
eurjchem-788	71	17	ml	ml	NOUN
eurjchem-788	71	18	)	)	PUNCT
eurjchem-788	71	19	was	be	AUX
eurjchem-788	71	20	reacted	react	VERB
eurjchem-788	71	21	with	with	ADP
eurjchem-788	71	22	cyclohexane‐	cyclohexane‐	PROPN
eurjchem-788	71	23	1,3‐dione	1,3‐dione	NUM
eurjchem-788	71	24	(	(	PUNCT
eurjchem-788	71	25	10	10	NUM
eurjchem-788	71	26	mmol	mmol	NOUN
eurjchem-788	71	27	)	)	PUNCT
eurjchem-788	71	28	and	and	CCONJ
eurjchem-788	71	29	aminothiophene	aminothiophene	VERB
eurjchem-788	71	30	1b	1b	NUM
eurjchem-788	71	31	(	(	PUNCT
eurjchem-788	71	32	5	5	NUM
eurjchem-788	71	33	mmol	mmol	NOUN
eurjchem-788	71	34	)	)	PUNCT
eurjchem-788	71	35	.	.	PUNCT
eurjchem-788	72	1	the	the	DET
eurjchem-788	72	2	mixture	mixture	NOUN
eurjchem-788	72	3	was	be	AUX
eurjchem-788	72	4	refluxed	refluxe	VERB
eurjchem-788	72	5	for	for	ADP
eurjchem-788	72	6	24	24	NUM
eurjchem-788	72	7	h.	h.	PROPN
eurjchem-788	72	8	work‐up	work‐up	PROPN
eurjchem-788	72	9	and	and	CCONJ
eurjchem-788	72	10	chromatography	chromatography	NOUN
eurjchem-788	72	11	provided	provide	VERB
eurjchem-788	72	12	compound	compound	NOUN
eurjchem-788	72	13	2b	2b	NOUN
eurjchem-788	72	14	.	.	PUNCT
eurjchem-788	73	1	color	color	NOUN
eurjchem-788	73	2	:	:	PUNCT
eurjchem-788	73	3	brown	brown	ADJ
eurjchem-788	73	4	.	.	PUNCT
eurjchem-788	74	1	yield	yield	NOUN
eurjchem-788	74	2	:	:	PUNCT
eurjchem-788	74	3	71	71	NUM
eurjchem-788	74	4	%	%	NOUN
eurjchem-788	74	5	.	.	PUNCT
eurjchem-788	75	1	m.p	m.p	PROPN
eurjchem-788	75	2	.	.	PROPN
eurjchem-788	75	3	:	:	PUNCT
eurjchem-788	76	1	202‐	202‐	NUM
eurjchem-788	76	2	204	204	NUM
eurjchem-788	76	3	°	°	NUM
eurjchem-788	76	4	c	c	X
eurjchem-788	76	5	.	.	PUNCT
eurjchem-788	77	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	77	2	(	(	PUNCT
eurjchem-788	77	3	kbr	kbr	PROPN
eurjchem-788	77	4	,	,	PUNCT
eurjchem-788	77	5	ν	ν	PROPN
eurjchem-788	77	6	,	,	PUNCT
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eurjchem-788	77	8	):	):	PUNCT
eurjchem-788	77	9	3397	3397	NUM
eurjchem-788	77	10	,	,	PUNCT
eurjchem-788	77	11	3216	3216	NUM
eurjchem-788	77	12	(nh	(nh	NOUN
eurjchem-788	77	13	)	)	PUNCT
eurjchem-788	77	14	(	(	PUNCT
eurjchem-788	77	15	nh2	nh2	PROPN
eurjchem-788	77	16	)	)	PUNCT
eurjchem-788	77	17	,	,	PUNCT
eurjchem-788	77	18	1638	1638	NUM
eurjchem-788	77	19	(co	(co	NOUN
eurjchem-788	77	20	)	)	PUNCT
eurjchem-788	77	21	,	,	PUNCT
eurjchem-788	77	22	1587	1587	NUM
eurjchem-788	77	23	(nh	(nh	NOUN
eurjchem-788	77	24	)	)	PUNCT
eurjchem-788	77	25	(	(	PUNCT
eurjchem-788	77	26	nh2	nh2	PROPN
eurjchem-788	77	27	)	)	PUNCT
eurjchem-788	77	28	,	,	PUNCT
eurjchem-788	77	29	1422	1422	NUM
eurjchem-788	77	30	(ch	(ch	NOUN
eurjchem-788	77	31	)	)	PUNCT
eurjchem-788	77	32	(	(	PUNCT
eurjchem-788	77	33	ch2	ch2	PROPN
eurjchem-788	77	34	)	)	PUNCT
eurjchem-788	77	35	.	.	PUNCT
eurjchem-788	78	1	1h	1h	NUM
eurjchem-788	78	2	nmr	nmr	NOUN
eurjchem-788	78	3	(	(	PUNCT
eurjchem-788	78	4	300	300	NUM
eurjchem-788	78	5	mhz	mhz	NOUN
eurjchem-788	78	6	,	,	PUNCT
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eurjchem-788	78	8	,	,	PUNCT
eurjchem-788	78	9	δ	δ	PROPN
eurjchem-788	78	10	,	,	PUNCT
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eurjchem-788	78	12	):	):	PUNCT
eurjchem-788	78	13	5.33	5.33	NUM
eurjchem-788	78	14	(	(	PUNCT
eurjchem-788	78	15	s	s	PROPN
eurjchem-788	78	16	,	,	PUNCT
eurjchem-788	78	17	br	br	PROPN
eurjchem-788	78	18	,	,	PUNCT
eurjchem-788	78	19	1h	1h	NUM
eurjchem-788	78	20	,	,	PUNCT
eurjchem-788	78	21	nh2	nh2	PROPN
eurjchem-788	78	22	)	)	PUNCT
eurjchem-788	78	23	,	,	PUNCT
eurjchem-788	78	24	2.97	2.97	NUM
eurjchem-788	78	25	(	(	PUNCT
eurjchem-788	78	26	m	m	PROPN
eurjchem-788	78	27	,	,	PUNCT
eurjchem-788	78	28	2h	2h	NUM
eurjchem-788	78	29	,	,	PUNCT
eurjchem-788	78	30	‐ch2‐co‐	‐ch2‐co‐	NOUN
eurjchem-788	78	31	)	)	PUNCT
eurjchem-788	78	32	,	,	PUNCT
eurjchem-788	78	33	2.72	2.72	NUM
eurjchem-788	78	34	(	(	PUNCT
eurjchem-788	78	35	m	m	PROPN
eurjchem-788	78	36	,	,	PUNCT
eurjchem-788	78	37	2h	2h	NUM
eurjchem-788	78	38	,	,	PUNCT
eurjchem-788	78	39	=	=	NOUN
eurjchem-788	78	40	c‐ch2	c‐ch2	PROPN
eurjchem-788	78	41	)	)	PUNCT
eurjchem-788	78	42	,	,	PUNCT
eurjchem-788	78	43	2.53	2.53	NUM
eurjchem-788	78	44	(	(	PUNCT
eurjchem-788	78	45	m	m	PROPN
eurjchem-788	78	46	,	,	PUNCT
eurjchem-788	78	47	3h	3h	NUM
eurjchem-788	78	48	,	,	PUNCT
eurjchem-788	78	49	ch3	ch3	PROPN
eurjchem-788	78	50	)	)	PUNCT
eurjchem-788	78	51	,	,	PUNCT
eurjchem-788	78	52	2.37	2.37	NUM
eurjchem-788	78	53	(	(	PUNCT
eurjchem-788	78	54	m	m	PROPN
eurjchem-788	78	55	,	,	PUNCT
eurjchem-788	78	56	3h	3h	NUM
eurjchem-788	78	57	,	,	PUNCT
eurjchem-788	78	58	ch3	ch3	PROPN
eurjchem-788	78	59	)	)	PUNCT
eurjchem-788	78	60	,	,	PUNCT
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eurjchem-788	78	62	(	(	PUNCT
eurjchem-788	78	63	m	m	PROPN
eurjchem-788	78	64	,	,	PUNCT
eurjchem-788	78	65	2h	2h	NUM
eurjchem-788	78	66	,	,	PUNCT
eurjchem-788	78	67	‐ch2‐ch2‐ch2‐co‐	‐ch2‐ch2‐ch2‐co‐	PROPN
eurjchem-788	78	68	)	)	PUNCT
eurjchem-788	78	69	,	,	PUNCT
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eurjchem-788	78	71	(	(	PUNCT
eurjchem-788	78	72	s	s	PROPN
eurjchem-788	78	73	,	,	PUNCT
eurjchem-788	78	74	br	br	PROPN
eurjchem-788	78	75	,	,	PUNCT
eurjchem-788	78	76	1h	1h	NUM
eurjchem-788	78	77	,	,	PUNCT
eurjchem-788	78	78	nh2	nh2	PROPN
eurjchem-788	78	79	linked	link	VERB
eurjchem-788	78	80	h‐	h‐	NOUN
eurjchem-788	78	81	bonding	bonding	NOUN
eurjchem-788	78	82	to	to	PART
eurjchem-788	78	83	co	co	VERB
eurjchem-788	78	84	)	)	PUNCT
eurjchem-788	78	85	.	.	PUNCT
eurjchem-788	79	1	13c	13c	NOUN
eurjchem-788	79	2	nmr	nmr	NOUN
eurjchem-788	79	3	(	(	PUNCT
eurjchem-788	79	4	75	75	NUM
eurjchem-788	79	5	mhz	mhz	NOUN
eurjchem-788	79	6	,	,	PUNCT
eurjchem-788	79	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	79	8	,	,	PUNCT
eurjchem-788	79	9	δ	δ	PROPN
eurjchem-788	79	10	,	,	PUNCT
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eurjchem-788	79	12	):	):	PUNCT
eurjchem-788	79	13	201.2	201.2	NUM
eurjchem-788	79	14	(	(	PUNCT
eurjchem-788	79	15	1c	1c	NOUN
eurjchem-788	79	16	,	,	PUNCT
eurjchem-788	79	17	co	co	NOUN
eurjchem-788	79	18	)	)	PUNCT
eurjchem-788	79	19	,	,	PUNCT
eurjchem-788	79	20	162.1	162.1	NUM
eurjchem-788	79	21	(	(	PUNCT
eurjchem-788	79	22	1c	1c	NOUN
eurjchem-788	79	23	,	,	PUNCT
eurjchem-788	79	24	‐s‐c	‐s‐c	ADJ
eurjchem-788	79	25	=	=	SYM
eurjchem-788	79	26	c(n)‐	c(n)‐	NOUN
eurjchem-788	79	27	)	)	PUNCT
eurjchem-788	79	28	,	,	PUNCT
eurjchem-788	79	29	161.6	161.6	NUM
eurjchem-788	79	30	(	(	PUNCT
eurjchem-788	79	31	1c	1c	NOUN
eurjchem-788	79	32	,	,	PUNCT
eurjchem-788	79	33	‐n	‐n	ADJ
eurjchem-788	79	34	=	=	NOUN
eurjchem-788	79	35	c‐ch2‐	c‐ch2‐	PROPN
eurjchem-788	79	36	)	)	PUNCT
eurjchem-788	79	37	,	,	PUNCT
eurjchem-788	79	38	152.6	152.6	NUM
eurjchem-788	79	39	(	(	PUNCT
eurjchem-788	79	40	1c	1c	X
eurjchem-788	79	41	,	,	PUNCT
eurjchem-788	79	42	=	=	NOUN
eurjchem-788	79	43	c‐nh2	c‐nh2	PROPN
eurjchem-788	79	44	)	)	PUNCT
eurjchem-788	79	45	,	,	PUNCT
eurjchem-788	79	46	138.2	138.2	NUM
eurjchem-788	79	47	(	(	PUNCT
eurjchem-788	79	48	1c	1c	NOUN
eurjchem-788	79	49	,	,	PUNCT
eurjchem-788	79	50	‐c	‐c	NOUN
eurjchem-788	79	51	=	=	NOUN
eurjchem-788	79	52	c‐s	c‐s	NOUN
eurjchem-788	79	53	)	)	PUNCT
eurjchem-788	79	54	,	,	PUNCT
eurjchem-788	79	55	125.6	125.6	NUM
eurjchem-788	79	56	(	(	PUNCT
eurjchem-788	79	57	1c	1c	NOUN
eurjchem-788	79	58	,	,	PUNCT
eurjchem-788	79	59	‐c	‐c	NOUN
eurjchem-788	79	60	=	=	NOUN
eurjchem-788	79	61	c‐s	c‐s	NOUN
eurjchem-788	79	62	)	)	PUNCT
eurjchem-788	79	63	,	,	PUNCT
eurjchem-788	79	64	121.9	121.9	NUM
eurjchem-788	79	65	(	(	PUNCT
eurjchem-788	79	66	1c	1c	NOUN
eurjchem-788	79	67	,	,	PUNCT
eurjchem-788	79	68	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	79	69	=	=	NOUN
eurjchem-788	79	70	c‐c‐nh2	c‐c‐nh2	PROPN
eurjchem-788	79	71	)	)	PUNCT
eurjchem-788	79	72	,	,	PUNCT
eurjchem-788	79	73	112.5	112.5	NUM
eurjchem-788	79	74	(	(	PUNCT
eurjchem-788	79	75	1c	1c	NOUN
eurjchem-788	79	76	,	,	PUNCT
eurjchem-788	79	77	pyridinyl‐c‐co	pyridinyl‐c‐co	PRON
eurjchem-788	79	78	)	)	PUNCT
eurjchem-788	79	79	,	,	PUNCT
eurjchem-788	79	80	39.9	39.9	NUM
eurjchem-788	79	81	(	(	PUNCT
eurjchem-788	79	82	1c	1c	NOUN
eurjchem-788	79	83	,	,	PUNCT
eurjchem-788	79	84	‐ch2‐	‐ch2‐	PROPN
eurjchem-788	79	85	co	co	NOUN
eurjchem-788	79	86	)	)	PUNCT
eurjchem-788	79	87	,	,	PUNCT
eurjchem-788	79	88	29.8	29.8	NUM
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eurjchem-788	79	90	1c	1c	NOUN
eurjchem-788	79	91	,	,	PUNCT
eurjchem-788	79	92	‐ch2‐ch2‐co	‐ch2‐ch2‐co	NOUN
eurjchem-788	79	93	)	)	PUNCT
eurjchem-788	79	94	,	,	PUNCT
eurjchem-788	79	95	21.4	21.4	NUM
eurjchem-788	79	96	(	(	PUNCT
eurjchem-788	79	97	1c	1c	NOUN
eurjchem-788	79	98	,	,	PUNCT
eurjchem-788	79	99	pyridinyl‐ch2‐ch2‐	pyridinyl‐ch2‐ch2‐	NUM
eurjchem-788	79	100	)	)	PUNCT
eurjchem-788	79	101	,	,	PUNCT
eurjchem-788	79	102	14.8	14.8	NUM
eurjchem-788	79	103	(	(	PUNCT
eurjchem-788	79	104	1c	1c	X
eurjchem-788	79	105	,	,	PUNCT
eurjchem-788	79	106	ch3	ch3	PROPN
eurjchem-788	79	107	)	)	PUNCT
eurjchem-788	79	108	,	,	PUNCT
eurjchem-788	79	109	13.1	13.1	NUM
eurjchem-788	79	110	(	(	PUNCT
eurjchem-788	79	111	1c	1c	NOUN
eurjchem-788	79	112	,	,	PUNCT
eurjchem-788	79	113	ch3	ch3	PROPN
eurjchem-788	79	114	)	)	PUNCT
eurjchem-788	79	115	.	.	PUNCT
eurjchem-788	80	1	anal	anal	PROPN
eurjchem-788	80	2	.	.	PUNCT
eurjchem-788	80	3	calcd	calcd	NOUN
eurjchem-788	80	4	.	.	PUNCT
eurjchem-788	81	1	for	for	ADP
eurjchem-788	81	2	c13h14n2os	c13h14n2o	NOUN
eurjchem-788	81	3	:	:	PUNCT
eurjchem-788	81	4	c	c	X
eurjchem-788	81	5	,	,	PUNCT
eurjchem-788	81	6	63.39	63.39	NUM
eurjchem-788	81	7	;	;	PUNCT
eurjchem-788	81	8	h	h	NOUN
eurjchem-788	81	9	,	,	PUNCT
eurjchem-788	81	10	5.73	5.73	NUM
eurjchem-788	81	11	;	;	PUNCT
eurjchem-788	81	12	n	n	CCONJ
eurjchem-788	81	13	,	,	PUNCT
eurjchem-788	81	14	11.37	11.37	NUM
eurjchem-788	81	15	.	.	PUNCT
eurjchem-788	81	16	found	find	VERB
eurjchem-788	81	17	:	:	PUNCT
eurjchem-788	82	1	c	c	X
eurjchem-788	82	2	,	,	PUNCT
eurjchem-788	82	3	63.43	63.43	NUM
eurjchem-788	82	4	;	;	PUNCT
eurjchem-788	82	5	h	h	NOUN
eurjchem-788	82	6	,	,	PUNCT
eurjchem-788	82	7	5.68	5.68	NUM
eurjchem-788	82	8	;	;	PUNCT
eurjchem-788	82	9	n	n	CCONJ
eurjchem-788	82	10	,	,	PUNCT
eurjchem-788	82	11	10.41	10.41	NUM
eurjchem-788	82	12	%	%	NOUN
eurjchem-788	82	13	.	.	PUNCT
eurjchem-788	83	1	4‐amino‐3‐(4‐chlorophenyl)‐7,8‐dihydro‐6h‐thieno[2,3‐b	4‐amino‐3‐(4‐chlorophenyl)‐7,8‐dihydro‐6h‐thieno[2,3‐b	NUM
eurjchem-788	83	2	]	]	X
eurjchem-788	84	1	quinolin‐5‐one	quinolin‐5‐one	PROPN
eurjchem-788	84	2	(	(	PUNCT
eurjchem-788	84	3	2c	2c	NUM
eurjchem-788	84	4	):	):	PUNCT
eurjchem-788	84	5	following	follow	VERB
eurjchem-788	84	6	the	the	DET
eurjchem-788	84	7	general	general	ADJ
eurjchem-788	84	8	method	method	NOUN
eurjchem-788	84	9	for	for	ADP
eurjchem-788	84	10	the	the	DET
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eurjchem-788	84	12	reaction	reaction	NOUN
eurjchem-788	84	13	,	,	PUNCT
eurjchem-788	84	14	alcl3	alcl3	PROPN
eurjchem-788	85	1	(	(	PUNCT
eurjchem-788	85	2	800	800	NUM
eurjchem-788	85	3	mg	mg	NUM
eurjchem-788	85	4	)	)	PUNCT
eurjchem-788	85	5	or	or	CCONJ
eurjchem-788	85	6	activated	activate	VERB
eurjchem-788	85	7	bentonite	bentonite	NOUN
eurjchem-788	85	8	(	(	PUNCT
eurjchem-788	85	9	1000	1000	NUM
eurjchem-788	85	10	mg	mg	NOUN
eurjchem-788	85	11	)	)	PUNCT
eurjchem-788	85	12	in	in	ADP
eurjchem-788	85	13	dry	dry	ADJ
eurjchem-788	85	14	1,2‐dichloroethane	1,2‐dichloroethane	NOUN
eurjchem-788	85	15	(	(	PUNCT
eurjchem-788	85	16	50	50	NUM
eurjchem-788	85	17	ml	ml	NOUN
eurjchem-788	85	18	)	)	PUNCT
eurjchem-788	85	19	was	be	AUX
eurjchem-788	85	20	reacted	react	VERB
eurjchem-788	85	21	with	with	ADP
eurjchem-788	85	22	cyclohexane‐1,3‐dione	cyclohexane‐1,3‐dione	PROPN
eurjchem-788	85	23	(	(	PUNCT
eurjchem-788	85	24	10	10	NUM
eurjchem-788	85	25	mmol	mmol	NOUN
eurjchem-788	85	26	)	)	PUNCT
eurjchem-788	85	27	and	and	CCONJ
eurjchem-788	85	28	aminothiophene	aminothiophene	NOUN
eurjchem-788	85	29	1c	1c	NOUN
eurjchem-788	85	30	(	(	PUNCT
eurjchem-788	85	31	5	5	NUM
eurjchem-788	85	32	mmol	mmol	NOUN
eurjchem-788	85	33	)	)	PUNCT
eurjchem-788	85	34	.	.	PUNCT
eurjchem-788	86	1	the	the	DET
eurjchem-788	86	2	mixture	mixture	NOUN
eurjchem-788	86	3	was	be	AUX
eurjchem-788	86	4	refluxed	refluxe	VERB
eurjchem-788	86	5	for	for	ADP
eurjchem-788	86	6	24	24	NUM
eurjchem-788	86	7	h.	h.	PROPN
eurjchem-788	86	8	work‐up	work‐up	PROPN
eurjchem-788	86	9	and	and	CCONJ
eurjchem-788	86	10	chromatography	chromatography	NOUN
eurjchem-788	86	11	provided	provide	VERB
eurjchem-788	86	12	compound	compound	NOUN
eurjchem-788	86	13	2c	2c	NOUN
eurjchem-788	86	14	.	.	PUNCT
eurjchem-788	87	1	color	color	NOUN
eurjchem-788	87	2	:	:	PUNCT
eurjchem-788	87	3	brown	brown	ADJ
eurjchem-788	87	4	.	.	PUNCT
eurjchem-788	88	1	yield	yield	NOUN
eurjchem-788	88	2	:	:	PUNCT
eurjchem-788	88	3	64	64	NUM
eurjchem-788	88	4	%	%	NOUN
eurjchem-788	88	5	.	.	PUNCT
eurjchem-788	89	1	m.p	m.p	PROPN
eurjchem-788	89	2	.	.	PROPN
eurjchem-788	89	3	:	:	PUNCT
eurjchem-788	90	1	234‐236	234‐236	PROPN
eurjchem-788	90	2	°	°	SYM
eurjchem-788	90	3	c	c	PROPN
eurjchem-788	90	4	.	.	PUNCT
eurjchem-788	91	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	91	2	(	(	PUNCT
eurjchem-788	91	3	kbr	kbr	PROPN
eurjchem-788	91	4	,	,	PUNCT
eurjchem-788	91	5	ν	ν	PROPN
eurjchem-788	91	6	,	,	PUNCT
eurjchem-788	91	7	cm‐1	cm‐1	PROPN
eurjchem-788	91	8	):	):	PUNCT
eurjchem-788	91	9	3396	3396	NUM
eurjchem-788	91	10	,	,	PUNCT
eurjchem-788	91	11	3212	3212	NUM
eurjchem-788	91	12	(nh	(nh	PROPN
eurjchem-788	91	13	)	)	PUNCT
eurjchem-788	91	14	(	(	PUNCT
eurjchem-788	91	15	nh2	nh2	PROPN
eurjchem-788	91	16	)	)	PUNCT
eurjchem-788	91	17	,	,	PUNCT
eurjchem-788	91	18	1636	1636	NUM
eurjchem-788	91	19	(co	(co	NOUN
eurjchem-788	91	20	)	)	PUNCT
eurjchem-788	91	21	,	,	PUNCT
eurjchem-788	91	22	1587	1587	NUM
eurjchem-788	91	23	(nh	(nh	NOUN
eurjchem-788	91	24	)	)	PUNCT
eurjchem-788	91	25	(	(	PUNCT
eurjchem-788	91	26	nh2	nh2	PROPN
eurjchem-788	91	27	)	)	PUNCT
eurjchem-788	91	28	,	,	PUNCT
eurjchem-788	91	29	831	831	NUM
eurjchem-788	91	30	(	(	PUNCT
eurjchem-788	91	31	c‐cl	c‐cl	PROPN
eurjchem-788	91	32	)	)	PUNCT
eurjchem-788	91	33	,	,	PUNCT
eurjchem-788	91	34	765	765	NUM
eurjchem-788	91	35	(	(	PUNCT
eurjchem-788	91	36	disubstituted	disubstitute	VERB
eurjchem-788	91	37	phenyl	phenyl	NOUN
eurjchem-788	91	38	)	)	PUNCT
eurjchem-788	91	39	.	.	PUNCT
eurjchem-788	92	1	1h	1h	NUM
eurjchem-788	92	2	nmr	nmr	NOUN
eurjchem-788	92	3	(	(	PUNCT
eurjchem-788	92	4	300	300	NUM
eurjchem-788	92	5	mhz	mhz	NOUN
eurjchem-788	92	6	,	,	PUNCT
eurjchem-788	92	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	92	8	,	,	PUNCT
eurjchem-788	92	9	δ	δ	PROPN
eurjchem-788	92	10	,	,	PUNCT
eurjchem-788	92	11	ppm	ppm	NUM
eurjchem-788	92	12	):	):	PUNCT
eurjchem-788	92	13	7.36	7.36	NUM
eurjchem-788	92	14	(	(	PUNCT
eurjchem-788	92	15	m	m	PROPN
eurjchem-788	92	16	,	,	PUNCT
eurjchem-788	92	17	4h	4h	NUM
eurjchem-788	92	18	,	,	PUNCT
eurjchem-788	92	19	ar‐h	ar‐h	PROPN
eurjchem-788	92	20	)	)	PUNCT
eurjchem-788	92	21	,	,	PUNCT
eurjchem-788	92	22	6.86	6.86	NUM
eurjchem-788	92	23	(	(	PUNCT
eurjchem-788	92	24	s	s	PROPN
eurjchem-788	92	25	,	,	PUNCT
eurjchem-788	92	26	1h	1h	NUM
eurjchem-788	92	27	,	,	PUNCT
eurjchem-788	92	28	thienyl‐h	thienyl‐h	PROPN
eurjchem-788	92	29	)	)	PUNCT
eurjchem-788	92	30	,	,	PUNCT
eurjchem-788	92	31	5.28	5.28	NUM
eurjchem-788	92	32	(	(	PUNCT
eurjchem-788	92	33	s	s	PROPN
eurjchem-788	92	34	,	,	PUNCT
eurjchem-788	92	35	br	br	PROPN
eurjchem-788	92	36	,	,	PUNCT
eurjchem-788	92	37	1h	1h	NUM
eurjchem-788	92	38	,	,	PUNCT
eurjchem-788	92	39	nh2	nh2	PROPN
eurjchem-788	92	40	)	)	PUNCT
eurjchem-788	92	41	,	,	PUNCT
eurjchem-788	92	42	2.91	2.91	NUM
eurjchem-788	92	43	(	(	PUNCT
eurjchem-788	92	44	m	m	PROPN
eurjchem-788	92	45	,	,	PUNCT
eurjchem-788	92	46	2h	2h	NUM
eurjchem-788	92	47	,	,	PUNCT
eurjchem-788	92	48	n	n	CCONJ
eurjchem-788	92	49	=	=	SYM
eurjchem-788	92	50	c‐ch2	c‐ch2	PROPN
eurjchem-788	92	51	)	)	PUNCT
eurjchem-788	92	52	,	,	PUNCT
eurjchem-788	92	53	2.63	2.63	NUM
eurjchem-788	92	54	(	(	PUNCT
eurjchem-788	92	55	m	m	PROPN
eurjchem-788	92	56	,	,	PUNCT
eurjchem-788	92	57	2h	2h	NUM
eurjchem-788	92	58	,	,	PUNCT
eurjchem-788	92	59	‐ch2‐co‐	‐ch2‐co‐	NOUN
eurjchem-788	92	60	)	)	PUNCT
eurjchem-788	92	61	,	,	PUNCT
eurjchem-788	92	62	2.07	2.07	NUM
eurjchem-788	92	63	(	(	PUNCT
eurjchem-788	92	64	m	m	PROPN
eurjchem-788	92	65	,	,	PUNCT
eurjchem-788	92	66	2h	2h	NUM
eurjchem-788	92	67	,	,	PUNCT
eurjchem-788	92	68	‐	‐	ADV
eurjchem-788	92	69	ch2‐ch2‐ch2‐co‐	ch2‐ch2‐ch2‐co‐	ADJ
eurjchem-788	92	70	)	)	PUNCT
eurjchem-788	92	71	,	,	PUNCT
eurjchem-788	92	72	1.42	1.42	NUM
eurjchem-788	92	73	(	(	PUNCT
eurjchem-788	92	74	s	s	PROPN
eurjchem-788	92	75	,	,	PUNCT
eurjchem-788	92	76	br	br	PROPN
eurjchem-788	92	77	,	,	PUNCT
eurjchem-788	92	78	1h	1h	NUM
eurjchem-788	92	79	,	,	PUNCT
eurjchem-788	92	80	nh2	nh2	PROPN
eurjchem-788	92	81	linked	link	VERB
eurjchem-788	92	82	h‐bonding	h‐bonde	VERB
eurjchem-788	92	83	to	to	PART
eurjchem-788	92	84	co	co	VERB
eurjchem-788	92	85	)	)	PUNCT
eurjchem-788	92	86	.	.	PUNCT
eurjchem-788	93	1	13c	13c	NOUN
eurjchem-788	93	2	nmr	nmr	NOUN
eurjchem-788	93	3	(	(	PUNCT
eurjchem-788	93	4	75	75	NUM
eurjchem-788	93	5	mhz	mhz	NOUN
eurjchem-788	93	6	,	,	PUNCT
eurjchem-788	93	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	93	8	,	,	PUNCT
eurjchem-788	93	9	δ	δ	PROPN
eurjchem-788	93	10	,	,	PUNCT
eurjchem-788	93	11	ppm	ppm	NUM
eurjchem-788	93	12	):	):	PUNCT
eurjchem-788	93	13	198.3	198.3	NUM
eurjchem-788	93	14	(	(	PUNCT
eurjchem-788	93	15	1c	1c	NOUN
eurjchem-788	93	16	,	,	PUNCT
eurjchem-788	93	17	co	co	NOUN
eurjchem-788	93	18	)	)	PUNCT
eurjchem-788	93	19	,	,	PUNCT
eurjchem-788	93	20	161.8	161.8	NUM
eurjchem-788	93	21	(	(	PUNCT
eurjchem-788	93	22	1c	1c	NOUN
eurjchem-788	93	23	,	,	PUNCT
eurjchem-788	93	24	‐s‐c	‐s‐c	ADJ
eurjchem-788	93	25	=	=	SYM
eurjchem-788	93	26	c(n)‐	c(n)‐	NOUN
eurjchem-788	93	27	)	)	PUNCT
eurjchem-788	93	28	,	,	PUNCT
eurjchem-788	93	29	160.1	160.1	NUM
eurjchem-788	93	30	(	(	PUNCT
eurjchem-788	93	31	1c	1c	NOUN
eurjchem-788	93	32	,	,	PUNCT
eurjchem-788	93	33	‐n	‐n	ADJ
eurjchem-788	93	34	=	=	NOUN
eurjchem-788	93	35	c‐ch2‐	c‐ch2‐	PROPN
eurjchem-788	93	36	)	)	PUNCT
eurjchem-788	93	37	,	,	PUNCT
eurjchem-788	93	38	154.3	154.3	NUM
eurjchem-788	93	39	(	(	PUNCT
eurjchem-788	93	40	1c	1c	NOUN
eurjchem-788	93	41	,	,	PUNCT
eurjchem-788	93	42	=	=	NOUN
eurjchem-788	93	43	c‐nh2	c‐nh2	PROPN
eurjchem-788	93	44	)	)	PUNCT
eurjchem-788	93	45	,	,	PUNCT
eurjchem-788	93	46	145.9	145.9	NUM
eurjchem-788	93	47	(	(	PUNCT
eurjchem-788	93	48	1c	1c	NOUN
eurjchem-788	93	49	,	,	PUNCT
eurjchem-788	93	50	‐c	‐c	NOUN
eurjchem-788	93	51	=	=	NOUN
eurjchem-788	93	52	c‐s	c‐s	NOUN
eurjchem-788	93	53	)	)	PUNCT
eurjchem-788	93	54	,	,	PUNCT
eurjchem-788	93	55	136.2	136.2	NUM
eurjchem-788	93	56	(	(	PUNCT
eurjchem-788	93	57	1c	1c	NOUN
eurjchem-788	93	58	,	,	PUNCT
eurjchem-788	93	59	c‐ar	c‐ar	NUM
eurjchem-788	93	60	)	)	PUNCT
eurjchem-788	93	61	,	,	PUNCT
eurjchem-788	93	62	135.6	135.6	NUM
eurjchem-788	93	63	(	(	PUNCT
eurjchem-788	93	64	1c	1c	NOUN
eurjchem-788	93	65	,	,	PUNCT
eurjchem-788	93	66	cl‐c‐ar	cl‐c‐ar	NOUN
eurjchem-788	93	67	)	)	PUNCT
eurjchem-788	93	68	,	,	PUNCT
eurjchem-788	93	69	134.2	134.2	NUM
eurjchem-788	93	70	(	(	PUNCT
eurjchem-788	93	71	2c	2c	NUM
eurjchem-788	93	72	,	,	PUNCT
eurjchem-788	93	73	218	218	NUM
eurjchem-788	93	74	dridi	dridi	PROPN
eurjchem-788	93	75	et	et	PROPN
eurjchem-788	93	76	al	al	PROPN
eurjchem-788	93	77	.	.	PUNCT
eurjchem-788	93	78	/	/	SYM
eurjchem-788	93	79	european	european	PROPN
eurjchem-788	93	80	journal	journal	PROPN
eurjchem-788	93	81	of	of	ADP
eurjchem-788	93	82	chemistry	chemistry	NOUN
eurjchem-788	93	83	4	4	NUM
eurjchem-788	93	84	(	(	PUNCT
eurjchem-788	93	85	3	3	NUM
eurjchem-788	93	86	)	)	PUNCT
eurjchem-788	93	87	(	(	PUNCT
eurjchem-788	93	88	2013	2013	NUM
eurjchem-788	93	89	)	)	PUNCT
eurjchem-788	93	90	216‐219	216‐219	ADJ
eurjchem-788	93	91	scheme	scheme	NOUN
eurjchem-788	93	92	2	2	NUM
eurjchem-788	93	93	ch‐ar	ch‐ar	NUM
eurjchem-788	93	94	)	)	PUNCT
eurjchem-788	93	95	,	,	PUNCT
eurjchem-788	93	96	129.3	129.3	NUM
eurjchem-788	93	97	(	(	PUNCT
eurjchem-788	93	98	2c	2c	NOUN
eurjchem-788	93	99	,	,	PUNCT
eurjchem-788	93	100	ch‐ar	ch‐ar	NUM
eurjchem-788	93	101	)	)	PUNCT
eurjchem-788	93	102	,	,	PUNCT
eurjchem-788	93	103	128.7	128.7	NUM
eurjchem-788	93	104	(	(	PUNCT
eurjchem-788	93	105	1c	1c	NOUN
eurjchem-788	93	106	,	,	PUNCT
eurjchem-788	93	107	‐c	‐c	NOUN
eurjchem-788	93	108	=	=	NOUN
eurjchem-788	93	109	c‐s	c‐s	NOUN
eurjchem-788	93	110	)	)	PUNCT
eurjchem-788	93	111	,	,	PUNCT
eurjchem-788	93	112	121.2	121.2	NUM
eurjchem-788	93	113	(	(	PUNCT
eurjchem-788	93	114	1c	1c	NOUN
eurjchem-788	93	115	,	,	PUNCT
eurjchem-788	93	116	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	93	117	=	=	NOUN
eurjchem-788	93	118	c‐c‐nh2	c‐c‐nh2	PROPN
eurjchem-788	93	119	)	)	PUNCT
eurjchem-788	93	120	,	,	PUNCT
eurjchem-788	93	121	115.2	115.2	NUM
eurjchem-788	93	122	(	(	PUNCT
eurjchem-788	93	123	1c	1c	NOUN
eurjchem-788	93	124	,	,	PUNCT
eurjchem-788	93	125	pyridinyl‐c‐co	pyridinyl‐c‐co	PRON
eurjchem-788	93	126	)	)	PUNCT
eurjchem-788	93	127	,	,	PUNCT
eurjchem-788	93	128	33.8	33.8	NUM
eurjchem-788	93	129	(	(	PUNCT
eurjchem-788	93	130	1c	1c	NOUN
eurjchem-788	93	131	,	,	PUNCT
eurjchem-788	93	132	‐ch2‐	‐ch2‐	PROPN
eurjchem-788	93	133	co	co	NOUN
eurjchem-788	93	134	)	)	PUNCT
eurjchem-788	93	135	,	,	PUNCT
eurjchem-788	93	136	25.4	25.4	NUM
eurjchem-788	93	137	(	(	PUNCT
eurjchem-788	93	138	1c	1c	NOUN
eurjchem-788	93	139	,	,	PUNCT
eurjchem-788	93	140	‐ch2‐ch2‐co	‐ch2‐ch2‐co	NOUN
eurjchem-788	93	141	)	)	PUNCT
eurjchem-788	93	142	,	,	PUNCT
eurjchem-788	93	143	22.7	22.7	NUM
eurjchem-788	93	144	(	(	PUNCT
eurjchem-788	93	145	1c	1c	NOUN
eurjchem-788	93	146	,	,	PUNCT
eurjchem-788	93	147	pyridinyl‐ch2‐ch2‐	pyridinyl‐ch2‐ch2‐	NUM
eurjchem-788	93	148	)	)	PUNCT
eurjchem-788	93	149	.	.	PUNCT
eurjchem-788	94	1	anal	anal	PROPN
eurjchem-788	94	2	.	.	PUNCT
eurjchem-788	94	3	calcd	calcd	NOUN
eurjchem-788	94	4	.	.	PUNCT
eurjchem-788	95	1	for	for	ADP
eurjchem-788	95	2	c17h13cln2os	c17h13cln2os	X
eurjchem-788	95	3	:	:	PUNCT
eurjchem-788	95	4	c	c	X
eurjchem-788	95	5	,	,	PUNCT
eurjchem-788	95	6	62.10	62.10	NUM
eurjchem-788	95	7	;	;	PUNCT
eurjchem-788	95	8	h	h	NOUN
eurjchem-788	95	9	,	,	PUNCT
eurjchem-788	95	10	3.98	3.98	NUM
eurjchem-788	95	11	;	;	PUNCT
eurjchem-788	95	12	n	n	CCONJ
eurjchem-788	95	13	,	,	PUNCT
eurjchem-788	95	14	8.52	8.52	NUM
eurjchem-788	95	15	.	.	PUNCT
eurjchem-788	96	1	found	find	VERB
eurjchem-788	96	2	:	:	PUNCT
eurjchem-788	97	1	c	c	X
eurjchem-788	97	2	,	,	PUNCT
eurjchem-788	97	3	62.14	62.14	NUM
eurjchem-788	97	4	;	;	PUNCT
eurjchem-788	97	5	h	h	X
eurjchem-788	97	6	,	,	PUNCT
eurjchem-788	97	7	4.01	4.01	NUM
eurjchem-788	97	8	;	;	PUNCT
eurjchem-788	97	9	n	n	CCONJ
eurjchem-788	97	10	,	,	PUNCT
eurjchem-788	97	11	8.47	8.47	NUM
eurjchem-788	97	12	%	%	NOUN
eurjchem-788	97	13	.	.	PUNCT
eurjchem-788	98	1	1‐[4‐amino‐3‐(4‐chlorophenyl)‐6‐methylthieno[2,3‐b	1‐[4‐amino‐3‐(4‐chlorophenyl)‐6‐methylthieno[2,3‐b	NUM
eurjchem-788	98	2	]	]	X
eurjchem-788	98	3	pyridin‐5‐yl]ethanone	pyridin‐5‐yl]ethanone	NOUN
eurjchem-788	98	4	(	(	PUNCT
eurjchem-788	98	5	2d	2d	NOUN
eurjchem-788	98	6	):	):	PUNCT
eurjchem-788	98	7	following	follow	VERB
eurjchem-788	98	8	the	the	DET
eurjchem-788	98	9	general	general	ADJ
eurjchem-788	98	10	method	method	NOUN
eurjchem-788	98	11	for	for	ADP
eurjchem-788	98	12	the	the	DET
eurjchem-788	98	13	friedländer	friedländer	NOUN
eurjchem-788	98	14	reaction	reaction	NOUN
eurjchem-788	98	15	,	,	PUNCT
eurjchem-788	98	16	alcl3	alcl3	X
eurjchem-788	98	17	(	(	PUNCT
eurjchem-788	98	18	800	800	NUM
eurjchem-788	98	19	mg	mg	NUM
eurjchem-788	98	20	)	)	PUNCT
eurjchem-788	98	21	or	or	CCONJ
eurjchem-788	98	22	activated	activate	VERB
eurjchem-788	98	23	bentonite	bentonite	NOUN
eurjchem-788	98	24	(	(	PUNCT
eurjchem-788	98	25	1000	1000	NUM
eurjchem-788	98	26	mg	mg	NOUN
eurjchem-788	98	27	)	)	PUNCT
eurjchem-788	98	28	in	in	ADP
eurjchem-788	98	29	dry	dry	ADJ
eurjchem-788	98	30	1,2‐dichloroethane	1,2‐dichloroethane	NOUN
eurjchem-788	98	31	(	(	PUNCT
eurjchem-788	98	32	50	50	NUM
eurjchem-788	98	33	ml	ml	NOUN
eurjchem-788	98	34	)	)	PUNCT
eurjchem-788	98	35	was	be	AUX
eurjchem-788	98	36	reacted	react	VERB
eurjchem-788	98	37	with	with	ADP
eurjchem-788	98	38	cyclohexane‐1,3‐dione	cyclohexane‐1,3‐dione	PROPN
eurjchem-788	98	39	(	(	PUNCT
eurjchem-788	98	40	10	10	NUM
eurjchem-788	98	41	mmol	mmol	NOUN
eurjchem-788	98	42	)	)	PUNCT
eurjchem-788	98	43	and	and	CCONJ
eurjchem-788	98	44	aminothiophene	aminothiophene	NOUN
eurjchem-788	98	45	1c	1c	NOUN
eurjchem-788	98	46	(	(	PUNCT
eurjchem-788	98	47	5	5	NUM
eurjchem-788	98	48	mmol	mmol	NOUN
eurjchem-788	98	49	)	)	PUNCT
eurjchem-788	98	50	.	.	PUNCT
eurjchem-788	99	1	the	the	DET
eurjchem-788	99	2	mixture	mixture	NOUN
eurjchem-788	99	3	was	be	AUX
eurjchem-788	99	4	refluxed	refluxe	VERB
eurjchem-788	99	5	for	for	ADP
eurjchem-788	99	6	24	24	NUM
eurjchem-788	99	7	h.	h.	PROPN
eurjchem-788	99	8	work‐up	work‐up	PROPN
eurjchem-788	99	9	and	and	CCONJ
eurjchem-788	99	10	chromatography	chromatography	NOUN
eurjchem-788	99	11	provided	provide	VERB
eurjchem-788	99	12	compound	compound	NOUN
eurjchem-788	99	13	2d	2d	NOUN
eurjchem-788	99	14	.	.	PUNCT
eurjchem-788	100	1	color	color	NOUN
eurjchem-788	100	2	:	:	PUNCT
eurjchem-788	100	3	brown	brown	ADJ
eurjchem-788	100	4	.	.	PUNCT
eurjchem-788	101	1	yield	yield	NOUN
eurjchem-788	101	2	:	:	PUNCT
eurjchem-788	101	3	73	73	NUM
eurjchem-788	101	4	%	%	NOUN
eurjchem-788	101	5	.	.	PUNCT
eurjchem-788	102	1	m.p	m.p	PROPN
eurjchem-788	102	2	.	.	PROPN
eurjchem-788	102	3	:	:	PUNCT
eurjchem-788	103	1	208‐210	208‐210	NUM
eurjchem-788	103	2	°	°	ADP
eurjchem-788	103	3	c	c	X
eurjchem-788	103	4	.	.	PUNCT
eurjchem-788	104	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	104	2	(	(	PUNCT
eurjchem-788	104	3	kbr	kbr	PROPN
eurjchem-788	104	4	,	,	PUNCT
eurjchem-788	104	5	ν	ν	PROPN
eurjchem-788	104	6	,	,	PUNCT
eurjchem-788	104	7	cm‐1	cm‐1	PROPN
eurjchem-788	104	8	):	):	PUNCT
eurjchem-788	104	9	3349	3349	NUM
eurjchem-788	104	10	,	,	PUNCT
eurjchem-788	104	11	3224	3224	NUM
eurjchem-788	104	12	(nh	(nh	PROPN
eurjchem-788	104	13	)	)	PUNCT
eurjchem-788	104	14	(	(	PUNCT
eurjchem-788	104	15	nh2	nh2	PROPN
eurjchem-788	104	16	)	)	PUNCT
eurjchem-788	104	17	,	,	PUNCT
eurjchem-788	104	18	1635	1635	NUM
eurjchem-788	104	19	(co	(co	NOUN
eurjchem-788	104	20	)	)	PUNCT
eurjchem-788	104	21	,	,	PUNCT
eurjchem-788	104	22	1589	1589	NUM
eurjchem-788	104	23	(nh	(nh	NOUN
eurjchem-788	104	24	)	)	PUNCT
eurjchem-788	104	25	(	(	PUNCT
eurjchem-788	104	26	nh2	nh2	PROPN
eurjchem-788	104	27	)	)	PUNCT
eurjchem-788	104	28	,	,	PUNCT
eurjchem-788	104	29	831	831	NUM
eurjchem-788	104	30	(	(	PUNCT
eurjchem-788	104	31	c‐cl	c‐cl	PROPN
eurjchem-788	104	32	)	)	PUNCT
eurjchem-788	104	33	,	,	PUNCT
eurjchem-788	104	34	766	766	NUM
eurjchem-788	104	35	(	(	PUNCT
eurjchem-788	104	36	disubstituted	disubstitute	VERB
eurjchem-788	104	37	phenyl	phenyl	NOUN
eurjchem-788	104	38	)	)	PUNCT
eurjchem-788	104	39	.	.	PUNCT
eurjchem-788	105	1	1h	1h	NUM
eurjchem-788	105	2	nmr	nmr	NOUN
eurjchem-788	105	3	(	(	PUNCT
eurjchem-788	105	4	300	300	NUM
eurjchem-788	105	5	mhz	mhz	NOUN
eurjchem-788	105	6	,	,	PUNCT
eurjchem-788	105	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	105	8	,	,	PUNCT
eurjchem-788	105	9	δ	δ	PROPN
eurjchem-788	105	10	,	,	PUNCT
eurjchem-788	105	11	ppm	ppm	NUM
eurjchem-788	105	12	):	):	PUNCT
eurjchem-788	105	13	7.41	7.41	NUM
eurjchem-788	105	14	(	(	PUNCT
eurjchem-788	105	15	m	m	PROPN
eurjchem-788	105	16	,	,	PUNCT
eurjchem-788	105	17	4h	4h	NUM
eurjchem-788	105	18	,	,	PUNCT
eurjchem-788	105	19	arh	arh	PROPN
eurjchem-788	105	20	)	)	PUNCT
eurjchem-788	105	21	,	,	PUNCT
eurjchem-788	105	22	6.89	6.89	NUM
eurjchem-788	105	23	(	(	PUNCT
eurjchem-788	105	24	s	s	PROPN
eurjchem-788	105	25	,	,	PUNCT
eurjchem-788	105	26	1h	1h	NUM
eurjchem-788	105	27	,	,	PUNCT
eurjchem-788	105	28	thienyl‐h	thienyl‐h	PROPN
eurjchem-788	105	29	)	)	PUNCT
eurjchem-788	105	30	,	,	PUNCT
eurjchem-788	105	31	5.17	5.17	NUM
eurjchem-788	105	32	(	(	PUNCT
eurjchem-788	105	33	s	s	PROPN
eurjchem-788	105	34	,	,	PUNCT
eurjchem-788	105	35	br	br	PROPN
eurjchem-788	105	36	,	,	PUNCT
eurjchem-788	105	37	1h	1h	NUM
eurjchem-788	105	38	,	,	PUNCT
eurjchem-788	105	39	nh2	nh2	PROPN
eurjchem-788	105	40	)	)	PUNCT
eurjchem-788	105	41	,	,	PUNCT
eurjchem-788	105	42	2.66	2.66	NUM
eurjchem-788	105	43	(	(	PUNCT
eurjchem-788	105	44	m	m	PROPN
eurjchem-788	105	45	,	,	PUNCT
eurjchem-788	105	46	3h	3h	NUM
eurjchem-788	105	47	,	,	PUNCT
eurjchem-788	105	48	n	n	CCONJ
eurjchem-788	105	49	=	=	NOUN
eurjchem-788	105	50	c‐ch3	c‐ch3	ADJ
eurjchem-788	105	51	)	)	PUNCT
eurjchem-788	105	52	,	,	PUNCT
eurjchem-788	105	53	2.52	2.52	NUM
eurjchem-788	105	54	(	(	PUNCT
eurjchem-788	105	55	m	m	PROPN
eurjchem-788	105	56	,	,	PUNCT
eurjchem-788	105	57	3h	3h	NUM
eurjchem-788	105	58	,	,	PUNCT
eurjchem-788	105	59	ch3‐co‐	ch3‐co‐	NOUN
eurjchem-788	105	60	)	)	PUNCT
eurjchem-788	105	61	,	,	PUNCT
eurjchem-788	105	62	1.68	1.68	NUM
eurjchem-788	105	63	(	(	PUNCT
eurjchem-788	105	64	s	s	PROPN
eurjchem-788	105	65	,	,	PUNCT
eurjchem-788	105	66	br	br	PROPN
eurjchem-788	105	67	,	,	PUNCT
eurjchem-788	105	68	1h	1h	NUM
eurjchem-788	105	69	,	,	PUNCT
eurjchem-788	105	70	nh2	nh2	PROPN
eurjchem-788	105	71	linked	link	VERB
eurjchem-788	105	72	h‐bonding	h‐bonde	VERB
eurjchem-788	105	73	to	to	PART
eurjchem-788	105	74	co	co	VERB
eurjchem-788	105	75	)	)	PUNCT
eurjchem-788	105	76	.	.	PUNCT
eurjchem-788	106	1	13c	13c	NOUN
eurjchem-788	106	2	nmr	nmr	NOUN
eurjchem-788	106	3	(	(	PUNCT
eurjchem-788	106	4	75	75	NUM
eurjchem-788	106	5	mhz	mhz	NOUN
eurjchem-788	106	6	,	,	PUNCT
eurjchem-788	106	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	106	8	,	,	PUNCT
eurjchem-788	106	9	δ	δ	PROPN
eurjchem-788	106	10	,	,	PUNCT
eurjchem-788	106	11	ppm	ppm	NUM
eurjchem-788	106	12	):	):	PUNCT
eurjchem-788	106	13	197.4	197.4	NUM
eurjchem-788	106	14	(	(	PUNCT
eurjchem-788	106	15	1c	1c	NOUN
eurjchem-788	106	16	,	,	PUNCT
eurjchem-788	106	17	co	co	NOUN
eurjchem-788	106	18	)	)	PUNCT
eurjchem-788	106	19	,	,	PUNCT
eurjchem-788	106	20	161.3	161.3	NUM
eurjchem-788	106	21	(	(	PUNCT
eurjchem-788	106	22	1c	1c	NOUN
eurjchem-788	106	23	,	,	PUNCT
eurjchem-788	106	24	‐s‐c	‐s‐c	ADJ
eurjchem-788	106	25	=	=	SYM
eurjchem-788	106	26	c(n)‐	c(n)‐	NOUN
eurjchem-788	106	27	)	)	PUNCT
eurjchem-788	106	28	,	,	PUNCT
eurjchem-788	106	29	158.6	158.6	NUM
eurjchem-788	106	30	(	(	PUNCT
eurjchem-788	106	31	1c	1c	NOUN
eurjchem-788	106	32	,	,	PUNCT
eurjchem-788	106	33	‐n	‐n	ADJ
eurjchem-788	106	34	=	=	NUM
eurjchem-788	106	35	c‐	c‐	NOUN
eurjchem-788	106	36	ch3	ch3	PROPN
eurjchem-788	106	37	)	)	PUNCT
eurjchem-788	106	38	,	,	PUNCT
eurjchem-788	106	39	154.7	154.7	NUM
eurjchem-788	106	40	(	(	PUNCT
eurjchem-788	106	41	1c	1c	NOUN
eurjchem-788	106	42	,	,	PUNCT
eurjchem-788	106	43	=	=	NOUN
eurjchem-788	106	44	c‐nh2	c‐nh2	PROPN
eurjchem-788	106	45	)	)	PUNCT
eurjchem-788	106	46	,	,	PUNCT
eurjchem-788	106	47	145.9	145.9	NUM
eurjchem-788	106	48	(	(	PUNCT
eurjchem-788	106	49	1c	1c	NOUN
eurjchem-788	106	50	,	,	PUNCT
eurjchem-788	106	51	‐c	‐c	NOUN
eurjchem-788	106	52	=	=	NOUN
eurjchem-788	106	53	c‐s	c‐s	NOUN
eurjchem-788	106	54	)	)	PUNCT
eurjchem-788	106	55	,	,	PUNCT
eurjchem-788	106	56	135.9	135.9	NUM
eurjchem-788	106	57	(	(	PUNCT
eurjchem-788	106	58	1c	1c	NOUN
eurjchem-788	106	59	,	,	PUNCT
eurjchem-788	106	60	c‐ar	c‐ar	NUM
eurjchem-788	106	61	)	)	PUNCT
eurjchem-788	106	62	,	,	PUNCT
eurjchem-788	106	63	135.2	135.2	NUM
eurjchem-788	106	64	(	(	PUNCT
eurjchem-788	106	65	1c	1c	NOUN
eurjchem-788	106	66	,	,	PUNCT
eurjchem-788	106	67	cl‐c‐ar	cl‐c‐ar	NOUN
eurjchem-788	106	68	)	)	PUNCT
eurjchem-788	106	69	,	,	PUNCT
eurjchem-788	106	70	134.2	134.2	NUM
eurjchem-788	106	71	(	(	PUNCT
eurjchem-788	106	72	2c	2c	NOUN
eurjchem-788	106	73	,	,	PUNCT
eurjchem-788	106	74	ch‐ar	ch‐ar	NUM
eurjchem-788	106	75	)	)	PUNCT
eurjchem-788	106	76	,	,	PUNCT
eurjchem-788	106	77	128.7	128.7	NUM
eurjchem-788	106	78	(	(	PUNCT
eurjchem-788	106	79	2c	2c	NOUN
eurjchem-788	106	80	,	,	PUNCT
eurjchem-788	106	81	ch‐ar	ch‐ar	NUM
eurjchem-788	106	82	)	)	PUNCT
eurjchem-788	106	83	,	,	PUNCT
eurjchem-788	106	84	127.2	127.2	NUM
eurjchem-788	106	85	(	(	PUNCT
eurjchem-788	106	86	1c	1c	NOUN
eurjchem-788	106	87	,	,	PUNCT
eurjchem-788	106	88	‐c	‐c	NOUN
eurjchem-788	106	89	=	=	NOUN
eurjchem-788	106	90	c‐s	c‐s	NOUN
eurjchem-788	106	91	)	)	PUNCT
eurjchem-788	106	92	,	,	PUNCT
eurjchem-788	106	93	121.4	121.4	NUM
eurjchem-788	106	94	(	(	PUNCT
eurjchem-788	106	95	1c	1c	NOUN
eurjchem-788	106	96	,	,	PUNCT
eurjchem-788	106	97	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	106	98	=	=	NOUN
eurjchem-788	106	99	c‐c‐nh2	c‐c‐nh2	PROPN
eurjchem-788	106	100	)	)	PUNCT
eurjchem-788	106	101	,	,	PUNCT
eurjchem-788	106	102	115.5	115.5	NUM
eurjchem-788	106	103	(	(	PUNCT
eurjchem-788	106	104	1c	1c	NOUN
eurjchem-788	106	105	,	,	PUNCT
eurjchem-788	106	106	pyridinyl‐c‐co	pyridinyl‐c‐co	PRON
eurjchem-788	106	107	)	)	PUNCT
eurjchem-788	106	108	,	,	PUNCT
eurjchem-788	106	109	17.1	17.1	NUM
eurjchem-788	106	110	(	(	PUNCT
eurjchem-788	106	111	1c	1c	X
eurjchem-788	106	112	,	,	PUNCT
eurjchem-788	106	113	ch3	ch3	PROPN
eurjchem-788	106	114	)	)	PUNCT
eurjchem-788	106	115	,	,	PUNCT
eurjchem-788	106	116	14.2	14.2	NUM
eurjchem-788	106	117	(	(	PUNCT
eurjchem-788	106	118	1c	1c	X
eurjchem-788	106	119	,	,	PUNCT
eurjchem-788	106	120	ch3	ch3	PROPN
eurjchem-788	106	121	)	)	PUNCT
eurjchem-788	106	122	.	.	PUNCT
eurjchem-788	107	1	anal	anal	PROPN
eurjchem-788	107	2	.	.	PUNCT
eurjchem-788	107	3	calcd	calcd	NOUN
eurjchem-788	107	4	.	.	PUNCT
eurjchem-788	108	1	for	for	SCONJ
eurjchem-788	108	2	c16h13cln2os	c16h13cln2o	NOUN
eurjchem-788	108	3	:	:	PUNCT
eurjchem-788	108	4	c	c	X
eurjchem-788	108	5	,	,	PUNCT
eurjchem-788	108	6	60.66	60.66	NUM
eurjchem-788	108	7	;	;	PUNCT
eurjchem-788	108	8	h	h	NOUN
eurjchem-788	108	9	,	,	PUNCT
eurjchem-788	108	10	4.14	4.14	NUM
eurjchem-788	108	11	;	;	PUNCT
eurjchem-788	108	12	n	n	CCONJ
eurjchem-788	108	13	,	,	PUNCT
eurjchem-788	108	14	8.85	8.85	NUM
eurjchem-788	108	15	.	.	PUNCT
eurjchem-788	108	16	found	find	VERB
eurjchem-788	108	17	:	:	PUNCT
eurjchem-788	109	1	c	c	X
eurjchem-788	109	2	,	,	PUNCT
eurjchem-788	109	3	60.61	60.61	NUM
eurjchem-788	109	4	;	;	PUNCT
eurjchem-788	109	5	h	h	X
eurjchem-788	109	6	,	,	PUNCT
eurjchem-788	109	7	4.17	4.17	NUM
eurjchem-788	109	8	;	;	PUNCT
eurjchem-788	109	9	n	n	CCONJ
eurjchem-788	109	10	,	,	PUNCT
eurjchem-788	109	11	8.91	8.91	NUM
eurjchem-788	109	12	%	%	NOUN
eurjchem-788	109	13	.	.	PUNCT
eurjchem-788	110	1	(	(	PUNCT
eurjchem-788	110	2	4‐amino‐2‐trifluoromethyl‐5,6,7,8‐tetrahydrobenzo[4,5	4‐amino‐2‐trifluoromethyl‐5,6,7,8‐tetrahydrobenzo[4,5	NUM
eurjchem-788	110	3	]	]	PUNCT
eurjchem-788	110	4	thieno[2,3‐b]pyridin‐3‐yl)thiophen‐2‐yl‐methanone	thieno[2,3‐b]pyridin‐3‐yl)thiophen‐2‐yl‐methanone	NUM
eurjchem-788	110	5	(	(	PUNCT
eurjchem-788	110	6	2e	2e	NUM
eurjchem-788	110	7	):	):	PUNCT
eurjchem-788	110	8	following	follow	VERB
eurjchem-788	110	9	the	the	DET
eurjchem-788	110	10	general	general	ADJ
eurjchem-788	110	11	method	method	NOUN
eurjchem-788	110	12	for	for	ADP
eurjchem-788	110	13	the	the	DET
eurjchem-788	110	14	friedländer	friedländer	NOUN
eurjchem-788	110	15	reaction	reaction	NOUN
eurjchem-788	110	16	,	,	PUNCT
eurjchem-788	110	17	alcl3	alcl3	PROPN
eurjchem-788	110	18	(	(	PUNCT
eurjchem-788	110	19	800	800	NUM
eurjchem-788	110	20	mg	mg	NUM
eurjchem-788	110	21	)	)	PUNCT
eurjchem-788	110	22	or	or	CCONJ
eurjchem-788	110	23	activated	activate	VERB
eurjchem-788	110	24	bentonite	bentonite	NOUN
eurjchem-788	110	25	(	(	PUNCT
eurjchem-788	110	26	1000	1000	NUM
eurjchem-788	110	27	mg	mg	NOUN
eurjchem-788	110	28	)	)	PUNCT
eurjchem-788	110	29	in	in	ADP
eurjchem-788	110	30	dry	dry	ADJ
eurjchem-788	110	31	1,2‐	1,2‐	NUM
eurjchem-788	110	32	dichloroethane	dichloroethane	NOUN
eurjchem-788	110	33	(	(	PUNCT
eurjchem-788	110	34	50	50	NUM
eurjchem-788	110	35	ml	ml	NOUN
eurjchem-788	110	36	)	)	PUNCT
eurjchem-788	110	37	was	be	AUX
eurjchem-788	110	38	reacted	react	VERB
eurjchem-788	110	39	with	with	ADP
eurjchem-788	110	40	1‐thiophen‐2‐	1‐thiophen‐2‐	PROPN
eurjchem-788	110	41	ylbutane‐1,3‐dione	ylbutane‐1,3‐dione	NUM
eurjchem-788	110	42	(	(	PUNCT
eurjchem-788	110	43	10	10	NUM
eurjchem-788	110	44	mmol	mmol	NOUN
eurjchem-788	110	45	)	)	PUNCT
eurjchem-788	110	46	and	and	CCONJ
eurjchem-788	110	47	aminothiophene	aminothiophene	VERB
eurjchem-788	110	48	1a	1a	PROPN
eurjchem-788	110	49	(	(	PUNCT
eurjchem-788	110	50	5	5	NUM
eurjchem-788	110	51	mmol	mmol	NOUN
eurjchem-788	110	52	)	)	PUNCT
eurjchem-788	110	53	.	.	PUNCT
eurjchem-788	111	1	the	the	DET
eurjchem-788	111	2	mixture	mixture	NOUN
eurjchem-788	111	3	was	be	AUX
eurjchem-788	111	4	refluxed	refluxe	VERB
eurjchem-788	111	5	for	for	ADP
eurjchem-788	111	6	24	24	NUM
eurjchem-788	111	7	h.	h.	PROPN
eurjchem-788	111	8	work‐up	work‐up	PROPN
eurjchem-788	111	9	and	and	CCONJ
eurjchem-788	111	10	chromatography	chromatography	NOUN
eurjchem-788	111	11	provided	provide	VERB
eurjchem-788	111	12	compound	compound	NOUN
eurjchem-788	111	13	2e	2e	NOUN
eurjchem-788	111	14	.	.	PUNCT
eurjchem-788	112	1	color	color	NOUN
eurjchem-788	112	2	:	:	PUNCT
eurjchem-788	112	3	yelllow‐brown	yelllow‐brown	PROPN
eurjchem-788	112	4	.	.	PUNCT
eurjchem-788	113	1	yield	yield	NOUN
eurjchem-788	113	2	:	:	PUNCT
eurjchem-788	113	3	68	68	NUM
eurjchem-788	113	4	%	%	NOUN
eurjchem-788	113	5	.	.	PUNCT
eurjchem-788	114	1	m.p	m.p	PROPN
eurjchem-788	114	2	.	.	PROPN
eurjchem-788	114	3	:	:	PUNCT
eurjchem-788	115	1	183‐185	183‐185	NUM
eurjchem-788	115	2	°	°	SYM
eurjchem-788	115	3	c	c	X
eurjchem-788	115	4	.	.	PUNCT
eurjchem-788	116	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	116	2	(	(	PUNCT
eurjchem-788	116	3	kbr	kbr	PROPN
eurjchem-788	116	4	,	,	PUNCT
eurjchem-788	116	5	ν	ν	PROPN
eurjchem-788	116	6	,	,	PUNCT
eurjchem-788	116	7	cm‐1	cm‐1	PROPN
eurjchem-788	116	8	):	):	PUNCT
eurjchem-788	116	9	3376	3376	NUM
eurjchem-788	116	10	,	,	PUNCT
eurjchem-788	116	11	3253	3253	NUM
eurjchem-788	116	12	(nh	(nh	PROPN
eurjchem-788	116	13	)	)	PUNCT
eurjchem-788	116	14	(	(	PUNCT
eurjchem-788	116	15	nh2	nh2	PROPN
eurjchem-788	116	16	)	)	PUNCT
eurjchem-788	116	17	,	,	PUNCT
eurjchem-788	116	18	1672	1672	NUM
eurjchem-788	116	19	(co	(co	NOUN
eurjchem-788	116	20	)	)	PUNCT
eurjchem-788	116	21	,	,	PUNCT
eurjchem-788	116	22	1583	1583	NUM
eurjchem-788	116	23	(nh2	(nh2	NUM
eurjchem-788	116	24	)	)	PUNCT
eurjchem-788	116	25	(	(	PUNCT
eurjchem-788	116	26	nh2	nh2	PROPN
eurjchem-788	116	27	)	)	PUNCT
eurjchem-788	116	28	.	.	PUNCT
eurjchem-788	117	1	1h	1h	NUM
eurjchem-788	117	2	nmr	nmr	NOUN
eurjchem-788	117	3	(	(	PUNCT
eurjchem-788	117	4	300	300	NUM
eurjchem-788	117	5	mhz	mhz	NOUN
eurjchem-788	117	6	,	,	PUNCT
eurjchem-788	117	7	dmso‐d6	dmso‐d6	NOUN
eurjchem-788	117	8	+	+	CCONJ
eurjchem-788	117	9	cdcl3	cdcl3	PROPN
eurjchem-788	117	10	,	,	PUNCT
eurjchem-788	117	11	δ	δ	PROPN
eurjchem-788	117	12	,	,	PUNCT
eurjchem-788	117	13	ppm	ppm	NUM
eurjchem-788	117	14	):	):	PUNCT
eurjchem-788	117	15	7.2	7.2	NUM
eurjchem-788	117	16	(	(	PUNCT
eurjchem-788	117	17	d	d	PROPN
eurjchem-788	117	18	,	,	PUNCT
eurjchem-788	117	19	j	j	PROPN
eurjchem-788	117	20	=	=	SYM
eurjchem-788	117	21	5.2	5.2	NUM
eurjchem-788	117	22	hz	hz	NOUN
eurjchem-788	117	23	,	,	PUNCT
eurjchem-788	117	24	1h	1h	NUM
eurjchem-788	117	25	,	,	PUNCT
eurjchem-788	117	26	‐	‐	ADJ
eurjchem-788	117	27	thiophene‐h	thiophene‐h	NOUN
eurjchem-788	117	28	)	)	PUNCT
eurjchem-788	117	29	,	,	PUNCT
eurjchem-788	117	30	6.8‐6.5	6.8‐6.5	NUM
eurjchem-788	117	31	(	(	PUNCT
eurjchem-788	117	32	m	m	PROPN
eurjchem-788	117	33	,	,	PUNCT
eurjchem-788	117	34	2h	2h	NUM
eurjchem-788	117	35	,	,	PUNCT
eurjchem-788	117	36	‐thienyl‐h	‐thienyl‐h	NOUN
eurjchem-788	117	37	)	)	PUNCT
eurjchem-788	117	38	,	,	PUNCT
eurjchem-788	117	39	5.82	5.82	NUM
eurjchem-788	117	40	(	(	PUNCT
eurjchem-788	117	41	s	s	PROPN
eurjchem-788	117	42	,	,	PUNCT
eurjchem-788	117	43	br	br	PROPN
eurjchem-788	117	44	,	,	PUNCT
eurjchem-788	117	45	1h	1h	NUM
eurjchem-788	117	46	,	,	PUNCT
eurjchem-788	117	47	nh2	nh2	PROPN
eurjchem-788	117	48	)	)	PUNCT
eurjchem-788	117	49	,	,	PUNCT
eurjchem-788	117	50	2.83	2.83	NUM
eurjchem-788	117	51	(	(	PUNCT
eurjchem-788	117	52	m	m	PROPN
eurjchem-788	117	53	,	,	PUNCT
eurjchem-788	117	54	2h	2h	NUM
eurjchem-788	117	55	,	,	PUNCT
eurjchem-788	117	56	‐ch2	‐ch2	NUM
eurjchem-788	117	57	)	)	PUNCT
eurjchem-788	117	58	,	,	PUNCT
eurjchem-788	117	59	2.58	2.58	NUM
eurjchem-788	117	60	(	(	PUNCT
eurjchem-788	117	61	m	m	PROPN
eurjchem-788	117	62	,	,	PUNCT
eurjchem-788	117	63	2h	2h	NUM
eurjchem-788	117	64	,	,	PUNCT
eurjchem-788	117	65	‐ch2	‐ch2	NUM
eurjchem-788	117	66	)	)	PUNCT
eurjchem-788	117	67	,	,	PUNCT
eurjchem-788	117	68	2.08	2.08	NUM
eurjchem-788	117	69	(	(	PUNCT
eurjchem-788	117	70	m	m	PROPN
eurjchem-788	117	71	,	,	PUNCT
eurjchem-788	117	72	4h	4h	NUM
eurjchem-788	117	73	,	,	PUNCT
eurjchem-788	117	74	2*‐ch2	2*‐ch2	NUM
eurjchem-788	117	75	)	)	PUNCT
eurjchem-788	117	76	,	,	PUNCT
eurjchem-788	117	77	1.72	1.72	NUM
eurjchem-788	117	78	(	(	PUNCT
eurjchem-788	117	79	s	s	PROPN
eurjchem-788	117	80	,	,	PUNCT
eurjchem-788	117	81	br	br	PROPN
eurjchem-788	117	82	,	,	PUNCT
eurjchem-788	117	83	1h	1h	NUM
eurjchem-788	117	84	,	,	PUNCT
eurjchem-788	117	85	nh2	nh2	PROPN
eurjchem-788	117	86	linked	link	VERB
eurjchem-788	117	87	h‐bonding	h‐bonde	VERB
eurjchem-788	117	88	to	to	PART
eurjchem-788	117	89	co	co	VERB
eurjchem-788	117	90	)	)	PUNCT
eurjchem-788	117	91	.	.	PUNCT
eurjchem-788	118	1	13c	13c	NOUN
eurjchem-788	118	2	nmr	nmr	NOUN
eurjchem-788	118	3	(	(	PUNCT
eurjchem-788	118	4	75	75	NUM
eurjchem-788	118	5	mhz	mhz	NOUN
eurjchem-788	118	6	,	,	PUNCT
eurjchem-788	118	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	118	8	,	,	PUNCT
eurjchem-788	118	9	δ	δ	PROPN
eurjchem-788	118	10	,	,	PUNCT
eurjchem-788	118	11	ppm	ppm	NUM
eurjchem-788	118	12	):	):	PUNCT
eurjchem-788	118	13	196.5	196.5	NUM
eurjchem-788	118	14	(	(	PUNCT
eurjchem-788	118	15	1c	1c	NOUN
eurjchem-788	118	16	,	,	PUNCT
eurjchem-788	118	17	co	co	NOUN
eurjchem-788	118	18	)	)	PUNCT
eurjchem-788	118	19	,	,	PUNCT
eurjchem-788	118	20	163.7	163.7	NUM
eurjchem-788	118	21	(	(	PUNCT
eurjchem-788	118	22	1c	1c	NOUN
eurjchem-788	118	23	,	,	PUNCT
eurjchem-788	118	24	‐s‐c	‐s‐c	ADJ
eurjchem-788	118	25	=	=	SYM
eurjchem-788	118	26	c(n)‐	c(n)‐	NOUN
eurjchem-788	118	27	)	)	PUNCT
eurjchem-788	118	28	,	,	PUNCT
eurjchem-788	118	29	159.2	159.2	NUM
eurjchem-788	118	30	(	(	PUNCT
eurjchem-788	118	31	1c	1c	NOUN
eurjchem-788	118	32	,	,	PUNCT
eurjchem-788	118	33	‐n	‐n	ADJ
eurjchem-788	118	34	=	=	ADJ
eurjchem-788	118	35	c‐cf3	c‐cf3	PROPN
eurjchem-788	118	36	)	)	PUNCT
eurjchem-788	118	37	,	,	PUNCT
eurjchem-788	118	38	151.7	151.7	NUM
eurjchem-788	118	39	(	(	PUNCT
eurjchem-788	118	40	1c	1c	X
eurjchem-788	118	41	,	,	PUNCT
eurjchem-788	118	42	=	=	NOUN
eurjchem-788	118	43	c‐nh2	c‐nh2	PROPN
eurjchem-788	118	44	)	)	PUNCT
eurjchem-788	118	45	,	,	PUNCT
eurjchem-788	118	46	146.8	146.8	NUM
eurjchem-788	118	47	(	(	PUNCT
eurjchem-788	118	48	1c	1c	NOUN
eurjchem-788	118	49	,	,	PUNCT
eurjchem-788	118	50	‐c	‐c	NOUN
eurjchem-788	118	51	=	=	NOUN
eurjchem-788	118	52	c‐s	c‐s	NOUN
eurjchem-788	118	53	)	)	PUNCT
eurjchem-788	118	54	,	,	PUNCT
eurjchem-788	118	55	136.2	136.2	NUM
eurjchem-788	118	56	,	,	PUNCT
eurjchem-788	118	57	(	(	PUNCT
eurjchem-788	118	58	1c	1c	X
eurjchem-788	118	59	,	,	PUNCT
eurjchem-788	118	60	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	118	61	)	)	PUNCT
eurjchem-788	118	62	,	,	PUNCT
eurjchem-788	118	63	131.2	131.2	NUM
eurjchem-788	118	64	(	(	PUNCT
eurjchem-788	118	65	1c	1c	NOUN
eurjchem-788	118	66	,	,	PUNCT
eurjchem-788	118	67	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	118	68	)	)	PUNCT
eurjchem-788	118	69	,	,	PUNCT
eurjchem-788	118	70	130.1	130.1	NUM
eurjchem-788	118	71	(	(	PUNCT
eurjchem-788	118	72	1c	1c	NOUN
eurjchem-788	118	73	,	,	PUNCT
eurjchem-788	118	74	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	118	75	)	)	PUNCT
eurjchem-788	118	76	,	,	PUNCT
eurjchem-788	118	77	128.5	128.5	NUM
eurjchem-788	118	78	(	(	PUNCT
eurjchem-788	118	79	1c	1c	NOUN
eurjchem-788	118	80	,	,	PUNCT
eurjchem-788	118	81	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	118	82	)	)	PUNCT
eurjchem-788	118	83	,	,	PUNCT
eurjchem-788	118	84	126.3	126.3	NUM
eurjchem-788	118	85	(	(	PUNCT
eurjchem-788	118	86	1c	1c	NOUN
eurjchem-788	118	87	,	,	PUNCT
eurjchem-788	118	88	‐c	‐c	NOUN
eurjchem-788	118	89	=	=	NOUN
eurjchem-788	118	90	c‐s	c‐s	NOUN
eurjchem-788	118	91	)	)	PUNCT
eurjchem-788	118	92	,	,	PUNCT
eurjchem-788	118	93	125.7	125.7	NUM
eurjchem-788	118	94	(	(	PUNCT
eurjchem-788	118	95	1c	1c	NUM
eurjchem-788	118	96	,	,	PUNCT
eurjchem-788	118	97	thienyl‐	thienyl‐	NOUN
eurjchem-788	118	98	c	c	NOUN
eurjchem-788	118	99	=	=	NOUN
eurjchem-788	118	100	c‐c‐nh2	c‐c‐nh2	PROPN
eurjchem-788	118	101	)	)	PUNCT
eurjchem-788	118	102	,	,	PUNCT
eurjchem-788	118	103	118.2	118.2	NUM
eurjchem-788	118	104	(	(	PUNCT
eurjchem-788	118	105	1c	1c	NOUN
eurjchem-788	118	106	,	,	PUNCT
eurjchem-788	118	107	pyridinyl‐c‐co	pyridinyl‐c‐co	PRON
eurjchem-788	118	108	)	)	PUNCT
eurjchem-788	118	109	,	,	PUNCT
eurjchem-788	118	110	114.2	114.2	NUM
eurjchem-788	118	111	(	(	PUNCT
eurjchem-788	118	112	1c	1c	NOUN
eurjchem-788	118	113	,	,	PUNCT
eurjchem-788	118	114	cf3	cf3	PROPN
eurjchem-788	118	115	)	)	PUNCT
eurjchem-788	118	116	,	,	PUNCT
eurjchem-788	118	117	28.3	28.3	NUM
eurjchem-788	118	118	(	(	PUNCT
eurjchem-788	118	119	1c	1c	NOUN
eurjchem-788	118	120	,	,	PUNCT
eurjchem-788	118	121	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	118	122	)	)	PUNCT
eurjchem-788	118	123	,	,	PUNCT
eurjchem-788	118	124	28.1	28.1	NUM
eurjchem-788	118	125	(	(	PUNCT
eurjchem-788	118	126	1c	1c	NOUN
eurjchem-788	118	127	,	,	PUNCT
eurjchem-788	118	128	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	118	129	)	)	PUNCT
eurjchem-788	118	130	,	,	PUNCT
eurjchem-788	118	131	25.3	25.3	NUM
eurjchem-788	118	132	(	(	PUNCT
eurjchem-788	118	133	1c	1c	NOUN
eurjchem-788	118	134	,	,	PUNCT
eurjchem-788	118	135	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	118	136	)	)	PUNCT
eurjchem-788	118	137	,	,	PUNCT
eurjchem-788	118	138	24.8	24.8	NUM
eurjchem-788	118	139	(	(	PUNCT
eurjchem-788	118	140	1c	1c	NOUN
eurjchem-788	118	141	,	,	PUNCT
eurjchem-788	118	142	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	118	143	)	)	PUNCT
eurjchem-788	118	144	.	.	PUNCT
eurjchem-788	119	1	anal	anal	PROPN
eurjchem-788	119	2	.	.	PUNCT
eurjchem-788	119	3	calcd	calcd	NOUN
eurjchem-788	119	4	.	.	PUNCT
eurjchem-788	120	1	for	for	ADP
eurjchem-788	120	2	c17h13f3n2os	c17h13f3n2os	PROPN
eurjchem-788	120	3	:	:	PUNCT
eurjchem-788	120	4	c	c	X
eurjchem-788	120	5	,	,	PUNCT
eurjchem-788	120	6	58.28	58.28	NUM
eurjchem-788	120	7	;	;	PUNCT
eurjchem-788	120	8	h	h	NOUN
eurjchem-788	120	9	,	,	PUNCT
eurjchem-788	120	10	3.74	3.74	NUM
eurjchem-788	120	11	;	;	PUNCT
eurjchem-788	120	12	n	n	CCONJ
eurjchem-788	120	13	,	,	PUNCT
eurjchem-788	120	14	8.00	8.00	NUM
eurjchem-788	120	15	.	.	PUNCT
eurjchem-788	120	16	found	find	VERB
eurjchem-788	120	17	:	:	PUNCT
eurjchem-788	121	1	c	c	X
eurjchem-788	121	2	,	,	PUNCT
eurjchem-788	121	3	58.19	58.19	NUM
eurjchem-788	121	4	;	;	PUNCT
eurjchem-788	121	5	h	h	NOUN
eurjchem-788	121	6	,	,	PUNCT
eurjchem-788	121	7	3.82	3.82	NUM
eurjchem-788	121	8	;	;	PUNCT
eurjchem-788	121	9	n	n	CCONJ
eurjchem-788	121	10	,	,	PUNCT
eurjchem-788	121	11	8.07	8.07	NUM
eurjchem-788	121	12	%	%	NOUN
eurjchem-788	121	13	.	.	PUNCT
eurjchem-788	122	1	11‐amino‐1,2,3,4,7,8,9,10‐octahydro[1]benzothieno[2,3‐b	11‐amino‐1,2,3,4,7,8,9,10‐octahydro[1]benzothieno[2,3‐b	NUM
eurjchem-788	122	2	]	]	X
eurjchem-788	122	3	quinoline	quinoline	NOUN
eurjchem-788	122	4	(	(	PUNCT
eurjchem-788	122	5	3a	3a	NUM
eurjchem-788	122	6	):	):	PUNCT
eurjchem-788	122	7	following	follow	VERB
eurjchem-788	122	8	the	the	DET
eurjchem-788	122	9	general	general	ADJ
eurjchem-788	122	10	method	method	NOUN
eurjchem-788	122	11	for	for	ADP
eurjchem-788	122	12	the	the	DET
eurjchem-788	122	13	friedländer	friedländer	NOUN
eurjchem-788	122	14	reaction	reaction	NOUN
eurjchem-788	122	15	,	,	PUNCT
eurjchem-788	122	16	alcl3	alcl3	PROPN
eurjchem-788	122	17	(	(	PUNCT
eurjchem-788	122	18	800	800	NUM
eurjchem-788	122	19	mg	mg	NUM
eurjchem-788	122	20	)	)	PUNCT
eurjchem-788	122	21	or	or	CCONJ
eurjchem-788	122	22	activated	activate	VERB
eurjchem-788	122	23	bentonite	bentonite	NOUN
eurjchem-788	122	24	(	(	PUNCT
eurjchem-788	122	25	1000	1000	NUM
eurjchem-788	122	26	mg	mg	NOUN
eurjchem-788	122	27	)	)	PUNCT
eurjchem-788	122	28	in	in	ADP
eurjchem-788	122	29	dry	dry	ADJ
eurjchem-788	122	30	1,2‐dichloroethane	1,2‐dichloroethane	NOUN
eurjchem-788	122	31	(	(	PUNCT
eurjchem-788	122	32	50	50	NUM
eurjchem-788	122	33	ml	ml	NOUN
eurjchem-788	122	34	)	)	PUNCT
eurjchem-788	122	35	was	be	AUX
eurjchem-788	122	36	reacted	react	VERB
eurjchem-788	122	37	with	with	ADP
eurjchem-788	122	38	cyclohexanone	cyclohexanone	PROPN
eurjchem-788	122	39	(	(	PUNCT
eurjchem-788	122	40	10	10	NUM
eurjchem-788	122	41	mmol	mmol	NOUN
eurjchem-788	122	42	)	)	PUNCT
eurjchem-788	122	43	and	and	CCONJ
eurjchem-788	122	44	aminothiophene	aminothiophene	VERB
eurjchem-788	122	45	1a	1a	PROPN
eurjchem-788	122	46	(	(	PUNCT
eurjchem-788	122	47	5	5	NUM
eurjchem-788	122	48	mmol	mmol	NOUN
eurjchem-788	122	49	)	)	PUNCT
eurjchem-788	122	50	.	.	PUNCT
eurjchem-788	123	1	the	the	DET
eurjchem-788	123	2	mixture	mixture	NOUN
eurjchem-788	123	3	was	be	AUX
eurjchem-788	123	4	refluxed	refluxe	VERB
eurjchem-788	123	5	for	for	ADP
eurjchem-788	123	6	24	24	NUM
eurjchem-788	123	7	h.	h.	PROPN
eurjchem-788	123	8	work‐up	work‐up	PROPN
eurjchem-788	123	9	and	and	CCONJ
eurjchem-788	123	10	chromatography	chromatography	NOUN
eurjchem-788	123	11	provided	provide	VERB
eurjchem-788	123	12	compound	compound	NOUN
eurjchem-788	123	13	3a	3a	NUM
eurjchem-788	123	14	.	.	PUNCT
eurjchem-788	124	1	color	color	NOUN
eurjchem-788	124	2	:	:	PUNCT
eurjchem-788	124	3	brown	brown	ADJ
eurjchem-788	124	4	.	.	PUNCT
eurjchem-788	125	1	yield	yield	NOUN
eurjchem-788	125	2	:	:	PUNCT
eurjchem-788	125	3	93	93	NUM
eurjchem-788	125	4	%	%	NOUN
eurjchem-788	125	5	.	.	PUNCT
eurjchem-788	126	1	m.p	m.p	PROPN
eurjchem-788	126	2	.	.	PROPN
eurjchem-788	126	3	:	:	PUNCT
eurjchem-788	127	1	215‐217	215‐217	NUM
eurjchem-788	127	2	°	°	PROPN
eurjchem-788	127	3	c	c	NOUN
eurjchem-788	127	4	.	.	PUNCT
eurjchem-788	128	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	128	2	(	(	PUNCT
eurjchem-788	128	3	kbr	kbr	PROPN
eurjchem-788	128	4	,	,	PUNCT
eurjchem-788	128	5	ν	ν	PROPN
eurjchem-788	128	6	,	,	PUNCT
eurjchem-788	128	7	cm‐1	cm‐1	PROPN
eurjchem-788	128	8	):	):	PUNCT
eurjchem-788	128	9	3471	3471	NUM
eurjchem-788	128	10	,	,	PUNCT
eurjchem-788	128	11	3356	3356	NUM
eurjchem-788	128	12	(nh	(nh	PROPN
eurjchem-788	128	13	)	)	PUNCT
eurjchem-788	128	14	(	(	PUNCT
eurjchem-788	128	15	nh2	nh2	PROPN
eurjchem-788	128	16	)	)	PUNCT
eurjchem-788	128	17	,	,	PUNCT
eurjchem-788	128	18	1602	1602	NUM
eurjchem-788	128	19	(nh	(nh	PROPN
eurjchem-788	128	20	)	)	PUNCT
eurjchem-788	128	21	(	(	PUNCT
eurjchem-788	128	22	nh2	nh2	PROPN
eurjchem-788	128	23	)	)	PUNCT
eurjchem-788	128	24	,	,	PUNCT
eurjchem-788	128	25	1431	1431	NUM
eurjchem-788	128	26	(	(	PUNCT
eurjchem-788	128	27	ch2	ch2	PROPN
eurjchem-788	128	28	)	)	PUNCT
eurjchem-788	128	29	.	.	PUNCT
eurjchem-788	129	1	1h	1h	NUM
eurjchem-788	129	2	nmr	nmr	NOUN
eurjchem-788	129	3	(	(	PUNCT
eurjchem-788	129	4	300	300	NUM
eurjchem-788	129	5	mhz	mhz	NOUN
eurjchem-788	129	6	,	,	PUNCT
eurjchem-788	129	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	129	8	,	,	PUNCT
eurjchem-788	129	9	δ	δ	PROPN
eurjchem-788	129	10	,	,	PUNCT
eurjchem-788	129	11	ppm	ppm	NUM
eurjchem-788	129	12	):	):	PUNCT
eurjchem-788	129	13	4.62	4.62	NUM
eurjchem-788	129	14	(	(	PUNCT
eurjchem-788	129	15	s	s	PROPN
eurjchem-788	129	16	,	,	PUNCT
eurjchem-788	129	17	br	br	PROPN
eurjchem-788	129	18	,	,	PUNCT
eurjchem-788	129	19	2h	2h	NUM
eurjchem-788	129	20	,	,	PUNCT
eurjchem-788	129	21	nh2	nh2	PROPN
eurjchem-788	129	22	)	)	PUNCT
eurjchem-788	129	23	,	,	PUNCT
eurjchem-788	129	24	2.93	2.93	NUM
eurjchem-788	129	25	(	(	PUNCT
eurjchem-788	129	26	m	m	PROPN
eurjchem-788	129	27	,	,	PUNCT
eurjchem-788	129	28	2h	2h	NUM
eurjchem-788	129	29	,	,	PUNCT
eurjchem-788	129	30	ch2	ch2	PROPN
eurjchem-788	129	31	)	)	PUNCT
eurjchem-788	129	32	,	,	PUNCT
eurjchem-788	129	33	2.81	2.81	NUM
eurjchem-788	129	34	(	(	PUNCT
eurjchem-788	129	35	m	m	PROPN
eurjchem-788	129	36	,	,	PUNCT
eurjchem-788	129	37	2h	2h	NUM
eurjchem-788	129	38	,	,	PUNCT
eurjchem-788	129	39	ch2	ch2	PROPN
eurjchem-788	129	40	)	)	PUNCT
eurjchem-788	129	41	,	,	PUNCT
eurjchem-788	129	42	2.51	2.51	NUM
eurjchem-788	129	43	(	(	PUNCT
eurjchem-788	129	44	m	m	PROPN
eurjchem-788	129	45	,	,	PUNCT
eurjchem-788	129	46	4h	4h	NOUN
eurjchem-788	129	47	,	,	PUNCT
eurjchem-788	129	48	2*ch2	2*ch2	NUM
eurjchem-788	129	49	)	)	PUNCT
eurjchem-788	129	50	,	,	PUNCT
eurjchem-788	129	51	1.96‐1.91	1.96‐1.91	NUM
eurjchem-788	129	52	(	(	PUNCT
eurjchem-788	129	53	m	m	PROPN
eurjchem-788	129	54	,	,	PUNCT
eurjchem-788	129	55	8h	8h	NUM
eurjchem-788	129	56	,	,	PUNCT
eurjchem-788	129	57	4*ch2	4*ch2	NUM
eurjchem-788	129	58	)	)	PUNCT
eurjchem-788	129	59	.	.	PUNCT
eurjchem-788	130	1	13c	13c	NOUN
eurjchem-788	130	2	nmr	nmr	NOUN
eurjchem-788	130	3	(	(	PUNCT
eurjchem-788	130	4	75	75	NUM
eurjchem-788	130	5	mhz	mhz	NOUN
eurjchem-788	130	6	,	,	PUNCT
eurjchem-788	130	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	130	8	,	,	PUNCT
eurjchem-788	130	9	δ	δ	PROPN
eurjchem-788	130	10	,	,	PUNCT
eurjchem-788	130	11	ppm	ppm	NUM
eurjchem-788	130	12	):	):	PUNCT
eurjchem-788	130	13	159.1	159.1	NUM
eurjchem-788	130	14	(	(	PUNCT
eurjchem-788	130	15	1c	1c	NOUN
eurjchem-788	130	16	,	,	PUNCT
eurjchem-788	130	17	‐s‐c	‐s‐c	ADJ
eurjchem-788	130	18	=	=	SYM
eurjchem-788	130	19	c(n)‐	c(n)‐	NOUN
eurjchem-788	130	20	)	)	PUNCT
eurjchem-788	130	21	,	,	PUNCT
eurjchem-788	130	22	153.9	153.9	NUM
eurjchem-788	130	23	(	(	PUNCT
eurjchem-788	130	24	1c	1c	NOUN
eurjchem-788	130	25	,	,	PUNCT
eurjchem-788	130	26	‐n	‐n	ADJ
eurjchem-788	130	27	=	=	NOUN
eurjchem-788	130	28	c‐ch2‐	c‐ch2‐	PROPN
eurjchem-788	130	29	)	)	PUNCT
eurjchem-788	130	30	,	,	PUNCT
eurjchem-788	130	31	147.7	147.7	NUM
eurjchem-788	130	32	(	(	PUNCT
eurjchem-788	130	33	1c	1c	NOUN
eurjchem-788	130	34	,	,	PUNCT
eurjchem-788	130	35	=	=	NOUN
eurjchem-788	130	36	c‐nh2	c‐nh2	PROPN
eurjchem-788	130	37	)	)	PUNCT
eurjchem-788	130	38	,	,	PUNCT
eurjchem-788	130	39	132.8	132.8	NUM
eurjchem-788	130	40	(	(	PUNCT
eurjchem-788	130	41	1c	1c	NOUN
eurjchem-788	130	42	,	,	PUNCT
eurjchem-788	130	43	‐c	‐c	NOUN
eurjchem-788	130	44	=	=	NOUN
eurjchem-788	130	45	c‐s	c‐s	NOUN
eurjchem-788	130	46	)	)	PUNCT
eurjchem-788	130	47	,	,	PUNCT
eurjchem-788	130	48	131.6	131.6	NUM
eurjchem-788	130	49	(	(	PUNCT
eurjchem-788	130	50	1c	1c	NOUN
eurjchem-788	130	51	,	,	PUNCT
eurjchem-788	130	52	‐c	‐c	NOUN
eurjchem-788	130	53	=	=	NOUN
eurjchem-788	130	54	c‐s	c‐s	NOUN
eurjchem-788	130	55	)	)	PUNCT
eurjchem-788	130	56	,	,	PUNCT
eurjchem-788	130	57	126.1	126.1	NUM
eurjchem-788	130	58	(	(	PUNCT
eurjchem-788	130	59	1c	1c	NOUN
eurjchem-788	130	60	,	,	PUNCT
eurjchem-788	130	61	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	130	62	=	=	NOUN
eurjchem-788	130	63	c‐c‐nh2	c‐c‐nh2	PROPN
eurjchem-788	130	64	)	)	PUNCT
eurjchem-788	130	65	,	,	PUNCT
eurjchem-788	130	66	117.3	117.3	NUM
eurjchem-788	130	67	(	(	PUNCT
eurjchem-788	130	68	1c	1c	NOUN
eurjchem-788	130	69	,	,	PUNCT
eurjchem-788	130	70	pyridinyl‐c‐ch2	pyridinyl‐c‐ch2	NOUN
eurjchem-788	130	71	)	)	PUNCT
eurjchem-788	130	72	,	,	PUNCT
eurjchem-788	130	73	43.7	43.7	NUM
eurjchem-788	130	74	(	(	PUNCT
eurjchem-788	130	75	1c	1c	NOUN
eurjchem-788	130	76	,	,	PUNCT
eurjchem-788	130	77	thienyl‐ch2‐ch2‐ch2‐ch2‐	thienyl‐ch2‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	130	78	)	)	PUNCT
eurjchem-788	130	79	,	,	PUNCT
eurjchem-788	130	80	42.6	42.6	NUM
eurjchem-788	130	81	(	(	PUNCT
eurjchem-788	130	82	1c	1c	NOUN
eurjchem-788	130	83	,	,	PUNCT
eurjchem-788	130	84	thienyl‐ch2‐ch2‐ch2‐ch2‐	thienyl‐ch2‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	130	85	)	)	PUNCT
eurjchem-788	130	86	,	,	PUNCT
eurjchem-788	130	87	33.3	33.3	NUM
eurjchem-788	130	88	(	(	PUNCT
eurjchem-788	130	89	1c	1c	NOUN
eurjchem-788	130	90	,	,	PUNCT
eurjchem-788	130	91	pyridinyl‐ch2‐ch2‐	pyridinyl‐ch2‐ch2‐	PROPN
eurjchem-788	130	92	ch2‐ch2‐	ch2‐ch2‐	NOUN
eurjchem-788	130	93	)	)	PUNCT
eurjchem-788	130	94	,	,	PUNCT
eurjchem-788	130	95	31.0	31.0	NUM
eurjchem-788	130	96	(	(	PUNCT
eurjchem-788	130	97	1c	1c	NOUN
eurjchem-788	130	98	,	,	PUNCT
eurjchem-788	130	99	pyridinyl‐ch2‐ch2‐ch2‐ch2‐	pyridinyl‐ch2‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	130	100	)	)	PUNCT
eurjchem-788	130	101	,	,	PUNCT
eurjchem-788	130	102	25.7	25.7	NUM
eurjchem-788	130	103	(	(	PUNCT
eurjchem-788	130	104	1c	1c	NOUN
eurjchem-788	130	105	,	,	PUNCT
eurjchem-788	130	106	pyridinyl‐ch2‐ch2‐ch2‐ch2‐	pyridinyl‐ch2‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	130	107	)	)	PUNCT
eurjchem-788	130	108	,	,	PUNCT
eurjchem-788	130	109	23.4	23.4	NUM
eurjchem-788	130	110	(	(	PUNCT
eurjchem-788	130	111	1c	1c	NOUN
eurjchem-788	130	112	,	,	PUNCT
eurjchem-788	130	113	thienyl‐ch2‐ch2‐ch2‐	thienyl‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	130	114	ch2‐	ch2‐	NOUN
eurjchem-788	130	115	)	)	PUNCT
eurjchem-788	130	116	,	,	PUNCT
eurjchem-788	130	117	22.6	22.6	NUM
eurjchem-788	130	118	(	(	PUNCT
eurjchem-788	130	119	1c	1c	NOUN
eurjchem-788	130	120	,	,	PUNCT
eurjchem-788	130	121	thienyl‐ch2‐ch2‐ch2‐ch2‐	thienyl‐ch2‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	130	122	)	)	PUNCT
eurjchem-788	130	123	,	,	PUNCT
eurjchem-788	130	124	21.9	21.9	NUM
eurjchem-788	130	125	(	(	PUNCT
eurjchem-788	130	126	1c	1c	NOUN
eurjchem-788	130	127	,	,	PUNCT
eurjchem-788	130	128	pyridinyl‐	pyridinyl‐	NOUN
eurjchem-788	130	129	ch2‐ch2‐ch2‐ch2‐	ch2‐ch2‐ch2‐ch2‐	NOUN
eurjchem-788	130	130	)	)	PUNCT
eurjchem-788	130	131	.	.	PUNCT
eurjchem-788	131	1	anal	anal	PROPN
eurjchem-788	131	2	.	.	PUNCT
eurjchem-788	131	3	calcd	calcd	NOUN
eurjchem-788	131	4	.	.	PUNCT
eurjchem-788	132	1	for	for	ADP
eurjchem-788	132	2	c15h18n2s	c15h18n2s	NOUN
eurjchem-788	132	3	:	:	PUNCT
eurjchem-788	132	4	c	c	X
eurjchem-788	132	5	,	,	PUNCT
eurjchem-788	132	6	69.71	69.71	NUM
eurjchem-788	132	7	;	;	PUNCT
eurjchem-788	132	8	h	h	NOUN
eurjchem-788	132	9	,	,	PUNCT
eurjchem-788	132	10	7.02	7.02	NUM
eurjchem-788	132	11	;	;	PUNCT
eurjchem-788	132	12	n	n	CCONJ
eurjchem-788	132	13	,	,	PUNCT
eurjchem-788	132	14	10.83	10.83	NUM
eurjchem-788	132	15	.	.	PUNCT
eurjchem-788	132	16	found	find	VERB
eurjchem-788	132	17	:	:	PUNCT
eurjchem-788	133	1	c	c	X
eurjchem-788	133	2	,	,	PUNCT
eurjchem-788	133	3	69.52	69.52	NUM
eurjchem-788	133	4	;	;	PUNCT
eurjchem-788	134	1	h	h	NOUN
eurjchem-788	134	2	,	,	PUNCT
eurjchem-788	134	3	7.08	7.08	NUM
eurjchem-788	134	4	;	;	PUNCT
eurjchem-788	134	5	n	n	CCONJ
eurjchem-788	134	6	,	,	PUNCT
eurjchem-788	134	7	10.91	10.91	NUM
eurjchem-788	134	8	%	%	NOUN
eurjchem-788	134	9	.	.	PUNCT
eurjchem-788	135	1	2,3‐dimethyl‐5,6,7,8‐tetrahydrothieno[2,3‐b]quinolin‐4‐	2,3‐dimethyl‐5,6,7,8‐tetrahydrothieno[2,3‐b]quinolin‐4‐	NUM
eurjchem-788	135	2	amine	amine	NOUN
eurjchem-788	135	3	(	(	PUNCT
eurjchem-788	135	4	3b	3b	NUM
eurjchem-788	135	5	):	):	PUNCT
eurjchem-788	135	6	following	follow	VERB
eurjchem-788	135	7	the	the	DET
eurjchem-788	135	8	general	general	ADJ
eurjchem-788	135	9	method	method	NOUN
eurjchem-788	135	10	for	for	ADP
eurjchem-788	135	11	the	the	DET
eurjchem-788	135	12	friedländer	friedländer	NOUN
eurjchem-788	135	13	reaction	reaction	NOUN
eurjchem-788	135	14	,	,	PUNCT
eurjchem-788	135	15	alcl3	alcl3	PROPN
eurjchem-788	135	16	(	(	PUNCT
eurjchem-788	135	17	800	800	NUM
eurjchem-788	135	18	mg	mg	NUM
eurjchem-788	135	19	)	)	PUNCT
eurjchem-788	135	20	or	or	CCONJ
eurjchem-788	135	21	activated	activate	VERB
eurjchem-788	135	22	bentonite	bentonite	NOUN
eurjchem-788	135	23	(	(	PUNCT
eurjchem-788	135	24	1000	1000	NUM
eurjchem-788	135	25	mg	mg	NOUN
eurjchem-788	135	26	)	)	PUNCT
eurjchem-788	135	27	in	in	ADP
eurjchem-788	135	28	dry	dry	ADJ
eurjchem-788	135	29	1,2‐dichloroethane	1,2‐dichloroethane	NOUN
eurjchem-788	135	30	(	(	PUNCT
eurjchem-788	135	31	50	50	NUM
eurjchem-788	135	32	ml	ml	NOUN
eurjchem-788	135	33	)	)	PUNCT
eurjchem-788	135	34	was	be	AUX
eurjchem-788	135	35	reacted	react	VERB
eurjchem-788	135	36	with	with	ADP
eurjchem-788	135	37	cyclohexanone	cyclohexanone	PROPN
eurjchem-788	135	38	(	(	PUNCT
eurjchem-788	135	39	10	10	NUM
eurjchem-788	135	40	mmol	mmol	NOUN
eurjchem-788	135	41	)	)	PUNCT
eurjchem-788	135	42	and	and	CCONJ
eurjchem-788	135	43	aminothiophene	aminothiophene	VERB
eurjchem-788	135	44	1b	1b	NUM
eurjchem-788	135	45	(	(	PUNCT
eurjchem-788	135	46	5	5	NUM
eurjchem-788	135	47	mmol	mmol	NOUN
eurjchem-788	135	48	)	)	PUNCT
eurjchem-788	135	49	.	.	PUNCT
eurjchem-788	136	1	the	the	DET
eurjchem-788	136	2	mixture	mixture	NOUN
eurjchem-788	136	3	was	be	AUX
eurjchem-788	136	4	refluxed	refluxe	VERB
eurjchem-788	136	5	for	for	ADP
eurjchem-788	136	6	24	24	NUM
eurjchem-788	136	7	h.	h.	PROPN
eurjchem-788	136	8	work‐up	work‐up	PROPN
eurjchem-788	136	9	and	and	CCONJ
eurjchem-788	136	10	chromatography	chromatography	NOUN
eurjchem-788	136	11	provided	provide	VERB
eurjchem-788	136	12	compound	compound	NOUN
eurjchem-788	136	13	3b	3b	NOUN
eurjchem-788	136	14	.	.	PUNCT
eurjchem-788	137	1	color	color	NOUN
eurjchem-788	137	2	:	:	PUNCT
eurjchem-788	137	3	grey	grey	PROPN
eurjchem-788	137	4	.	.	PUNCT
eurjchem-788	138	1	yield	yield	NOUN
eurjchem-788	138	2	:	:	PUNCT
eurjchem-788	138	3	88	88	NUM
eurjchem-788	138	4	%	%	NOUN
eurjchem-788	138	5	.	.	PUNCT
eurjchem-788	139	1	m.p	m.p	PROPN
eurjchem-788	139	2	.	.	PROPN
eurjchem-788	139	3	:	:	PUNCT
eurjchem-788	140	1	166‐168	166‐168	NUM
eurjchem-788	140	2	°	°	ADP
eurjchem-788	140	3	c	c	NOUN
eurjchem-788	140	4	.	.	PUNCT
eurjchem-788	141	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	141	2	(	(	PUNCT
eurjchem-788	141	3	kbr	kbr	PROPN
eurjchem-788	141	4	,	,	PUNCT
eurjchem-788	141	5	ν	ν	PROPN
eurjchem-788	141	6	,	,	PUNCT
eurjchem-788	141	7	cm‐1	cm‐1	PROPN
eurjchem-788	141	8	):	):	PUNCT
eurjchem-788	141	9	3496	3496	NUM
eurjchem-788	141	10	,	,	PUNCT
eurjchem-788	141	11	3343	3343	NUM
eurjchem-788	141	12	(nh	(nh	PROPN
eurjchem-788	141	13	)	)	PUNCT
eurjchem-788	141	14	(	(	PUNCT
eurjchem-788	141	15	nh2	nh2	PROPN
eurjchem-788	141	16	)	)	PUNCT
eurjchem-788	141	17	,	,	PUNCT
eurjchem-788	141	18	2922	2922	NUM
eurjchem-788	141	19	,	,	PUNCT
eurjchem-788	141	20	2857	2857	NUM
eurjchem-788	141	21	(ch	(ch	NOUN
eurjchem-788	141	22	)	)	PUNCT
eurjchem-788	141	23	(	(	PUNCT
eurjchem-788	141	24	ch3	ch3	PROPN
eurjchem-788	141	25	)	)	PUNCT
eurjchem-788	141	26	,	,	PUNCT
eurjchem-788	141	27	1632	1632	NUM
eurjchem-788	141	28	(nh	(nh	PROPN
eurjchem-788	141	29	)	)	PUNCT
eurjchem-788	141	30	(	(	PUNCT
eurjchem-788	141	31	nh2	nh2	PROPN
eurjchem-788	141	32	)	)	PUNCT
eurjchem-788	141	33	,	,	PUNCT
eurjchem-788	141	34	1279	1279	NUM
eurjchem-788	141	35	(	(	PUNCT
eurjchem-788	141	36	nh2	nh2	PROPN
eurjchem-788	141	37	)	)	PUNCT
eurjchem-788	141	38	.	.	PUNCT
eurjchem-788	142	1	1h	1h	NUM
eurjchem-788	142	2	nmr	nmr	NOUN
eurjchem-788	142	3	(	(	PUNCT
eurjchem-788	142	4	300	300	NUM
eurjchem-788	142	5	mhz	mhz	NOUN
eurjchem-788	142	6	,	,	PUNCT
eurjchem-788	142	7	dmso‐d6	dmso‐d6	NOUN
eurjchem-788	142	8	+	+	CCONJ
eurjchem-788	142	9	cdcl3	cdcl3	PROPN
eurjchem-788	142	10	,	,	PUNCT
eurjchem-788	142	11	δ	δ	PROPN
eurjchem-788	142	12	,	,	PUNCT
eurjchem-788	142	13	ppm	ppm	NUM
eurjchem-788	142	14	):	):	PUNCT
eurjchem-788	142	15	4.58	4.58	NUM
eurjchem-788	142	16	(	(	PUNCT
eurjchem-788	142	17	s	s	PROPN
eurjchem-788	142	18	,	,	PUNCT
eurjchem-788	142	19	br	br	PROPN
eurjchem-788	142	20	,	,	PUNCT
eurjchem-788	142	21	2h	2h	NUM
eurjchem-788	142	22	,	,	PUNCT
eurjchem-788	142	23	nh2	nh2	PROPN
eurjchem-788	142	24	)	)	PUNCT
eurjchem-788	142	25	,	,	PUNCT
eurjchem-788	142	26	2.91	2.91	NUM
eurjchem-788	142	27	(	(	PUNCT
eurjchem-788	142	28	m	m	PROPN
eurjchem-788	142	29	,	,	PUNCT
eurjchem-788	142	30	2h	2h	NUM
eurjchem-788	142	31	,	,	PUNCT
eurjchem-788	142	32	ch2	ch2	PROPN
eurjchem-788	142	33	)	)	PUNCT
eurjchem-788	142	34	,	,	PUNCT
eurjchem-788	142	35	2.53	2.53	NUM
eurjchem-788	142	36	(	(	PUNCT
eurjchem-788	142	37	s	s	PROPN
eurjchem-788	142	38	,	,	PUNCT
eurjchem-788	142	39	3h	3h	NUM
eurjchem-788	142	40	,	,	PUNCT
eurjchem-788	142	41	ch3	ch3	PROPN
eurjchem-788	142	42	)	)	PUNCT
eurjchem-788	142	43	,	,	PUNCT
eurjchem-788	142	44	2.41	2.41	NUM
eurjchem-788	142	45	(	(	PUNCT
eurjchem-788	142	46	s	s	PROPN
eurjchem-788	142	47	,	,	PUNCT
eurjchem-788	142	48	3h	3h	NUM
eurjchem-788	142	49	,	,	PUNCT
eurjchem-788	142	50	ch3	ch3	PROPN
eurjchem-788	142	51	)	)	PUNCT
eurjchem-788	142	52	,	,	PUNCT
eurjchem-788	142	53	1.96‐1.91	1.96‐1.91	NUM
eurjchem-788	142	54	(	(	PUNCT
eurjchem-788	142	55	m	m	PROPN
eurjchem-788	142	56	,	,	PUNCT
eurjchem-788	142	57	6h	6h	NUM
eurjchem-788	142	58	,	,	PUNCT
eurjchem-788	142	59	3*ch2	3*ch2	NUM
eurjchem-788	142	60	)	)	PUNCT
eurjchem-788	142	61	.	.	PUNCT
eurjchem-788	143	1	13c	13c	NOUN
eurjchem-788	143	2	nmr	nmr	NOUN
eurjchem-788	143	3	(	(	PUNCT
eurjchem-788	143	4	75	75	NUM
eurjchem-788	143	5	mhz	mhz	NOUN
eurjchem-788	143	6	,	,	PUNCT
eurjchem-788	143	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	143	8	,	,	PUNCT
eurjchem-788	143	9	δ	δ	PROPN
eurjchem-788	143	10	,	,	PUNCT
eurjchem-788	143	11	ppm	ppm	NUM
eurjchem-788	143	12	):	):	PUNCT
eurjchem-788	143	13	158.3	158.3	NUM
eurjchem-788	143	14	(	(	PUNCT
eurjchem-788	143	15	1c	1c	NOUN
eurjchem-788	143	16	,	,	PUNCT
eurjchem-788	143	17	‐s‐c	‐s‐c	ADJ
eurjchem-788	143	18	=	=	SYM
eurjchem-788	143	19	c(n)‐	c(n)‐	NOUN
eurjchem-788	143	20	)	)	PUNCT
eurjchem-788	143	21	,	,	PUNCT
eurjchem-788	143	22	153.8	153.8	NUM
eurjchem-788	143	23	(	(	PUNCT
eurjchem-788	143	24	1c	1c	NOUN
eurjchem-788	143	25	,	,	PUNCT
eurjchem-788	143	26	‐n	‐n	ADJ
eurjchem-788	143	27	=	=	NOUN
eurjchem-788	143	28	c‐ch2‐	c‐ch2‐	PROPN
eurjchem-788	143	29	)	)	PUNCT
eurjchem-788	143	30	,	,	PUNCT
eurjchem-788	143	31	147.2	147.2	NUM
eurjchem-788	143	32	(	(	PUNCT
eurjchem-788	143	33	1c	1c	NOUN
eurjchem-788	143	34	,	,	PUNCT
eurjchem-788	143	35	=	=	NOUN
eurjchem-788	143	36	c‐	c‐	NOUN
eurjchem-788	143	37	nh2	nh2	PROPN
eurjchem-788	143	38	)	)	PUNCT
eurjchem-788	143	39	,	,	PUNCT
eurjchem-788	143	40	133.1	133.1	NUM
eurjchem-788	143	41	(	(	PUNCT
eurjchem-788	143	42	1c	1c	NOUN
eurjchem-788	143	43	,	,	PUNCT
eurjchem-788	143	44	‐c	‐c	NOUN
eurjchem-788	143	45	=	=	NOUN
eurjchem-788	143	46	c‐s	c‐s	NOUN
eurjchem-788	143	47	)	)	PUNCT
eurjchem-788	143	48	,	,	PUNCT
eurjchem-788	143	49	123.6	123.6	NUM
eurjchem-788	143	50	(	(	PUNCT
eurjchem-788	143	51	1c	1c	NOUN
eurjchem-788	143	52	,	,	PUNCT
eurjchem-788	143	53	‐c	‐c	NOUN
eurjchem-788	143	54	=	=	NOUN
eurjchem-788	143	55	c‐s	c‐s	NOUN
eurjchem-788	143	56	)	)	PUNCT
eurjchem-788	143	57	,	,	PUNCT
eurjchem-788	143	58	126.3	126.3	NUM
eurjchem-788	143	59	(	(	PUNCT
eurjchem-788	143	60	1c	1c	NOUN
eurjchem-788	143	61	,	,	PUNCT
eurjchem-788	143	62	thienyl‐	thienyl‐	NOUN
eurjchem-788	143	63	c	c	NOUN
eurjchem-788	143	64	=	=	NOUN
eurjchem-788	143	65	c‐c‐nh2	c‐c‐nh2	PROPN
eurjchem-788	143	66	)	)	PUNCT
eurjchem-788	143	67	,	,	PUNCT
eurjchem-788	143	68	113.5	113.5	NUM
eurjchem-788	143	69	(	(	PUNCT
eurjchem-788	143	70	1c	1c	NOUN
eurjchem-788	143	71	,	,	PUNCT
eurjchem-788	143	72	pyridinyl‐c‐ch2	pyridinyl‐c‐ch2	NOUN
eurjchem-788	143	73	)	)	PUNCT
eurjchem-788	143	74	,	,	PUNCT
eurjchem-788	143	75	34.3	34.3	NUM
eurjchem-788	143	76	(	(	PUNCT
eurjchem-788	143	77	1c	1c	NOUN
eurjchem-788	143	78	,	,	PUNCT
eurjchem-788	143	79	‐ch2‐ch2‐	‐ch2‐ch2‐	X
eurjchem-788	143	80	ch2‐ch2‐	ch2‐ch2‐	NOUN
eurjchem-788	143	81	)	)	PUNCT
eurjchem-788	143	82	,	,	PUNCT
eurjchem-788	143	83	33.1	33.1	NUM
eurjchem-788	143	84	(	(	PUNCT
eurjchem-788	143	85	1c	1c	NOUN
eurjchem-788	143	86	,	,	PUNCT
eurjchem-788	143	87	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	143	88	)	)	PUNCT
eurjchem-788	143	89	,	,	PUNCT
eurjchem-788	143	90	27.3	27.3	NUM
eurjchem-788	143	91	(	(	PUNCT
eurjchem-788	143	92	1c	1c	NOUN
eurjchem-788	143	93	,	,	PUNCT
eurjchem-788	143	94	‐ch2‐ch2‐	‐ch2‐ch2‐	X
eurjchem-788	143	95	ch2‐ch2‐	ch2‐ch2‐	NOUN
eurjchem-788	143	96	)	)	PUNCT
eurjchem-788	143	97	,	,	PUNCT
eurjchem-788	143	98	23.5	23.5	NUM
eurjchem-788	143	99	(	(	PUNCT
eurjchem-788	143	100	1c	1c	NOUN
eurjchem-788	143	101	,	,	PUNCT
eurjchem-788	143	102	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	143	103	)	)	PUNCT
eurjchem-788	143	104	,	,	PUNCT
eurjchem-788	143	105	14.8	14.8	NUM
eurjchem-788	143	106	(	(	PUNCT
eurjchem-788	143	107	1c	1c	NOUN
eurjchem-788	143	108	,	,	PUNCT
eurjchem-788	143	109	‐ch3	‐ch3	ADJ
eurjchem-788	143	110	)	)	PUNCT
eurjchem-788	143	111	,	,	PUNCT
eurjchem-788	143	112	14.1	14.1	NUM
eurjchem-788	143	113	(	(	PUNCT
eurjchem-788	143	114	1c	1c	NOUN
eurjchem-788	143	115	,	,	PUNCT
eurjchem-788	143	116	‐ch3	‐ch3	ADJ
eurjchem-788	143	117	)	)	PUNCT
eurjchem-788	143	118	.	.	PUNCT
eurjchem-788	144	1	anal	anal	PROPN
eurjchem-788	144	2	.	.	PUNCT
eurjchem-788	144	3	calcd	calcd	NOUN
eurjchem-788	144	4	.	.	PUNCT
eurjchem-788	145	1	for	for	ADP
eurjchem-788	145	2	c13h16n2s	c13h16n2s	PROPN
eurjchem-788	145	3	:	:	PUNCT
eurjchem-788	145	4	c	c	X
eurjchem-788	145	5	,	,	PUNCT
eurjchem-788	145	6	67.20	67.20	NUM
eurjchem-788	145	7	;	;	PUNCT
eurjchem-788	145	8	h	h	NOUN
eurjchem-788	145	9	,	,	PUNCT
eurjchem-788	145	10	6.93	6.93	NUM
eurjchem-788	145	11	;	;	PUNCT
eurjchem-788	145	12	n	n	CCONJ
eurjchem-788	145	13	,	,	PUNCT
eurjchem-788	145	14	12.07	12.07	NUM
eurjchem-788	145	15	.	.	PUNCT
eurjchem-788	145	16	found	find	VERB
eurjchem-788	145	17	:	:	PUNCT
eurjchem-788	146	1	c	c	X
eurjchem-788	146	2	,	,	PUNCT
eurjchem-788	146	3	67.13	67.13	NUM
eurjchem-788	146	4	;	;	PUNCT
eurjchem-788	146	5	h	h	NOUN
eurjchem-788	146	6	,	,	PUNCT
eurjchem-788	146	7	7.04	7.04	NUM
eurjchem-788	146	8	;	;	PUNCT
eurjchem-788	146	9	n	n	CCONJ
eurjchem-788	146	10	,	,	PUNCT
eurjchem-788	146	11	12.26	12.26	NUM
eurjchem-788	146	12	%	%	NOUN
eurjchem-788	146	13	.	.	PUNCT
eurjchem-788	147	1	4‐amino‐3‐(4‐chlorophenyl)‐5,6,7,8‐tetrahydrothieno[2,3‐	4‐amino‐3‐(4‐chlorophenyl)‐5,6,7,8‐tetrahydrothieno[2,3‐	NUM
eurjchem-788	147	2	b]quinoline	b]quinoline	PROPN
eurjchem-788	147	3	(	(	PUNCT
eurjchem-788	147	4	3c	3c	NUM
eurjchem-788	147	5	):	):	PUNCT
eurjchem-788	147	6	following	follow	VERB
eurjchem-788	147	7	the	the	DET
eurjchem-788	147	8	general	general	ADJ
eurjchem-788	147	9	method	method	NOUN
eurjchem-788	147	10	for	for	ADP
eurjchem-788	147	11	the	the	DET
eurjchem-788	147	12	friedländer	friedländer	NOUN
eurjchem-788	147	13	reaction	reaction	NOUN
eurjchem-788	147	14	,	,	PUNCT
eurjchem-788	147	15	alcl3	alcl3	PROPN
eurjchem-788	147	16	(	(	PUNCT
eurjchem-788	147	17	800	800	NUM
eurjchem-788	147	18	mg	mg	NUM
eurjchem-788	147	19	)	)	PUNCT
eurjchem-788	147	20	or	or	CCONJ
eurjchem-788	147	21	activated	activate	VERB
eurjchem-788	147	22	bentonite	bentonite	NOUN
eurjchem-788	147	23	(	(	PUNCT
eurjchem-788	147	24	1000	1000	NUM
eurjchem-788	147	25	mg	mg	NOUN
eurjchem-788	147	26	)	)	PUNCT
eurjchem-788	147	27	in	in	ADP
eurjchem-788	147	28	dry	dry	ADJ
eurjchem-788	147	29	1,2‐dichloroethane	1,2‐dichloroethane	NOUN
eurjchem-788	147	30	(	(	PUNCT
eurjchem-788	147	31	50	50	NUM
eurjchem-788	147	32	ml	ml	NOUN
eurjchem-788	147	33	)	)	PUNCT
eurjchem-788	147	34	was	be	AUX
eurjchem-788	147	35	reacted	react	VERB
eurjchem-788	147	36	with	with	ADP
eurjchem-788	147	37	cyclohexanone	cyclohexanone	PROPN
eurjchem-788	147	38	(	(	PUNCT
eurjchem-788	147	39	10	10	NUM
eurjchem-788	147	40	mmol	mmol	NOUN
eurjchem-788	147	41	)	)	PUNCT
eurjchem-788	147	42	and	and	CCONJ
eurjchem-788	147	43	aminothiophene	aminothiophene	NOUN
eurjchem-788	147	44	1c	1c	NOUN
eurjchem-788	147	45	(	(	PUNCT
eurjchem-788	147	46	5	5	NUM
eurjchem-788	147	47	mmol	mmol	NOUN
eurjchem-788	147	48	)	)	PUNCT
eurjchem-788	147	49	.	.	PUNCT
eurjchem-788	148	1	dridi	dridi	PROPN
eurjchem-788	148	2	et	et	PROPN
eurjchem-788	148	3	al	al	PROPN
eurjchem-788	148	4	.	.	PUNCT
eurjchem-788	148	5	/	/	SYM
eurjchem-788	148	6	european	european	PROPN
eurjchem-788	148	7	journal	journal	PROPN
eurjchem-788	148	8	of	of	ADP
eurjchem-788	148	9	chemistry	chemistry	NOUN
eurjchem-788	148	10	4	4	NUM
eurjchem-788	148	11	(	(	PUNCT
eurjchem-788	148	12	3	3	NUM
eurjchem-788	148	13	)	)	PUNCT
eurjchem-788	148	14	(	(	PUNCT
eurjchem-788	148	15	2013	2013	NUM
eurjchem-788	148	16	)	)	PUNCT
eurjchem-788	148	17	216‐219	216‐219	ADJ
eurjchem-788	148	18	219	219	NUM
eurjchem-788	148	19	table	table	NOUN
eurjchem-788	148	20	1	1	NUM
eurjchem-788	148	21	.	.	PUNCT
eurjchem-788	148	22	percentage	percentage	NOUN
eurjchem-788	148	23	conversion	conversion	NOUN
eurjchem-788	148	24	of	of	ADP
eurjchem-788	148	25	compound	compound	NOUN
eurjchem-788	148	26	2	2	NUM
eurjchem-788	148	27	and	and	CCONJ
eurjchem-788	148	28	3	3	NUM
eurjchem-788	148	29	in	in	ADP
eurjchem-788	148	30	the	the	DET
eurjchem-788	148	31	presence	presence	NOUN
eurjchem-788	148	32	of	of	ADP
eurjchem-788	148	33	catalytic	catalytic	ADJ
eurjchem-788	148	34	amount	amount	NOUN
eurjchem-788	148	35	of	of	ADP
eurjchem-788	148	36	alcl3	alcl3	NOUN
eurjchem-788	148	37	and	and	CCONJ
eurjchem-788	148	38	acid	acid	ADJ
eurjchem-788	148	39	activated	activate	VERB
eurjchem-788	148	40	bentonite	bentonite	NOUN
eurjchem-788	148	41	.	.	PUNCT
eurjchem-788	149	1	compound	compound	NOUN
eurjchem-788	149	2	2a	2a	NUM
eurjchem-788	149	3	2b	2b	NUM
eurjchem-788	149	4	2c	2c	NUM
eurjchem-788	149	5	2d	2d	NOUN
eurjchem-788	149	6	2e	2e	PROPN
eurjchem-788	149	7	3a	3a	NUM
eurjchem-788	149	8	3b	3b	NUM
eurjchem-788	149	9	3c	3c	NUM
eurjchem-788	149	10	yield	yield	NOUN
eurjchem-788	149	11	(	(	PUNCT
eurjchem-788	149	12	%	%	INTJ
eurjchem-788	149	13	)	)	PUNCT
eurjchem-788	150	1	alcl3	alcl3	PROPN
eurjchem-788	150	2	used	use	VERB
eurjchem-788	150	3	as	as	ADP
eurjchem-788	150	4	a	a	DET
eurjchem-788	150	5	support	support	NOUN
eurjchem-788	150	6	catalyst	catalyst	NOUN
eurjchem-788	150	7	52	52	NUM
eurjchem-788	150	8	58	58	NUM
eurjchem-788	150	9	55	55	NUM
eurjchem-788	150	10	62	62	NUM
eurjchem-788	150	11	53	53	NUM
eurjchem-788	150	12	78	78	NUM
eurjchem-788	150	13	83	83	NUM
eurjchem-788	150	14	77	77	NUM
eurjchem-788	150	15	activated	activated	ADJ
eurjchem-788	150	16	bentonite	bentonite	NOUN
eurjchem-788	150	17	used	use	VERB
eurjchem-788	150	18	as	as	ADP
eurjchem-788	150	19	a	a	DET
eurjchem-788	150	20	support	support	NOUN
eurjchem-788	150	21	catalyst	catalyst	NOUN
eurjchem-788	150	22	67	67	NUM
eurjchem-788	150	23	71	71	NUM
eurjchem-788	150	24	64	64	NUM
eurjchem-788	150	25	73	73	NUM
eurjchem-788	150	26	68	68	NUM
eurjchem-788	150	27	93	93	NUM
eurjchem-788	150	28	88	88	NUM
eurjchem-788	150	29	86	86	NUM
eurjchem-788	150	30	scheme	scheme	NOUN
eurjchem-788	150	31	3	3	NUM
eurjchem-788	150	32	the	the	DET
eurjchem-788	150	33	mixture	mixture	NOUN
eurjchem-788	150	34	was	be	AUX
eurjchem-788	150	35	refluxed	refluxe	VERB
eurjchem-788	150	36	for	for	ADP
eurjchem-788	150	37	24	24	NUM
eurjchem-788	150	38	h.	h.	PROPN
eurjchem-788	151	1	work‐up	work‐up	PROPN
eurjchem-788	151	2	and	and	CCONJ
eurjchem-788	151	3	chromatography	chromatography	NOUN
eurjchem-788	151	4	provided	provide	VERB
eurjchem-788	151	5	compound	compound	NOUN
eurjchem-788	151	6	3c	3c	NUM
eurjchem-788	151	7	.	.	PUNCT
eurjchem-788	152	1	color	color	NOUN
eurjchem-788	152	2	:	:	PUNCT
eurjchem-788	152	3	orange	orange	ADJ
eurjchem-788	152	4	.	.	PUNCT
eurjchem-788	153	1	yield	yield	NOUN
eurjchem-788	153	2	:	:	PUNCT
eurjchem-788	153	3	86	86	NUM
eurjchem-788	153	4	%	%	NOUN
eurjchem-788	153	5	.	.	PUNCT
eurjchem-788	154	1	m.p	m.p	PROPN
eurjchem-788	154	2	.	.	PROPN
eurjchem-788	154	3	:	:	PUNCT
eurjchem-788	155	1	177‐179	177‐179	NUM
eurjchem-788	155	2	°	°	SYM
eurjchem-788	155	3	c	c	X
eurjchem-788	155	4	.	.	PUNCT
eurjchem-788	156	1	ft‐ir	ft‐ir	NOUN
eurjchem-788	156	2	(	(	PUNCT
eurjchem-788	156	3	kbr	kbr	PROPN
eurjchem-788	156	4	,	,	PUNCT
eurjchem-788	156	5	ν	ν	PROPN
eurjchem-788	156	6	,	,	PUNCT
eurjchem-788	156	7	cm‐1	cm‐1	PROPN
eurjchem-788	156	8	):	):	PUNCT
eurjchem-788	156	9	3481	3481	NUM
eurjchem-788	156	10	,	,	PUNCT
eurjchem-788	156	11	3346	3346	NUM
eurjchem-788	156	12	(nh	(nh	PROPN
eurjchem-788	156	13	)	)	PUNCT
eurjchem-788	156	14	(	(	PUNCT
eurjchem-788	156	15	nh2	nh2	PROPN
eurjchem-788	156	16	)	)	PUNCT
eurjchem-788	156	17	,	,	PUNCT
eurjchem-788	156	18	1621	1621	NUM
eurjchem-788	156	19	(nh	(nh	PROPN
eurjchem-788	156	20	)	)	PUNCT
eurjchem-788	156	21	(	(	PUNCT
eurjchem-788	156	22	nh2	nh2	PROPN
eurjchem-788	156	23	)	)	PUNCT
eurjchem-788	156	24	,	,	PUNCT
eurjchem-788	156	25	1447	1447	NUM
eurjchem-788	156	26	(	(	PUNCT
eurjchem-788	156	27	ch2	ch2	PROPN
eurjchem-788	156	28	)	)	PUNCT
eurjchem-788	156	29	,	,	PUNCT
eurjchem-788	156	30	831	831	NUM
eurjchem-788	156	31	(	(	PUNCT
eurjchem-788	156	32	c‐cl	c‐cl	PROPN
eurjchem-788	156	33	)	)	PUNCT
eurjchem-788	156	34	.	.	PUNCT
eurjchem-788	157	1	1h	1h	NUM
eurjchem-788	157	2	nmr	nmr	NOUN
eurjchem-788	157	3	(	(	PUNCT
eurjchem-788	157	4	300	300	NUM
eurjchem-788	157	5	mhz	mhz	NOUN
eurjchem-788	157	6	,	,	PUNCT
eurjchem-788	157	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	157	8	,	,	PUNCT
eurjchem-788	157	9	δ	δ	PROPN
eurjchem-788	157	10	,	,	PUNCT
eurjchem-788	157	11	ppm	ppm	NUM
eurjchem-788	157	12	):	):	PUNCT
eurjchem-788	157	13	7.37	7.37	NUM
eurjchem-788	157	14	(	(	PUNCT
eurjchem-788	157	15	m	m	PROPN
eurjchem-788	157	16	,	,	PUNCT
eurjchem-788	157	17	4h	4h	NUM
eurjchem-788	157	18	,	,	PUNCT
eurjchem-788	157	19	ar‐h	ar‐h	PROPN
eurjchem-788	157	20	)	)	PUNCT
eurjchem-788	157	21	,	,	PUNCT
eurjchem-788	157	22	7.01	7.01	NUM
eurjchem-788	157	23	(	(	PUNCT
eurjchem-788	157	24	s	s	PROPN
eurjchem-788	157	25	,	,	PUNCT
eurjchem-788	157	26	1h	1h	NUM
eurjchem-788	157	27	,	,	PUNCT
eurjchem-788	157	28	thienyl‐	thienyl‐	NOUN
eurjchem-788	157	29	h	h	NOUN
eurjchem-788	157	30	)	)	PUNCT
eurjchem-788	157	31	,	,	PUNCT
eurjchem-788	157	32	4.54	4.54	NUM
eurjchem-788	157	33	(	(	PUNCT
eurjchem-788	157	34	s	s	PROPN
eurjchem-788	157	35	,	,	PUNCT
eurjchem-788	157	36	br	br	PROPN
eurjchem-788	157	37	,	,	PUNCT
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eurjchem-788	157	39	,	,	PUNCT
eurjchem-788	157	40	nh2	nh2	PROPN
eurjchem-788	157	41	)	)	PUNCT
eurjchem-788	157	42	,	,	PUNCT
eurjchem-788	157	43	2.97	2.97	NUM
eurjchem-788	157	44	(	(	PUNCT
eurjchem-788	157	45	m	m	PROPN
eurjchem-788	157	46	,	,	PUNCT
eurjchem-788	157	47	2h	2h	NUM
eurjchem-788	157	48	,	,	PUNCT
eurjchem-788	157	49	‐n	‐n	NOUN
eurjchem-788	157	50	=	=	NOUN
eurjchem-788	157	51	c‐ch2	c‐ch2	PROPN
eurjchem-788	157	52	)	)	PUNCT
eurjchem-788	157	53	,	,	PUNCT
eurjchem-788	157	54	2.51	2.51	NUM
eurjchem-788	157	55	(	(	PUNCT
eurjchem-788	157	56	m	m	PROPN
eurjchem-788	157	57	,	,	PUNCT
eurjchem-788	157	58	2h	2h	NUM
eurjchem-788	157	59	,	,	PUNCT
eurjchem-788	157	60	=	=	NOUN
eurjchem-788	157	61	c‐ch2	c‐ch2	PROPN
eurjchem-788	157	62	)	)	PUNCT
eurjchem-788	157	63	,	,	PUNCT
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eurjchem-788	157	67	,	,	PUNCT
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eurjchem-788	157	69	,	,	PUNCT
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eurjchem-788	157	71	)	)	PUNCT
eurjchem-788	157	72	.	.	PUNCT
eurjchem-788	158	1	13c	13c	NOUN
eurjchem-788	158	2	nmr	nmr	NOUN
eurjchem-788	158	3	(	(	PUNCT
eurjchem-788	158	4	75	75	NUM
eurjchem-788	158	5	mhz	mhz	NOUN
eurjchem-788	158	6	,	,	PUNCT
eurjchem-788	158	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-788	158	8	,	,	PUNCT
eurjchem-788	158	9	δ	δ	PROPN
eurjchem-788	158	10	,	,	PUNCT
eurjchem-788	158	11	ppm	ppm	NUM
eurjchem-788	158	12	):	):	PUNCT
eurjchem-788	158	13	159.1	159.1	NUM
eurjchem-788	158	14	(	(	PUNCT
eurjchem-788	158	15	1c	1c	NOUN
eurjchem-788	158	16	,	,	PUNCT
eurjchem-788	158	17	‐s‐c	‐s‐c	ADJ
eurjchem-788	158	18	=	=	SYM
eurjchem-788	158	19	c(n)‐	c(n)‐	NOUN
eurjchem-788	158	20	)	)	PUNCT
eurjchem-788	158	21	,	,	PUNCT
eurjchem-788	158	22	155.9	155.9	NUM
eurjchem-788	158	23	(	(	PUNCT
eurjchem-788	158	24	1c	1c	NOUN
eurjchem-788	158	25	,	,	PUNCT
eurjchem-788	158	26	‐n	‐n	ADJ
eurjchem-788	158	27	=	=	NOUN
eurjchem-788	158	28	c‐ch2‐	c‐ch2‐	PROPN
eurjchem-788	158	29	)	)	PUNCT
eurjchem-788	158	30	,	,	PUNCT
eurjchem-788	158	31	147.2	147.2	NUM
eurjchem-788	158	32	(	(	PUNCT
eurjchem-788	158	33	1c	1c	NOUN
eurjchem-788	158	34	,	,	PUNCT
eurjchem-788	158	35	=	=	NOUN
eurjchem-788	158	36	c‐nh2	c‐nh2	PROPN
eurjchem-788	158	37	)	)	PUNCT
eurjchem-788	158	38	,	,	PUNCT
eurjchem-788	158	39	135.8	135.8	NUM
eurjchem-788	158	40	(	(	PUNCT
eurjchem-788	158	41	1c	1c	NOUN
eurjchem-788	158	42	,	,	PUNCT
eurjchem-788	158	43	‐c	‐c	NOUN
eurjchem-788	158	44	=	=	NOUN
eurjchem-788	158	45	c‐s	c‐s	NOUN
eurjchem-788	158	46	)	)	PUNCT
eurjchem-788	158	47	,	,	PUNCT
eurjchem-788	158	48	134.3	134.3	NUM
eurjchem-788	158	49	(	(	PUNCT
eurjchem-788	158	50	1c	1c	NOUN
eurjchem-788	158	51	,	,	PUNCT
eurjchem-788	158	52	c‐ar	c‐ar	NUM
eurjchem-788	158	53	)	)	PUNCT
eurjchem-788	158	54	,	,	PUNCT
eurjchem-788	158	55	133.7	133.7	NUM
eurjchem-788	158	56	(	(	PUNCT
eurjchem-788	158	57	1c	1c	NOUN
eurjchem-788	158	58	,	,	PUNCT
eurjchem-788	158	59	cl‐c‐	cl‐c‐	PROPN
eurjchem-788	158	60	ar	ar	PROPN
eurjchem-788	158	61	)	)	PUNCT
eurjchem-788	158	62	,	,	PUNCT
eurjchem-788	158	63	131.2	131.2	NUM
eurjchem-788	158	64	(	(	PUNCT
eurjchem-788	158	65	2c	2c	NOUN
eurjchem-788	158	66	,	,	PUNCT
eurjchem-788	158	67	ch‐ar	ch‐ar	NUM
eurjchem-788	158	68	)	)	PUNCT
eurjchem-788	158	69	,	,	PUNCT
eurjchem-788	158	70	129.1	129.1	NUM
eurjchem-788	158	71	(	(	PUNCT
eurjchem-788	158	72	2c	2c	NOUN
eurjchem-788	158	73	,	,	PUNCT
eurjchem-788	158	74	ch‐ar	ch‐ar	NUM
eurjchem-788	158	75	)	)	PUNCT
eurjchem-788	158	76	,	,	PUNCT
eurjchem-788	158	77	120.2	120.2	NUM
eurjchem-788	158	78	(	(	PUNCT
eurjchem-788	158	79	1c	1c	NOUN
eurjchem-788	158	80	,	,	PUNCT
eurjchem-788	158	81	‐c	‐c	NOUN
eurjchem-788	158	82	=	=	NOUN
eurjchem-788	158	83	c‐s	c‐s	NOUN
eurjchem-788	158	84	)	)	PUNCT
eurjchem-788	158	85	,	,	PUNCT
eurjchem-788	158	86	115.9	115.9	NUM
eurjchem-788	158	87	(	(	PUNCT
eurjchem-788	158	88	1c	1c	NOUN
eurjchem-788	158	89	,	,	PUNCT
eurjchem-788	158	90	thienyl‐c	thienyl‐c	PROPN
eurjchem-788	158	91	=	=	NOUN
eurjchem-788	158	92	c‐c‐nh2	c‐c‐nh2	PROPN
eurjchem-788	158	93	)	)	PUNCT
eurjchem-788	158	94	,	,	PUNCT
eurjchem-788	158	95	113.8	113.8	NUM
eurjchem-788	158	96	(	(	PUNCT
eurjchem-788	158	97	1c	1c	NOUN
eurjchem-788	158	98	,	,	PUNCT
eurjchem-788	158	99	pyridinyl‐c‐ch2	pyridinyl‐c‐ch2	NOUN
eurjchem-788	158	100	)	)	PUNCT
eurjchem-788	158	101	,	,	PUNCT
eurjchem-788	158	102	33.7	33.7	NUM
eurjchem-788	158	103	(	(	PUNCT
eurjchem-788	158	104	1c	1c	NOUN
eurjchem-788	158	105	,	,	PUNCT
eurjchem-788	158	106	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	158	107	)	)	PUNCT
eurjchem-788	158	108	,	,	PUNCT
eurjchem-788	158	109	23.2	23.2	NUM
eurjchem-788	158	110	(	(	PUNCT
eurjchem-788	158	111	1c	1c	NOUN
eurjchem-788	158	112	,	,	PUNCT
eurjchem-788	158	113	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	158	114	)	)	PUNCT
eurjchem-788	158	115	,	,	PUNCT
eurjchem-788	158	116	22.7	22.7	NUM
eurjchem-788	158	117	(	(	PUNCT
eurjchem-788	158	118	1c	1c	NOUN
eurjchem-788	158	119	,	,	PUNCT
eurjchem-788	158	120	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	158	121	)	)	PUNCT
eurjchem-788	158	122	,	,	PUNCT
eurjchem-788	158	123	22.4	22.4	NUM
eurjchem-788	158	124	(	(	PUNCT
eurjchem-788	158	125	1c	1c	NOUN
eurjchem-788	158	126	,	,	PUNCT
eurjchem-788	158	127	‐ch2‐ch2‐ch2‐ch2‐	‐ch2‐ch2‐ch2‐ch2‐	NUM
eurjchem-788	158	128	)	)	PUNCT
eurjchem-788	158	129	.	.	PUNCT
eurjchem-788	159	1	anal	anal	PROPN
eurjchem-788	159	2	.	.	PUNCT
eurjchem-788	159	3	calcd	calcd	NOUN
eurjchem-788	159	4	.	.	PUNCT
eurjchem-788	160	1	for	for	ADP
eurjchem-788	160	2	c17h15cln2s	c17h15cln2s	ADJ
eurjchem-788	160	3	:	:	PUNCT
eurjchem-788	160	4	c	c	X
eurjchem-788	160	5	,	,	PUNCT
eurjchem-788	160	6	64.84	64.84	NUM
eurjchem-788	160	7	;	;	PUNCT
eurjchem-788	160	8	h	h	NOUN
eurjchem-788	160	9	,	,	PUNCT
eurjchem-788	160	10	4.80	4.80	NUM
eurjchem-788	160	11	;	;	PUNCT
eurjchem-788	160	12	n	n	CCONJ
eurjchem-788	160	13	,	,	PUNCT
eurjchem-788	160	14	8.90	8.90	NUM
eurjchem-788	160	15	.	.	PUNCT
eurjchem-788	160	16	found	find	VERB
eurjchem-788	160	17	:	:	PUNCT
eurjchem-788	161	1	c	c	X
eurjchem-788	161	2	,	,	PUNCT
eurjchem-788	161	3	64.79	64.79	NUM
eurjchem-788	161	4	;	;	PUNCT
eurjchem-788	161	5	h	h	NOUN
eurjchem-788	161	6	,	,	PUNCT
eurjchem-788	161	7	4.75	4.75	NUM
eurjchem-788	161	8	;	;	PUNCT
eurjchem-788	161	9	n	n	CCONJ
eurjchem-788	161	10	,	,	PUNCT
eurjchem-788	161	11	8.97	8.97	NUM
eurjchem-788	161	12	%	%	NOUN
eurjchem-788	161	13	.	.	PUNCT
eurjchem-788	162	1	3	3	X
eurjchem-788	162	2	.	.	NOUN
eurjchem-788	162	3	results	result	NOUN
eurjchem-788	162	4	and	and	CCONJ
eurjchem-788	162	5	discussion	discussion	NOUN
eurjchem-788	162	6	different	different	ADJ
eurjchem-788	162	7	synthetic	synthetic	ADJ
eurjchem-788	162	8	approaches	approach	NOUN
eurjchem-788	162	9	for	for	ADP
eurjchem-788	162	10	the	the	DET
eurjchem-788	162	11	preparation	preparation	NOUN
eurjchem-788	162	12	of	of	ADP
eurjchem-788	162	13	aminopyridine	aminopyridine	ADJ
eurjchem-788	162	14	rings	ring	NOUN
eurjchem-788	162	15	have	have	AUX
eurjchem-788	162	16	been	be	AUX
eurjchem-788	162	17	reported	report	VERB
eurjchem-788	162	18	,	,	PUNCT
eurjchem-788	162	19	the	the	DET
eurjchem-788	162	20	friedländer	friedländer	NOUN
eurjchem-788	162	21	reaction	reaction	NOUN
eurjchem-788	162	22	being	be	AUX
eurjchem-788	162	23	one	one	NUM
eurjchem-788	162	24	of	of	ADP
eurjchem-788	162	25	the	the	DET
eurjchem-788	162	26	simplest	simple	ADJ
eurjchem-788	162	27	and	and	CCONJ
eurjchem-788	162	28	most	most	ADV
eurjchem-788	162	29	efficient	efficient	ADJ
eurjchem-788	162	30	methods	method	NOUN
eurjchem-788	162	31	[	[	X
eurjchem-788	162	32	11	11	NUM
eurjchem-788	162	33	]	]	PUNCT
eurjchem-788	162	34	.	.	PUNCT
eurjchem-788	163	1	friedländer	friedländer	PROPN
eurjchem-788	163	2	reaction	reaction	NOUN
eurjchem-788	163	3	is	be	AUX
eurjchem-788	163	4	a	a	DET
eurjchem-788	163	5	base	base	NOUN
eurjchem-788	163	6	or	or	CCONJ
eurjchem-788	163	7	acid	acid	ADJ
eurjchem-788	163	8	catalysed	catalyse	VERB
eurjchem-788	163	9	condensation	condensation	NOUN
eurjchem-788	163	10	of	of	ADP
eurjchem-788	163	11	an	an	DET
eurjchem-788	163	12	aromatic	aromatic	ADJ
eurjchem-788	163	13	2‐amino	2‐amino	NUM
eurjchem-788	163	14	substituted	substitute	VERB
eurjchem-788	163	15	carbonyl	carbonyl	NOUN
eurjchem-788	163	16	compounds	compound	NOUN
eurjchem-788	163	17	with	with	ADP
eurjchem-788	163	18	carbonyl	carbonyl	NOUN
eurjchem-788	163	19	derivatives	derivative	NOUN
eurjchem-788	163	20	containing	contain	VERB
eurjchem-788	163	21	a	a	DET
eurjchem-788	163	22	reactive	reactive	NOUN
eurjchem-788	163	23	α‐	α‐	PROPN
eurjchem-788	163	24	methylene	methylene	NOUN
eurjchem-788	163	25	group	group	NOUN
eurjchem-788	163	26	(	(	PUNCT
eurjchem-788	163	27	scheme	scheme	NOUN
eurjchem-788	163	28	3	3	NUM
eurjchem-788	163	29	)	)	PUNCT
eurjchem-788	163	30	.	.	PUNCT
eurjchem-788	164	1	many	many	ADJ
eurjchem-788	164	2	studies	study	NOUN
eurjchem-788	164	3	have	have	AUX
eurjchem-788	164	4	been	be	AUX
eurjchem-788	164	5	undertaken	undertake	VERB
eurjchem-788	164	6	with	with	ADP
eurjchem-788	164	7	the	the	DET
eurjchem-788	164	8	aim	aim	NOUN
eurjchem-788	164	9	of	of	ADP
eurjchem-788	164	10	developing	develop	VERB
eurjchem-788	164	11	new	new	ADJ
eurjchem-788	164	12	catalysts	catalyst	NOUN
eurjchem-788	164	13	operating	operate	VERB
eurjchem-788	164	14	under	under	ADP
eurjchem-788	164	15	milder	mild	ADJ
eurjchem-788	164	16	conditions	condition	NOUN
eurjchem-788	164	17	.	.	PUNCT
eurjchem-788	165	1	the	the	DET
eurjchem-788	165	2	usual	usual	ADJ
eurjchem-788	165	3	acid	acid	NOUN
eurjchem-788	165	4	catalyst	catalyst	NOUN
eurjchem-788	165	5	promoted	promote	VERB
eurjchem-788	165	6	friedländer	friedländer	NOUN
eurjchem-788	165	7	reaction	reaction	NOUN
eurjchem-788	165	8	was	be	AUX
eurjchem-788	165	9	lewis	lewis	PROPN
eurjchem-788	165	10	acid	acid	PROPN
eurjchem-788	165	11	such	such	ADJ
eurjchem-788	165	12	as	as	ADP
eurjchem-788	165	13	al2o3	al2o3	PROPN
eurjchem-788	165	14	,	,	PUNCT
eurjchem-788	165	15	sio2	sio2	NOUN
eurjchem-788	165	16	and	and	CCONJ
eurjchem-788	165	17	alcl3	alcl3	PROPN
eurjchem-788	165	18	.	.	PROPN
eurjchem-788	165	19	clays	clay	NOUN
eurjchem-788	165	20	such	such	ADJ
eurjchem-788	165	21	as	as	ADP
eurjchem-788	165	22	acid	acid	ADJ
eurjchem-788	165	23	activated	activate	VERB
eurjchem-788	165	24	bentonites	bentonite	NOUN
eurjchem-788	165	25	have	have	AUX
eurjchem-788	165	26	been	be	AUX
eurjchem-788	165	27	used	use	VERB
eurjchem-788	165	28	as	as	ADP
eurjchem-788	165	29	solid	solid	ADJ
eurjchem-788	165	30	catalyst	catalyst	NOUN
eurjchem-788	165	31	supports	support	NOUN
eurjchem-788	165	32	for	for	ADP
eurjchem-788	165	33	a	a	DET
eurjchem-788	165	34	number	number	NOUN
eurjchem-788	165	35	of	of	ADP
eurjchem-788	165	36	organic	organic	ADJ
eurjchem-788	165	37	synthesis	synthesis	NOUN
eurjchem-788	165	38	[	[	X
eurjchem-788	165	39	12‐	12‐	NUM
eurjchem-788	165	40	15	15	NUM
eurjchem-788	165	41	]	]	PUNCT
eurjchem-788	165	42	.	.	PUNCT
eurjchem-788	166	1	the	the	DET
eurjchem-788	166	2	advantages	advantage	NOUN
eurjchem-788	166	3	of	of	ADP
eurjchem-788	166	4	using	use	VERB
eurjchem-788	166	5	these	these	DET
eurjchem-788	166	6	catalysts	catalyst	NOUN
eurjchem-788	166	7	reside	reside	VERB
eurjchem-788	166	8	in	in	ADP
eurjchem-788	166	9	the	the	DET
eurjchem-788	166	10	association	association	NOUN
eurjchem-788	166	11	of	of	ADP
eurjchem-788	166	12	lewis	lewis	PROPN
eurjchem-788	166	13	and	and	CCONJ
eurjchem-788	166	14	bronsted	bronste	VERB
eurjchem-788	166	15	site	site	NOUN
eurjchem-788	166	16	acids	acid	NOUN
eurjchem-788	166	17	,	,	PUNCT
eurjchem-788	166	18	the	the	DET
eurjchem-788	166	19	good	good	ADJ
eurjchem-788	166	20	absorptive	absorptive	ADJ
eurjchem-788	166	21	capacity	capacity	NOUN
eurjchem-788	166	22	and	and	CCONJ
eurjchem-788	166	23	the	the	DET
eurjchem-788	166	24	simple	simple	ADJ
eurjchem-788	166	25	work‐up	work‐up	ADJ
eurjchem-788	166	26	procedure	procedure	NOUN
eurjchem-788	166	27	as	as	SCONJ
eurjchem-788	166	28	the	the	DET
eurjchem-788	166	29	separation	separation	NOUN
eurjchem-788	166	30	of	of	ADP
eurjchem-788	166	31	the	the	DET
eurjchem-788	166	32	spent	spend	VERB
eurjchem-788	166	33	catalyst	catalyst	NOUN
eurjchem-788	166	34	is	be	AUX
eurjchem-788	166	35	achieved	achieve	VERB
eurjchem-788	166	36	by	by	ADP
eurjchem-788	166	37	filtration	filtration	NOUN
eurjchem-788	166	38	.	.	PUNCT
eurjchem-788	167	1	otherwise	otherwise	ADV
eurjchem-788	167	2	,	,	PUNCT
eurjchem-788	167	3	they	they	PRON
eurjchem-788	167	4	have	have	VERB
eurjchem-788	167	5	considerable	considerable	ADJ
eurjchem-788	167	6	potential	potential	NOUN
eurjchem-788	167	7	as	as	ADP
eurjchem-788	167	8	environmental	environmental	ADJ
eurjchem-788	167	9	friendly	friendly	ADJ
eurjchem-788	167	10	solid	solid	ADJ
eurjchem-788	167	11	acid	acid	NOUN
eurjchem-788	167	12	catalysts	catalyst	NOUN
eurjchem-788	167	13	and	and	CCONJ
eurjchem-788	167	14	they	they	PRON
eurjchem-788	167	15	can	can	AUX
eurjchem-788	167	16	be	be	AUX
eurjchem-788	167	17	regenerated	regenerate	VERB
eurjchem-788	167	18	and	and	CCONJ
eurjchem-788	167	19	reused	reuse	VERB
eurjchem-788	167	20	.	.	PUNCT
eurjchem-788	168	1	in	in	ADP
eurjchem-788	168	2	this	this	DET
eurjchem-788	168	3	present	present	ADJ
eurjchem-788	168	4	paper	paper	NOUN
eurjchem-788	168	5	,	,	PUNCT
eurjchem-788	168	6	we	we	PRON
eurjchem-788	168	7	report	report	VERB
eurjchem-788	168	8	our	our	PRON
eurjchem-788	168	9	recent	recent	ADJ
eurjchem-788	168	10	studies	study	NOUN
eurjchem-788	168	11	on	on	ADP
eurjchem-788	168	12	the	the	DET
eurjchem-788	168	13	synthesis	synthesis	NOUN
eurjchem-788	168	14	of	of	ADP
eurjchem-788	168	15	4‐aminothienoquinolinones	4‐aminothienoquinolinone	NOUN
eurjchem-788	168	16	2	2	NUM
eurjchem-788	168	17	and	and	CCONJ
eurjchem-788	168	18	their	their	PRON
eurjchem-788	168	19	tacrine	tacrine	ADJ
eurjchem-788	168	20	analogues	analogue	NOUN
eurjchem-788	168	21	derivatives	derivative	NOUN
eurjchem-788	168	22	3	3	NUM
eurjchem-788	169	1	and	and	CCONJ
eurjchem-788	169	2	we	we	PRON
eurjchem-788	169	3	are	be	AUX
eurjchem-788	169	4	interested	interested	ADJ
eurjchem-788	169	5	in	in	ADP
eurjchem-788	169	6	the	the	DET
eurjchem-788	169	7	development	development	NOUN
eurjchem-788	169	8	of	of	ADP
eurjchem-788	169	9	environmentally	environmentally	ADV
eurjchem-788	169	10	friendly	friendly	ADJ
eurjchem-788	169	11	catalyst	catalyst	NOUN
eurjchem-788	169	12	such	such	ADJ
eurjchem-788	169	13	as	as	ADP
eurjchem-788	169	14	activated	activated	ADJ
eurjchem-788	169	15	bentonite	bentonite	NOUN
eurjchem-788	169	16	in	in	ADP
eurjchem-788	169	17	the	the	DET
eurjchem-788	169	18	friedländer	friedländer	NOUN
eurjchem-788	169	19	reaction	reaction	NOUN
eurjchem-788	169	20	.	.	PUNCT
eurjchem-788	170	1	the	the	DET
eurjchem-788	170	2	results	result	NOUN
eurjchem-788	170	3	of	of	ADP
eurjchem-788	170	4	the	the	DET
eurjchem-788	170	5	friedländer	friedländer	NOUN
eurjchem-788	170	6	reaction	reaction	NOUN
eurjchem-788	170	7	of	of	ADP
eurjchem-788	170	8	substituted	substitute	VERB
eurjchem-788	170	9	2‐aminothiophene‐3‐	2‐aminothiophene‐3‐	NUM
eurjchem-788	170	10	carbonitrile	carbonitrile	NOUN
eurjchem-788	170	11	with	with	ADP
eurjchem-788	170	12	some	some	DET
eurjchem-788	170	13	carbonyl	carbonyl	NOUN
eurjchem-788	170	14	derivatives	derivative	NOUN
eurjchem-788	170	15	containing	contain	VERB
eurjchem-788	170	16	a	a	DET
eurjchem-788	170	17	reactive	reactive	ADJ
eurjchem-788	170	18	α‐methylene	α‐methylene	NUM
eurjchem-788	170	19	group	group	NOUN
eurjchem-788	170	20	were	be	AUX
eurjchem-788	170	21	depicted	depict	VERB
eurjchem-788	170	22	outline	outline	NOUN
eurjchem-788	170	23	.	.	PUNCT
eurjchem-788	171	1	the	the	DET
eurjchem-788	171	2	starting	start	VERB
eurjchem-788	171	3	material	material	NOUN
eurjchem-788	171	4	2‐aminothiophene‐3‐carbonitrile	2‐aminothiophene‐3‐carbonitrile	ADJ
eurjchem-788	171	5	1	1	NUM
eurjchem-788	171	6	was	be	AUX
eurjchem-788	171	7	prepared	prepare	VERB
eurjchem-788	171	8	in	in	ADP
eurjchem-788	171	9	one	one	NUM
eurjchem-788	171	10	step	step	NOUN
eurjchem-788	171	11	from	from	ADP
eurjchem-788	171	12	corresponding	correspond	VERB
eurjchem-788	171	13	ketones	ketone	NOUN
eurjchem-788	171	14	by	by	ADP
eurjchem-788	171	15	using	use	VERB
eurjchem-788	171	16	versatile	versatile	ADJ
eurjchem-788	171	17	gewald	gewald	NOUN
eurjchem-788	171	18	reaction	reaction	NOUN
eurjchem-788	171	19	[	[	X
eurjchem-788	171	20	16,17	16,17	NUM
eurjchem-788	171	21	]	]	PUNCT
eurjchem-788	171	22	(	(	PUNCT
eurjchem-788	171	23	scheme	scheme	NOUN
eurjchem-788	171	24	1	1	NUM
eurjchem-788	171	25	)	)	PUNCT
eurjchem-788	171	26	.	.	PUNCT
eurjchem-788	172	1	the	the	DET
eurjchem-788	172	2	synthesis	synthesis	NOUN
eurjchem-788	172	3	of	of	ADP
eurjchem-788	172	4	the	the	DET
eurjchem-788	172	5	4‐aminothienoquinolinones	4‐aminothienoquinolinone	NOUN
eurjchem-788	172	6	2	2	NUM
eurjchem-788	172	7	and	and	CCONJ
eurjchem-788	172	8	thienotacrine	thienotacrine	NOUN
eurjchem-788	172	9	3	3	NUM
eurjchem-788	172	10	were	be	AUX
eurjchem-788	172	11	performed	perform	VERB
eurjchem-788	172	12	by	by	ADP
eurjchem-788	172	13	using	use	VERB
eurjchem-788	172	14	friedländer	friedländ	ADJ
eurjchem-788	172	15	reaction	reaction	NOUN
eurjchem-788	172	16	.	.	PUNCT
eurjchem-788	173	1	precursor	precursor	NOUN
eurjchem-788	173	2	1	1	NUM
eurjchem-788	173	3	reacted	react	VERB
eurjchem-788	173	4	with	with	ADP
eurjchem-788	173	5	β‐dicarbonyl	β‐dicarbonyl	PUNCT
eurjchem-788	173	6	compounds	compound	NOUN
eurjchem-788	173	7	or	or	CCONJ
eurjchem-788	173	8	cyclohexanone	cyclohexanone	NOUN
eurjchem-788	173	9	under	under	ADP
eurjchem-788	173	10	conditions	condition	NOUN
eurjchem-788	173	11	i	i	PRON
eurjchem-788	173	12	)	)	PUNCT
eurjchem-788	173	13	or	or	CCONJ
eurjchem-788	173	14	ii	ii	X
eurjchem-788	173	15	)	)	PUNCT
eurjchem-788	173	16	to	to	PART
eurjchem-788	173	17	give	give	VERB
eurjchem-788	173	18	respectively	respectively	ADV
eurjchem-788	173	19	products	product	NOUN
eurjchem-788	173	20	2	2	NUM
eurjchem-788	173	21	and	and	CCONJ
eurjchem-788	173	22	3	3	NUM
eurjchem-788	173	23	(	(	PUNCT
eurjchem-788	173	24	scheme	scheme	NOUN
eurjchem-788	173	25	2	2	NUM
eurjchem-788	173	26	)	)	PUNCT
eurjchem-788	173	27	.	.	PUNCT
eurjchem-788	174	1	the	the	DET
eurjchem-788	174	2	remarkable	remarkable	ADJ
eurjchem-788	174	3	utility	utility	NOUN
eurjchem-788	174	4	of	of	ADP
eurjchem-788	174	5	clays	clay	NOUN
eurjchem-788	174	6	in	in	ADP
eurjchem-788	174	7	various	various	ADJ
eurjchem-788	174	8	reported	report	VERB
eurjchem-788	174	9	organic	organic	ADJ
eurjchem-788	174	10	transformations	transformation	NOUN
eurjchem-788	174	11	,	,	PUNCT
eurjchem-788	174	12	motivated	motivate	VERB
eurjchem-788	174	13	us	we	PRON
eurjchem-788	174	14	to	to	PART
eurjchem-788	174	15	initially	initially	ADV
eurjchem-788	174	16	test	test	VERB
eurjchem-788	174	17	the	the	DET
eurjchem-788	174	18	use	use	NOUN
eurjchem-788	174	19	of	of	ADP
eurjchem-788	174	20	acid	acid	ADJ
eurjchem-788	174	21	activated	activate	VERB
eurjchem-788	174	22	bentonite	bentonite	NOUN
eurjchem-788	174	23	as	as	ADP
eurjchem-788	174	24	catalyst	catalyst	NOUN
eurjchem-788	174	25	in	in	ADP
eurjchem-788	174	26	this	this	DET
eurjchem-788	174	27	field	field	NOUN
eurjchem-788	174	28	of	of	ADP
eurjchem-788	174	29	reaction	reaction	NOUN
eurjchem-788	174	30	.	.	PUNCT
eurjchem-788	175	1	in	in	ADP
eurjchem-788	175	2	fact	fact	NOUN
eurjchem-788	175	3	,	,	PUNCT
eurjchem-788	175	4	we	we	PRON
eurjchem-788	175	5	found	find	VERB
eurjchem-788	175	6	that	that	SCONJ
eurjchem-788	175	7	the	the	DET
eurjchem-788	175	8	use	use	NOUN
eurjchem-788	175	9	of	of	ADP
eurjchem-788	175	10	1000	1000	NUM
eurjchem-788	175	11	mg	mg	NOUN
eurjchem-788	175	12	activated	activate	VERB
eurjchem-788	175	13	bentonite	bentonite	NOUN
eurjchem-788	175	14	for	for	ADP
eurjchem-788	175	15	10	10	NUM
eurjchem-788	175	16	mmol	mmol	NOUN
eurjchem-788	175	17	of	of	ADP
eurjchem-788	175	18	cyclohexanone	cyclohexanone	PROPN
eurjchem-788	175	19	(	(	PUNCT
eurjchem-788	175	20	or	or	CCONJ
eurjchem-788	175	21	diketone	diketone	NOUN
eurjchem-788	175	22	)	)	PUNCT
eurjchem-788	175	23	under	under	ADP
eurjchem-788	175	24	dichloroethane	dichloroethane	ADJ
eurjchem-788	175	25	reflux	reflux	NOUN
eurjchem-788	175	26	for	for	ADP
eurjchem-788	175	27	24	24	NUM
eurjchem-788	175	28	hours	hour	NOUN
eurjchem-788	175	29	afforded	afford	VERB
eurjchem-788	175	30	thienotacrine	thienotacrine	NOUN
eurjchem-788	175	31	3	3	NUM
eurjchem-788	175	32	(	(	PUNCT
eurjchem-788	175	33	or	or	CCONJ
eurjchem-788	175	34	thienoquinolinone	thienoquinolinone	NOUN
eurjchem-788	175	35	2	2	NUM
eurjchem-788	175	36	)	)	PUNCT
eurjchem-788	175	37	in	in	ADP
eurjchem-788	175	38	high	high	ADJ
eurjchem-788	175	39	to	to	ADP
eurjchem-788	175	40	good	good	ADJ
eurjchem-788	175	41	yield	yield	NOUN
eurjchem-788	175	42	as	as	SCONJ
eurjchem-788	175	43	depicted	depict	VERB
eurjchem-788	175	44	in	in	ADP
eurjchem-788	175	45	table	table	NOUN
eurjchem-788	175	46	1	1	NUM
eurjchem-788	175	47	.	.	PUNCT
eurjchem-788	176	1	however	however	ADV
eurjchem-788	176	2	,	,	PUNCT
eurjchem-788	176	3	attempts	attempt	VERB
eurjchem-788	176	4	to	to	PART
eurjchem-788	176	5	use	use	VERB
eurjchem-788	176	6	a	a	DET
eurjchem-788	176	7	superstoichiometric	superstoichiometric	ADJ
eurjchem-788	176	8	amount	amount	NOUN
eurjchem-788	176	9	of	of	ADP
eurjchem-788	176	10	aluminium	aluminium	NOUN
eurjchem-788	176	11	chloride	chloride	NOUN
eurjchem-788	176	12	(	(	PUNCT
eurjchem-788	176	13	4	4	NUM
eurjchem-788	176	14	or	or	CCONJ
eurjchem-788	176	15	5	5	NUM
eurjchem-788	176	16	equiv	equiv	NOUN
eurjchem-788	176	17	.	.	PUNCT
eurjchem-788	176	18	)	)	PUNCT
eurjchem-788	176	19	led	lead	VERB
eurjchem-788	176	20	to	to	ADP
eurjchem-788	176	21	lower	low	ADJ
eurjchem-788	176	22	yield	yield	NOUN
eurjchem-788	176	23	.	.	PUNCT
eurjchem-788	177	1	the	the	DET
eurjchem-788	177	2	excellent	excellent	ADJ
eurjchem-788	177	3	result	result	NOUN
eurjchem-788	177	4	achieved	achieve	VERB
eurjchem-788	177	5	using	use	VERB
eurjchem-788	177	6	acid	acid	NOUN
eurjchem-788	177	7	activated	activate	VERB
eurjchem-788	177	8	bentonite	bentonite	NOUN
eurjchem-788	177	9	could	could	AUX
eurjchem-788	177	10	be	be	AUX
eurjchem-788	177	11	probably	probably	ADV
eurjchem-788	177	12	explained	explain	VERB
eurjchem-788	177	13	by	by	ADP
eurjchem-788	177	14	high	high	ADJ
eurjchem-788	177	15	absorptive	absorptive	ADJ
eurjchem-788	177	16	capacity	capacity	NOUN
eurjchem-788	177	17	and	and	CCONJ
eurjchem-788	177	18	the	the	DET
eurjchem-788	177	19	efficient	efficient	ADJ
eurjchem-788	177	20	coordination	coordination	NOUN
eurjchem-788	177	21	of	of	ADP
eurjchem-788	177	22	catalyst	catalyst	NOUN
eurjchem-788	177	23	and	and	CCONJ
eurjchem-788	177	24	reactants	reactant	NOUN
eurjchem-788	177	25	.	.	PUNCT
eurjchem-788	178	1	4	4	X
eurjchem-788	178	2	.	.	X
eurjchem-788	178	3	conclusion	conclusion	NOUN
eurjchem-788	178	4	in	in	ADP
eurjchem-788	178	5	order	order	NOUN
eurjchem-788	178	6	to	to	PART
eurjchem-788	178	7	investigate	investigate	VERB
eurjchem-788	178	8	the	the	DET
eurjchem-788	178	9	biological	biological	ADJ
eurjchem-788	178	10	effects	effect	NOUN
eurjchem-788	178	11	of	of	ADP
eurjchem-788	178	12	structural	structural	ADJ
eurjchem-788	178	13	modification	modification	NOUN
eurjchem-788	178	14	of	of	ADP
eurjchem-788	178	15	tacrine	tacrine	NOUN
eurjchem-788	178	16	,	,	PUNCT
eurjchem-788	178	17	a	a	DET
eurjchem-788	178	18	simple	simple	ADJ
eurjchem-788	178	19	and	and	CCONJ
eurjchem-788	178	20	green	green	ADJ
eurjchem-788	178	21	one‐pot	one‐pot	NOUN
eurjchem-788	178	22	process	process	NOUN
eurjchem-788	178	23	was	be	AUX
eurjchem-788	178	24	developed	develop	VERB
eurjchem-788	178	25	for	for	ADP
eurjchem-788	178	26	the	the	DET
eurjchem-788	178	27	synthesis	synthesis	NOUN
eurjchem-788	178	28	of	of	ADP
eurjchem-788	178	29	4‐aminothienoquinolinones	4‐aminothienoquinolinone	NOUN
eurjchem-788	178	30	2	2	NUM
eurjchem-788	178	31	and	and	CCONJ
eurjchem-788	178	32	thienotacrine	thienotacrine	VERB
eurjchem-788	178	33	3	3	NUM
eurjchem-788	178	34	derivatives	derivative	NOUN
eurjchem-788	178	35	via	via	ADP
eurjchem-788	178	36	friedländer	friedländer	NOUN
eurjchem-788	178	37	condensation	condensation	NOUN
eurjchem-788	178	38	reaction	reaction	NOUN
eurjchem-788	178	39	promoted	promote	VERB
eurjchem-788	178	40	by	by	ADP
eurjchem-788	178	41	an	an	DET
eurjchem-788	178	42	environmentally	environmentally	ADV
eurjchem-788	178	43	friendly	friendly	ADJ
eurjchem-788	178	44	catalyst	catalyst	NOUN
eurjchem-788	178	45	such	such	ADJ
eurjchem-788	178	46	as	as	ADP
eurjchem-788	178	47	bentonite	bentonite	NOUN
eurjchem-788	178	48	.	.	PUNCT
eurjchem-788	179	1	acknowledgements	acknowledgement	NOUN
eurjchem-788	179	2	the	the	DET
eurjchem-788	179	3	authors	author	NOUN
eurjchem-788	179	4	extend	extend	VERB
eurjchem-788	179	5	their	their	PRON
eurjchem-788	179	6	appreciation	appreciation	NOUN
eurjchem-788	179	7	to	to	ADP
eurjchem-788	179	8	the	the	DET
eurjchem-788	179	9	deanship	deanship	NOUN
eurjchem-788	179	10	of	of	ADP
eurjchem-788	179	11	scientific	scientific	ADJ
eurjchem-788	179	12	research	research	NOUN
eurjchem-788	179	13	at	at	ADP
eurjchem-788	179	14	qassim	qassim	PROPN
eurjchem-788	179	15	university	university	PROPN
eurjchem-788	179	16	for	for	ADP
eurjchem-788	179	17	the	the	DET
eurjchem-788	179	18	financial	financial	ADJ
eurjchem-788	179	19	support	support	NOUN
eurjchem-788	179	20	of	of	ADP
eurjchem-788	179	21	this	this	DET
eurjchem-788	179	22	work	work	NOUN
eurjchem-788	179	23	(	(	PUNCT
eurjchem-788	179	24	project	project	NOUN
eurjchem-788	179	25	no	no	PRON
eurjchem-788	179	26	:	:	PUNCT
eurjchem-788	179	27	1799	1799	NUM
eurjchem-788	179	28	)	)	PUNCT
eurjchem-788	179	29	.	.	PUNCT
eurjchem-788	180	1	references	reference	NOUN
eurjchem-788	180	2	[	[	X
eurjchem-788	180	3	1	1	NUM
eurjchem-788	180	4	]	]	PUNCT
eurjchem-788	180	5	.	.	PUNCT
eurjchem-788	181	1	summers	summer	NOUN
eurjchem-788	181	2	,	,	PUNCT
eurjchem-788	181	3	w.	w.	PROPN
eurjchem-788	181	4	k.	k.	PROPN
eurjchem-788	181	5	;	;	PUNCT
eurjchem-788	181	6	majovsky	majovsky	PROPN
eurjchem-788	181	7	,	,	PUNCT
eurjchem-788	181	8	l.	l.	PROPN
eurjchem-788	181	9	v.	v.	PROPN
eurjchem-788	181	10	;	;	PUNCT
eurjchem-788	181	11	marsh	marsh	PROPN
eurjchem-788	181	12	,	,	PUNCT
eurjchem-788	181	13	g.	g.	PROPN
eurjchem-788	181	14	m.	m.	PROPN
eurjchem-788	181	15	;	;	PUNCT
eurjchem-788	181	16	tachiki	tachiki	PROPN
eurjchem-788	181	17	,	,	PUNCT
eurjchem-788	181	18	k.	k.	PROPN
eurjchem-788	181	19	;	;	PUNCT
eurjchem-788	181	20	kling	kling	PROPN
eurjchem-788	181	21	,	,	PUNCT
eurjchem-788	181	22	a.	a.	PROPN
eurjchem-788	181	23	n.	n.	PROPN
eurjchem-788	181	24	engl	engl	PROPN
eurjchem-788	181	25	.	.	PUNCT
eurjchem-788	182	1	j.	j.	PROPN
eurjchem-788	182	2	med	med	PROPN
eurjchem-788	182	3	.	.	PROPN
eurjchem-788	182	4	1986	1986	NUM
eurjchem-788	182	5	,	,	PUNCT
eurjchem-788	182	6	315	315	NUM
eurjchem-788	182	7	,	,	PUNCT
eurjchem-788	182	8	1241‐1287	1241‐1287	NUM
eurjchem-788	183	1	[	[	X
eurjchem-788	183	2	2	2	NUM
eurjchem-788	183	3	]	]	PUNCT
eurjchem-788	183	4	.	.	PUNCT
eurjchem-788	184	1	sahakian	sahakian	PROPN
eurjchem-788	184	2	,	,	PUNCT
eurjchem-788	184	3	b.	b.	PROPN
eurjchem-788	184	4	j.	j.	PROPN
eurjchem-788	184	5	;	;	PUNCT
eurjchem-788	184	6	owen	owen	PROPN
eurjchem-788	184	7	,	,	PUNCT
eurjchem-788	184	8	a.	a.	NOUN
eurjchem-788	184	9	m.	m.	NOUN
eurjchem-788	184	10	;	;	PUNCT
eurjchem-788	184	11	morant	morant	PROPN
eurjchem-788	184	12	,	,	PUNCT
eurjchem-788	184	13	n.	n.	PROPN
eurjchem-788	184	14	j.	j.	PROPN
eurjchem-788	184	15	;	;	PUNCT
eurjchem-788	184	16	eagger	eagger	ADJ
eurjchem-788	184	17	,	,	PUNCT
eurjchem-788	184	18	s.	s.	PROPN
eurjchem-788	184	19	a.	a.	PROPN
eurjchem-788	184	20	;	;	PUNCT
eurjchem-788	184	21	boddington	boddington	PROPN
eurjchem-788	184	22	,	,	PUNCT
eurjchem-788	184	23	s.	s.	PROPN
eurjchem-788	184	24	;	;	PUNCT
eurjchem-788	184	25	crayton	crayton	PROPN
eurjchem-788	184	26	,	,	PUNCT
eurjchem-788	184	27	l.	l.	PROPN
eurjchem-788	184	28	;	;	PUNCT
eurjchem-788	184	29	crockford	crockford	PROPN
eurjchem-788	184	30	,	,	PUNCT
eurjchem-788	184	31	h.	h.	PROPN
eurjchem-788	184	32	a.	a.	PROPN
eurjchem-788	184	33	;	;	PUNCT
eurjchem-788	184	34	crooks	crook	NOUN
eurjchem-788	184	35	,	,	PUNCT
eurjchem-788	184	36	m.	m.	NOUN
eurjchem-788	184	37	;	;	PUNCT
eurjchem-788	184	38	hill	hill	PROPN
eurjchem-788	184	39	,	,	PUNCT
eurjchem-788	184	40	k.	k.	PROPN
eurjchem-788	184	41	;	;	PUNCT
eurjchem-788	184	42	levy	levy	NOUN
eurjchem-788	184	43	,	,	PUNCT
eurjchem-788	184	44	r.	r.	PROPN
eurjchem-788	184	45	psychopharmacology	psychopharmacology	PROPN
eurjchem-788	184	46	1993	1993	NUM
eurjchem-788	184	47	,	,	PUNCT
eurjchem-788	184	48	110	110	NUM
eurjchem-788	184	49	,	,	PUNCT
eurjchem-788	184	50	395‐401	395‐401	NUM
eurjchem-788	184	51	.	.	PUNCT
eurjchem-788	185	1	[	[	X
eurjchem-788	185	2	3	3	NUM
eurjchem-788	185	3	]	]	PUNCT
eurjchem-788	185	4	.	.	PUNCT
eurjchem-788	186	1	drukarch	drukarch	NOUN
eurjchem-788	186	2	,	,	PUNCT
eurjchem-788	186	3	b.	b.	PROPN
eurjchem-788	186	4	;	;	PUNCT
eurjchem-788	186	5	kits	kits	PROPN
eurjchem-788	186	6	,	,	PUNCT
eurjchem-788	186	7	k.	k.	PROPN
eurjchem-788	186	8	s.	s.	PROPN
eurjchem-788	186	9	;	;	PUNCT
eurjchem-788	186	10	van	van	PROPN
eurjchem-788	186	11	der	der	PROPN
eurjchem-788	186	12	meer	meer	PROPN
eurjchem-788	186	13	,	,	PUNCT
eurjchem-788	186	14	e.	e.	PROPN
eurjchem-788	186	15	g.	g.	PROPN
eurjchem-788	186	16	;	;	PUNCT
eurjchem-788	186	17	lodder	lodder	PROPN
eurjchem-788	186	18	,	,	PUNCT
eurjchem-788	186	19	j.	j.	PROPN
eurjchem-788	186	20	c.	c.	PROPN
eurjchem-788	186	21	;	;	PUNCT
eurjchem-788	186	22	stoof	stoof	PROPN
eurjchem-788	186	23	,	,	PUNCT
eurjchem-788	186	24	j.	j.	PROPN
eurjchem-788	186	25	c.	c.	PROPN
eurjchem-788	186	26	eur	eur	PROPN
eurjchem-788	186	27	.	.	PUNCT
eurjchem-788	187	1	j.	j.	PROPN
eurjchem-788	187	2	pharmacol	pharmacol	PROPN
eurjchem-788	187	3	.	.	PUNCT
eurjchem-788	188	1	1987	1987	NUM
eurjchem-788	188	2	,	,	PUNCT
eurjchem-788	188	3	141	141	NUM
eurjchem-788	188	4	,	,	PUNCT
eurjchem-788	188	5	153‐157	153‐157	NUM
eurjchem-788	188	6	.	.	PUNCT
eurjchem-788	189	1	[	[	X
eurjchem-788	189	2	4	4	NUM
eurjchem-788	189	3	]	]	PUNCT
eurjchem-788	189	4	.	.	PUNCT
eurjchem-788	190	1	augry	augry	PROPN
eurjchem-788	190	2	,	,	PUNCT
eurjchem-788	190	3	f.	f.	PROPN
eurjchem-788	190	4	;	;	PUNCT
eurjchem-788	190	5	darch	darch	PROPN
eurjchem-788	190	6	,	,	PUNCT
eurjchem-788	190	7	a.	a.	NOUN
eurjchem-788	190	8	;	;	PUNCT
eurjchem-788	190	9	de	de	PROPN
eurjchem-788	190	10	routou	routou	PROPN
eurjchem-788	190	11	,	,	PUNCT
eurjchem-788	190	12	j.	j.	PROPN
eurjchem-788	190	13	;	;	PUNCT
eurjchem-788	190	14	guelfi	guelfi	NOUN
eurjchem-788	190	15	,	,	PUNCT
eurjchem-788	190	16	m.	m.	NOUN
eurjchem-788	190	17	c.	c.	PROPN
eurjchem-788	190	18	;	;	PUNCT
eurjchem-788	190	19	forette	forette	PROPN
eurjchem-788	190	20	,	,	PUNCT
eurjchem-788	190	21	f.	f.	PROPN
eurjchem-788	190	22	j.	j.	PROPN
eurjchem-788	190	23	pharm	pharm	PROPN
eurjchem-788	190	24	.	.	PUNCT
eurjchem-788	191	1	clin	clin	PROPN
eurjchem-788	191	2	.	.	PUNCT
eurjchem-788	192	1	1997	1997	NUM
eurjchem-788	192	2	,	,	PUNCT
eurjchem-788	192	3	16	16	NUM
eurjchem-788	192	4	,	,	PUNCT
eurjchem-788	192	5	183‐201	183‐201	NUM
eurjchem-788	192	6	.	.	PUNCT
eurjchem-788	193	1	[	[	X
eurjchem-788	193	2	5	5	NUM
eurjchem-788	193	3	]	]	PUNCT
eurjchem-788	193	4	.	.	PUNCT
eurjchem-788	193	5	dridi	dridi	PROPN
eurjchem-788	193	6	,	,	PUNCT
eurjchem-788	193	7	k.	k.	PROPN
eurjchem-788	193	8	;	;	PUNCT
eurjchem-788	193	9	el	el	PROPN
eurjchem-788	193	10	efrit	efrit	PROPN
eurjchem-788	193	11	,	,	PUNCT
eurjchem-788	193	12	m.	m.	PROPN
eurjchem-788	193	13	l.	l.	PROPN
eurjchem-788	193	14	;	;	PUNCT
eurjchem-788	193	15	zantour	zantour	PROPN
eurjchem-788	193	16	,	,	PUNCT
eurjchem-788	193	17	h.	h.	PROPN
eurjchem-788	193	18	j.	j.	PROPN
eurjchem-788	193	19	soc	soc	PROPN
eurjchem-788	193	20	.	.	PUNCT
eurjchem-788	194	1	chim	chim	PROPN
eurjchem-788	194	2	.	.	PUNCT
eurjchem-788	195	1	tunisie	tunisie	PROPN
eurjchem-788	195	2	1999	1999	NUM
eurjchem-788	195	3	,	,	PUNCT
eurjchem-788	195	4	5	5	NUM
eurjchem-788	195	5	,	,	PUNCT
eurjchem-788	195	6	387‐	387‐	NUM
eurjchem-788	195	7	392	392	NUM
eurjchem-788	195	8	.	.	PUNCT
eurjchem-788	196	1	[	[	X
eurjchem-788	196	2	6	6	NUM
eurjchem-788	196	3	]	]	PUNCT
eurjchem-788	196	4	.	.	PUNCT
eurjchem-788	196	5	dridi	dridi	PROPN
eurjchem-788	196	6	,	,	PUNCT
eurjchem-788	196	7	k.	k.	PROPN
eurjchem-788	196	8	;	;	PUNCT
eurjchem-788	196	9	el	el	PROPN
eurjchem-788	196	10	efrit	efrit	PROPN
eurjchem-788	196	11	,	,	PUNCT
eurjchem-788	196	12	m.	m.	PROPN
eurjchem-788	196	13	l.	l.	PROPN
eurjchem-788	196	14	;	;	PUNCT
eurjchem-788	196	15	zantour	zantour	PROPN
eurjchem-788	196	16	,	,	PUNCT
eurjchem-788	196	17	h.	h.	PROPN
eurjchem-788	196	18	j.	j.	PROPN
eurjchem-788	196	19	soc	soc	PROPN
eurjchem-788	196	20	.	.	PUNCT
eurjchem-788	197	1	chim	chim	PROPN
eurjchem-788	197	2	.	.	PUNCT
eurjchem-788	198	1	tunisie	tunisie	PROPN
eurjchem-788	198	2	2001	2001	NUM
eurjchem-788	198	3	,	,	PUNCT
eurjchem-788	198	4	4	4	NUM
eurjchem-788	198	5	,	,	PUNCT
eurjchem-788	198	6	957‐	957‐	NUM
eurjchem-788	198	7	963	963	NUM
eurjchem-788	198	8	.	.	PUNCT
eurjchem-788	199	1	[	[	X
eurjchem-788	199	2	7	7	NUM
eurjchem-788	199	3	]	]	PUNCT
eurjchem-788	199	4	.	.	PUNCT
eurjchem-788	199	5	gutschow	gutschow	NOUN
eurjchem-788	199	6	,	,	PUNCT
eurjchem-788	199	7	m.	m.	NOUN
eurjchem-788	199	8	;	;	PUNCT
eurjchem-788	199	9	kuerschner	kuerschner	ADV
eurjchem-788	199	10	,	,	PUNCT
eurjchem-788	199	11	l.	l.	PROPN
eurjchem-788	199	12	;	;	PUNCT
eurjchem-788	199	13	neumann	neumann	PROPN
eurjchem-788	199	14	,	,	PUNCT
eurjchem-788	199	15	u.	u.	PROPN
eurjchem-788	199	16	;	;	PUNCT
eurjchem-788	199	17	peitsch	peitsch	NOUN
eurjchem-788	199	18	,	,	PUNCT
eurjchem-788	199	19	m.	m.	NOUN
eurjchem-788	199	20	;	;	PUNCT
eurjchem-788	199	21	loser	loser	PROPN
eurjchem-788	199	22	,	,	PUNCT
eurjchem-788	199	23	r.	r.	PROPN
eurjchem-788	199	24	;	;	PUNCT
eurjchem-788	199	25	koglin	koglin	PROPN
eurjchem-788	199	26	,	,	PUNCT
eurjchem-788	199	27	n.	n.	NOUN
eurjchem-788	199	28	;	;	PUNCT
eurjchem-788	199	29	eger	eger	PROPN
eurjchem-788	199	30	,	,	PUNCT
eurjchem-788	199	31	k.	k.	PROPN
eurjchem-788	199	32	j.	j.	PROPN
eurjchem-788	199	33	med	med	PROPN
eurjchem-788	199	34	.	.	PROPN
eurjchem-788	199	35	chem	chem	PROPN
eurjchem-788	199	36	.	.	PUNCT
eurjchem-788	200	1	1999	1999	NUM
eurjchem-788	200	2	,	,	PUNCT
eurjchem-788	200	3	42	42	NUM
eurjchem-788	200	4	,	,	PUNCT
eurjchem-788	200	5	5437‐5447	5437‐5447	NUM
eurjchem-788	200	6	.	.	PUNCT
eurjchem-788	201	1	[	[	X
eurjchem-788	201	2	8	8	NUM
eurjchem-788	201	3	]	]	PUNCT
eurjchem-788	201	4	.	.	PUNCT
eurjchem-788	202	1	fugita	fugita	NOUN
eurjchem-788	202	2	,	,	PUNCT
eurjchem-788	202	3	m.	m.	NOUN
eurjchem-788	202	4	;	;	PUNCT
eurjchem-788	202	5	seki	seki	PROPN
eurjchem-788	202	6	,	,	PUNCT
eurjchem-788	202	7	t.	t.	PROPN
eurjchem-788	202	8	;	;	PUNCT
eurjchem-788	202	9	ikeda	ikeda	PROPN
eurjchem-788	202	10	,	,	PUNCT
eurjchem-788	202	11	n.	n.	NOUN
eurjchem-788	202	12	bioorg	bioorg	PROPN
eurjchem-788	202	13	.	.	PUNCT
eurjchem-788	203	1	med	med	PROPN
eurjchem-788	203	2	.	.	PROPN
eurjchem-788	203	3	chem	chem	PROPN
eurjchem-788	203	4	.	.	PUNCT
eurjchem-788	204	1	lett	lett	PROPN
eurjchem-788	204	2	.	.	PUNCT
eurjchem-788	205	1	2002	2002	NUM
eurjchem-788	205	2	,	,	PUNCT
eurjchem-788	205	3	12	12	NUM
eurjchem-788	205	4	,	,	PUNCT
eurjchem-788	205	5	1897‐	1897‐	NUM
eurjchem-788	205	6	1900	1900	NUM
eurjchem-788	205	7	.	.	PUNCT
eurjchem-788	206	1	[	[	X
eurjchem-788	206	2	9	9	NUM
eurjchem-788	206	3	]	]	PUNCT
eurjchem-788	206	4	.	.	PUNCT
eurjchem-788	207	1	harza	harza	PROPN
eurjchem-788	207	2	,	,	PUNCT
eurjchem-788	207	3	k.	k.	PROPN
eurjchem-788	207	4	;	;	PUNCT
eurjchem-788	207	5	saravanan	saravanan	PROPN
eurjchem-788	207	6	,	,	PUNCT
eurjchem-788	207	7	j.	j.	PROPN
eurjchem-788	207	8	;	;	PUNCT
eurjchem-788	207	9	mohan	mohan	PROPN
eurjchem-788	207	10	,	,	PUNCT
eurjchem-788	207	11	s.	s.	PROPN
eurjchem-788	207	12	asian	asian	PROPN
eurjchem-788	207	13	j.	j.	PROPN
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eurjchem-788	207	15	.	.	PUNCT
eurjchem-788	208	1	2007	2007	NUM
eurjchem-788	208	2	,	,	PUNCT
eurjchem-788	208	3	19	19	NUM
eurjchem-788	208	4	,	,	PUNCT
eurjchem-788	208	5	3541‐3544	3541‐3544	NUM
eurjchem-788	208	6	.	.	PUNCT
eurjchem-788	209	1	[	[	X
eurjchem-788	209	2	10	10	NUM
eurjchem-788	209	3	]	]	PUNCT
eurjchem-788	209	4	.	.	PUNCT
eurjchem-788	210	1	narlawar	narlawar	PROPN
eurjchem-788	210	2	,	,	PUNCT
eurjchem-788	210	3	r.	r.	PROPN
eurjchem-788	210	4	;	;	PUNCT
eurjchem-788	210	5	lane	lane	PROPN
eurjchem-788	210	6	,	,	PUNCT
eurjchem-788	210	7	j.	j.	PROPN
eurjchem-788	210	8	r.	r.	PROPN
eurjchem-788	210	9	;	;	PUNCT
eurjchem-788	210	10	doddareddy	doddareddy	ADJ
eurjchem-788	210	11	,	,	PUNCT
eurjchem-788	210	12	m.	m.	NOUN
eurjchem-788	210	13	;	;	PUNCT
eurjchem-788	210	14	lin	lin	PROPN
eurjchem-788	210	15	,	,	PUNCT
eurjchem-788	210	16	j.	j.	PROPN
eurjchem-788	210	17	;	;	PUNCT
eurjchem-788	210	18	brussee	brussee	PROPN
eurjchem-788	210	19	,	,	PUNCT
eurjchem-788	210	20	j.	j.	PROPN
eurjchem-788	210	21	;	;	PUNCT
eurjchem-788	210	22	ijzerman	ijzerman	PROPN
eurjchem-788	210	23	,	,	PUNCT
eurjchem-788	211	1	a.	a.	PROPN
eurjchem-788	211	2	p.	p.	PROPN
eurjchem-788	211	3	j.	j.	PROPN
eurjchem-788	211	4	med	med	PROPN
eurjchem-788	211	5	.	.	PROPN
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eurjchem-788	211	7	.	.	PUNCT
eurjchem-788	212	1	2010	2010	NUM
eurjchem-788	212	2	,	,	PUNCT
eurjchem-788	212	3	53	53	NUM
eurjchem-788	212	4	,	,	PUNCT
eurjchem-788	212	5	3028‐3037	3028‐3037	NUM
eurjchem-788	212	6	.	.	PUNCT
eurjchem-788	213	1	[	[	X
eurjchem-788	213	2	11	11	NUM
eurjchem-788	213	3	]	]	PUNCT
eurjchem-788	213	4	.	.	PUNCT
eurjchem-788	214	1	marco‐contelles	marco‐contelle	NOUN
eurjchem-788	214	2	,	,	PUNCT
eurjchem-788	214	3	j.	j.	PROPN
eurjchem-788	214	4	;	;	PUNCT
eurjchem-788	214	5	perez‐mayoral	perez‐mayoral	PROPN
eurjchem-788	214	6	,	,	PUNCT
eurjchem-788	214	7	e.	e.	PROPN
eurjchem-788	214	8	;	;	PUNCT
eurjchem-788	214	9	samadi	samadi	NOUN
eurjchem-788	214	10	,	,	PUNCT
eurjchem-788	214	11	a.	a.	NOUN
eurjchem-788	214	12	;	;	PUNCT
eurjchem-788	214	13	carreiras	carreira	NOUN
eurjchem-788	214	14	,	,	PUNCT
eurjchem-788	214	15	m.	m.	PROPN
eurjchem-788	214	16	c.	c.	PROPN
eurjchem-788	214	17	;	;	PUNCT
eurjchem-788	214	18	soriano	soriano	PROPN
eurjchem-788	214	19	,	,	PUNCT
eurjchem-788	214	20	e.	e.	PROPN
eurjchem-788	214	21	chem	chem	PROPN
eurjchem-788	214	22	.	.	PUNCT
eurjchem-788	215	1	rev	rev	PROPN
eurjchem-788	215	2	.	.	PROPN
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eurjchem-788	215	4	,	,	PUNCT
eurjchem-788	215	5	109	109	NUM
eurjchem-788	215	6	,	,	PUNCT
eurjchem-788	215	7	2652‐2671	2652‐2671	NUM
eurjchem-788	215	8	.	.	PUNCT
eurjchem-788	216	1	[	[	X
eurjchem-788	216	2	12	12	NUM
eurjchem-788	216	3	]	]	PUNCT
eurjchem-788	216	4	.	.	PUNCT
eurjchem-788	217	1	laszlo	laszlo	PROPN
eurjchem-788	217	2	,	,	PUNCT
eurjchem-788	217	3	p.	p.	NOUN
eurjchem-788	217	4	;	;	PUNCT
eurjchem-788	217	5	mathy	mathy	ADJ
eurjchem-788	217	6	,	,	PUNCT
eurjchem-788	217	7	a.	a.	PROPN
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eurjchem-788	217	9	.	.	PUNCT
eurjchem-788	218	1	chim	chim	PROPN
eurjchem-788	218	2	.	.	PUNCT
eurjchem-788	219	1	acta	acta	PROPN
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eurjchem-788	219	3	,	,	PUNCT
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eurjchem-788	219	5	,	,	PUNCT
eurjchem-788	219	6	577‐586	577‐586	NUM
eurjchem-788	219	7	.	.	PUNCT
eurjchem-788	220	1	[	[	X
eurjchem-788	220	2	13	13	NUM
eurjchem-788	220	3	]	]	PUNCT
eurjchem-788	220	4	.	.	PUNCT
eurjchem-788	221	1	choudary	choudary	PROPN
eurjchem-788	221	2	,	,	PUNCT
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eurjchem-788	221	5	;	;	PUNCT
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eurjchem-788	221	7	,	,	PUNCT
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eurjchem-788	221	10	;	;	PUNCT
eurjchem-788	221	11	rao	rao	PROPN
eurjchem-788	221	12	,	,	PUNCT
eurjchem-788	221	13	k.	k.	PROPN
eurjchem-788	221	14	k.	k.	PROPN
eurjchem-788	221	15	;	;	PUNCT
eurjchem-788	222	1	santhi	santhi	X
eurjchem-788	222	2	,	,	PUNCT
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eurjchem-788	222	4	l.	l.	PROPN
eurjchem-788	222	5	appl	appl	PROPN
eurjchem-788	222	6	.	.	PUNCT
eurjchem-788	223	1	catal	catal	PROPN
eurjchem-788	223	2	.	.	PUNCT
eurjchem-788	223	3	a.	a.	PROPN
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eurjchem-788	223	5	.	.	PROPN
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eurjchem-788	223	7	,	,	PUNCT
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eurjchem-788	223	9	,	,	PUNCT
eurjchem-788	223	10	257‐264	257‐264	NUM
eurjchem-788	223	11	.	.	PUNCT
eurjchem-788	224	1	[	[	X
eurjchem-788	224	2	14	14	NUM
eurjchem-788	224	3	]	]	SYM
eurjchem-788	224	4	.	.	PUNCT
eurjchem-788	225	1	yoo	yoo	PROPN
eurjchem-788	225	2	,	,	PUNCT
eurjchem-788	225	3	j.	j.	PROPN
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eurjchem-788	225	5	;	;	PUNCT
eurjchem-788	225	6	lee	lee	PROPN
eurjchem-788	225	7	,	,	PUNCT
eurjchem-788	225	8	c.	c.	PROPN
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eurjchem-788	225	10	;	;	PUNCT
eurjchem-788	225	11	jeong	jeong	PROPN
eurjchem-788	225	12	,	,	PUNCT
eurjchem-788	225	13	h.	h.	PROPN
eurjchem-788	225	14	c.	c.	PROPN
eurjchem-788	225	15	;	;	PUNCT
eurjchem-788	225	16	park	park	NOUN
eurjchem-788	225	17	,	,	PUNCT
eurjchem-788	225	18	y.	y.	PROPN
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eurjchem-788	225	20	;	;	PUNCT
eurjchem-788	225	21	park	park	PROPN
eurjchem-788	225	22	,	,	PUNCT
eurjchem-788	225	23	s.	s.	PROPN
eurjchem-788	225	24	e.	e.	PROPN
eurjchem-788	225	25	catal	catal	PROPN
eurjchem-788	225	26	.	.	PUNCT
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eurjchem-788	226	3	,	,	PUNCT
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eurjchem-788	226	5	,	,	PUNCT
eurjchem-788	226	6	255‐261	255‐261	NUM
eurjchem-788	226	7	.	.	PUNCT
eurjchem-788	227	1	[	[	X
eurjchem-788	227	2	15	15	NUM
eurjchem-788	227	3	]	]	PUNCT
eurjchem-788	227	4	.	.	PUNCT
eurjchem-788	228	1	inui	inui	PROPN
eurjchem-788	228	2	,	,	PUNCT
eurjchem-788	228	3	k.	k.	PROPN
eurjchem-788	228	4	;	;	PUNCT
eurjchem-788	228	5	kurabayashi	kurabayashi	PROPN
eurjchem-788	228	6	,	,	PUNCT
eurjchem-788	228	7	t.	t.	PROPN
eurjchem-788	228	8	;	;	PUNCT
eurjchem-788	228	9	sato	sato	PROPN
eurjchem-788	228	10	,	,	PUNCT
eurjchem-788	228	11	s.	s.	PROPN
eurjchem-788	228	12	;	;	PUNCT
eurjchem-788	228	13	ichikawa	ichikawa	PROPN
eurjchem-788	228	14	,	,	PUNCT
eurjchem-788	228	15	n.	n.	PROPN
eurjchem-788	228	16	j.	j.	PROPN
eurjchem-788	228	17	mol	mol	PROPN
eurjchem-788	228	18	.	.	PROPN
eurjchem-788	228	19	catal	catal	PROPN
eurjchem-788	228	20	.	.	PUNCT
eurjchem-788	229	1	a	a	DET
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eurjchem-788	229	3	,	,	PUNCT
eurjchem-788	229	4	216	216	NUM
eurjchem-788	229	5	,	,	PUNCT
eurjchem-788	229	6	147‐155	147‐155	NUM
eurjchem-788	229	7	.	.	PUNCT
eurjchem-788	230	1	[	[	X
eurjchem-788	230	2	16	16	NUM
eurjchem-788	230	3	]	]	PUNCT
eurjchem-788	230	4	.	.	PUNCT
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eurjchem-788	231	2	,	,	PUNCT
eurjchem-788	231	3	k.	k.	PROPN
eurjchem-788	231	4	;	;	PUNCT
eurjchem-788	231	5	schinke	schinke	PROPN
eurjchem-788	231	6	,	,	PUNCT
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eurjchem-788	231	8	;	;	PUNCT
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