id	sid	tid	token	lemma	pos
eurjchem-205	1	1	untitled	untitle	VERB
eurjchem-205	1	2	european	european	PROPN
eurjchem-205	1	3	journal	journal	PROPN
eurjchem-205	1	4	of	of	ADP
eurjchem-205	1	5	chemistry	chemistry	NOUN
eurjchem-205	1	6	2	2	NUM
eurjchem-205	1	7	(	(	PUNCT
eurjchem-205	1	8	2	2	NUM
eurjchem-205	1	9	)	)	PUNCT
eurjchem-205	1	10	(	(	PUNCT
eurjchem-205	1	11	2011	2011	NUM
eurjchem-205	1	12	)	)	PUNCT
eurjchem-205	1	13	235‐237	235‐237	NUM
eurjchem-205	1	14	european	european	PROPN
eurjchem-205	1	15	journal	journal	PROPN
eurjchem-205	1	16	of	of	ADP
eurjchem-205	1	17	chemistry	chemistry	NOUN
eurjchem-205	1	18	issn	issn	PROPN
eurjchem-205	1	19	2153‐2249	2153‐2249	PROPN
eurjchem-205	1	20	(	(	PUNCT
eurjchem-205	1	21	print	print	NOUN
eurjchem-205	1	22	)	)	PUNCT
eurjchem-205	1	23	/	/	SYM
eurjchem-205	1	24	issn	issn	PROPN
eurjchem-205	1	25	2153‐2257	2153‐2257	NUM
eurjchem-205	1	26	(	(	PUNCT
eurjchem-205	1	27	online	online	ADJ
eurjchem-205	1	28	)	)	PUNCT
eurjchem-205	1	29			NOUN
eurjchem-205	1	30	2011	2011	NUM
eurjchem-205	1	31	eurjchem	eurjchem	PROPN
eurjchem-205	1	32	doi:10.5155	doi:10.5155	PROPN
eurjchem-205	1	33	/	/	SYM
eurjchem-205	1	34	eurjchem.2.2.235‐237.205	eurjchem.2.2.235‐237.205	X
eurjchem-205	1	35	european	european	PROPN
eurjchem-205	1	36	journal	journal	PROPN
eurjchem-205	1	37	of	of	ADP
eurjchem-205	1	38	chemistry	chemistry	PROPN
eurjchem-205	1	39	journal	journal	PROPN
eurjchem-205	1	40	homepage	homepage	NOUN
eurjchem-205	1	41	:	:	PUNCT
eurjchem-205	1	42	www.eurjchem.com	www.eurjchem.com	X
eurjchem-205	1	43	an	an	DET
eurjchem-205	1	44	improved	improved	ADJ
eurjchem-205	1	45	synthesis	synthesis	NOUN
eurjchem-205	1	46	of	of	ADP
eurjchem-205	1	47	the	the	DET
eurjchem-205	1	48	alkaloid	alkaloid	PROPN
eurjchem-205	1	49	luotonin‐a	luotonin‐a	NOUN
eurjchem-205	1	50	employing	employ	VERB
eurjchem-205	1	51	ionic	ionic	ADJ
eurjchem-205	1	52	liquid	liquid	NOUN
eurjchem-205	1	53	and	and	CCONJ
eurjchem-205	1	54	water	water	NOUN
eurjchem-205	1	55	as	as	ADP
eurjchem-205	1	56	key	key	ADJ
eurjchem-205	1	57	solvents	solvent	NOUN
eurjchem-205	1	58	taterao	taterao	ADP
eurjchem-205	1	59	marutao	marutao	PROPN
eurjchem-205	1	60	potewara	potewara	PROPN
eurjchem-205	1	61	,	,	PUNCT
eurjchem-205	1	62	muthu	muthu	PROPN
eurjchem-205	1	63	kumaradoss	kumaradoss	ADJ
eurjchem-205	1	64	kathiravanb	kathiravanb	PROPN
eurjchem-205	1	65	,	,	PUNCT
eurjchem-205	1	66	aparna	aparna	PROPN
eurjchem-205	1	67	surendra	surendra	PROPN
eurjchem-205	1	68	chothec	chothec	PROPN
eurjchem-205	1	69	and	and	CCONJ
eurjchem-205	1	70	kumar	kumar	PROPN
eurjchem-205	1	71	venkatram	venkatram	PROPN
eurjchem-205	1	72	srinivasana	srinivasana	PROPN
eurjchem-205	1	73	,	,	PUNCT
eurjchem-205	1	74	*	*	PUNCT
eurjchem-205	1	75	a	a	DET
eurjchem-205	1	76	division	division	NOUN
eurjchem-205	1	77	of	of	ADP
eurjchem-205	1	78	organic	organic	ADJ
eurjchem-205	1	79	chemistry	chemistry	NOUN
eurjchem-205	1	80	,	,	PUNCT
eurjchem-205	1	81	national	national	PROPN
eurjchem-205	1	82	chemical	chemical	PROPN
eurjchem-205	1	83	laboratory	laboratory	NOUN
eurjchem-205	1	84	,	,	PUNCT
eurjchem-205	1	85	pune	pune	NOUN
eurjchem-205	1	86	411008	411008	NUM
eurjchem-205	1	87	,	,	PUNCT
eurjchem-205	1	88	india	india	PROPN
eurjchem-205	1	89	b	b	PROPN
eurjchem-205	1	90	department	department	PROPN
eurjchem-205	1	91	of	of	ADP
eurjchem-205	1	92	pharmaceutical	pharmaceutical	ADJ
eurjchem-205	1	93	chemistry	chemistry	NOUN
eurjchem-205	1	94	,	,	PUNCT
eurjchem-205	1	95	sinhagad	sinhagad	ADP
eurjchem-205	1	96	college	college	PROPN
eurjchem-205	1	97	of	of	ADP
eurjchem-205	1	98	pharmacy	pharmacy	NOUN
eurjchem-205	1	99	,	,	PUNCT
eurjchem-205	1	100	pune	pune	NOUN
eurjchem-205	1	101	411041	411041	NUM
eurjchem-205	1	102	,	,	PUNCT
eurjchem-205	1	103	india	india	PROPN
eurjchem-205	1	104	c	c	PROPN
eurjchem-205	1	105	department	department	PROPN
eurjchem-205	1	106	of	of	ADP
eurjchem-205	1	107	pharmaceutical	pharmaceutical	ADJ
eurjchem-205	1	108	chemistry	chemistry	NOUN
eurjchem-205	1	109	,	,	PUNCT
eurjchem-205	1	110	all	all	DET
eurjchem-205	1	111	india	india	PROPN
eurjchem-205	1	112	shri	shri	PROPN
eurjchem-205	1	113	sivaji	sivaji	PROPN
eurjchem-205	1	114	memorial	memorial	PROPN
eurjchem-205	1	115	society	society	PROPN
eurjchem-205	1	116	’s	’s	PART
eurjchem-205	1	117	college	college	PROPN
eurjchem-205	1	118	of	of	ADP
eurjchem-205	1	119	pharmacy	pharmacy	NOUN
eurjchem-205	1	120	,	,	PUNCT
eurjchem-205	1	121	pune	pune	NOUN
eurjchem-205	1	122	411001	411001	NUM
eurjchem-205	1	123	,	,	PUNCT
eurjchem-205	1	124	india	india	PROPN
eurjchem-205	1	125	*	*	PUNCT
eurjchem-205	1	126	corresponding	correspond	VERB
eurjchem-205	1	127	author	author	NOUN
eurjchem-205	1	128	at	at	ADP
eurjchem-205	1	129	:	:	PUNCT
eurjchem-205	1	130	department	department	NOUN
eurjchem-205	1	131	of	of	ADP
eurjchem-205	1	132	pharmaceutical	pharmaceutical	ADJ
eurjchem-205	1	133	chemistry	chemistry	NOUN
eurjchem-205	1	134	,	,	PUNCT
eurjchem-205	1	135	sinhagad	sinhagad	ADP
eurjchem-205	1	136	college	college	PROPN
eurjchem-205	1	137	of	of	ADP
eurjchem-205	1	138	pharmacy	pharmacy	NOUN
eurjchem-205	1	139	,	,	PUNCT
eurjchem-205	1	140	pune	pune	NOUN
eurjchem-205	1	141	411041	411041	NUM
eurjchem-205	1	142	,	,	PUNCT
eurjchem-205	1	143	india	india	PROPN
eurjchem-205	1	144	.	.	PUNCT
eurjchem-205	2	1	tel	tel	PROPN
eurjchem-205	2	2	.	.	PUNCT
eurjchem-205	2	3	:	:	PUNCT
eurjchem-205	3	1	+91.9823318406	+91.9823318406	NUM
eurjchem-205	3	2	;	;	PUNCT
eurjchem-205	3	3	fax	fax	NOUN
eurjchem-205	3	4	:	:	PUNCT
eurjchem-205	3	5	+91.20.25902629	+91.20.25902629	NUM
eurjchem-205	3	6	.	.	PUNCT
eurjchem-205	3	7	e‐mail	e‐mail	PUNCT
eurjchem-205	3	8	address	address	NOUN
eurjchem-205	3	9	:	:	PUNCT
eurjchem-205	3	10	kumarv.srinivasan@gmail.com	kumarv.srinivasan@gmail.com	X
eurjchem-205	3	11	(	(	PUNCT
eurjchem-205	3	12	k.v	k.v	PROPN
eurjchem-205	3	13	.	.	PROPN
eurjchem-205	3	14	srinivasan	srinivasan	NOUN
eurjchem-205	3	15	)	)	PUNCT
eurjchem-205	3	16	.	.	PUNCT
eurjchem-205	4	1	article	article	NOUN
eurjchem-205	4	2	information	information	PROPN
eurjchem-205	4	3	abstract	abstract	ADV
eurjchem-205	4	4	received	receive	VERB
eurjchem-205	4	5	:	:	PUNCT
eurjchem-205	4	6	12	12	NUM
eurjchem-205	4	7	july	july	PROPN
eurjchem-205	4	8	2010	2010	NUM
eurjchem-205	4	9	received	receive	VERB
eurjchem-205	4	10	in	in	ADP
eurjchem-205	4	11	revised	revise	VERB
eurjchem-205	4	12	form	form	NOUN
eurjchem-205	4	13	:	:	PUNCT
eurjchem-205	4	14	24	24	NUM
eurjchem-205	4	15	november	november	PROPN
eurjchem-205	4	16	2010	2010	NUM
eurjchem-205	4	17	accepted	accept	VERB
eurjchem-205	4	18	:	:	PUNCT
eurjchem-205	4	19	15	15	NUM
eurjchem-205	4	20	december	december	PROPN
eurjchem-205	4	21	2010	2010	NUM
eurjchem-205	4	22	online	online	NOUN
eurjchem-205	4	23	:	:	PUNCT
eurjchem-205	4	24	30	30	NUM
eurjchem-205	4	25	june	june	PROPN
eurjchem-205	4	26	2011	2011	NUM
eurjchem-205	4	27	keywords	keyword	NOUN
eurjchem-205	4	28	luotonin	luotonin	ADJ
eurjchem-205	4	29	a	a	PRON
eurjchem-205	4	30	is	be	AUX
eurjchem-205	4	31	among	among	ADP
eurjchem-205	4	32	the	the	DET
eurjchem-205	4	33	first	first	ADJ
eurjchem-205	4	34	known	know	VERB
eurjchem-205	4	35	natural	natural	ADJ
eurjchem-205	4	36	product	product	NOUN
eurjchem-205	4	37	possessing	possess	VERB
eurjchem-205	4	38	the	the	DET
eurjchem-205	4	39	heteroaromatic	heteroaromatic	ADJ
eurjchem-205	4	40	pyrroloquinazoline	pyrroloquinazoline	NOUN
eurjchem-205	4	41	ring	ring	NOUN
eurjchem-205	4	42	system	system	NOUN
eurjchem-205	4	43	.	.	PUNCT
eurjchem-205	5	1	although	although	SCONJ
eurjchem-205	5	2	many	many	ADJ
eurjchem-205	5	3	syntheses	synthesis	NOUN
eurjchem-205	5	4	have	have	AUX
eurjchem-205	5	5	been	be	AUX
eurjchem-205	5	6	reported	report	VERB
eurjchem-205	5	7	for	for	ADP
eurjchem-205	5	8	this	this	DET
eurjchem-205	5	9	compound	compound	NOUN
eurjchem-205	5	10	,	,	PUNCT
eurjchem-205	5	11	but	but	CCONJ
eurjchem-205	5	12	they	they	PRON
eurjchem-205	5	13	all	all	PRON
eurjchem-205	5	14	have	have	VERB
eurjchem-205	5	15	one	one	NUM
eurjchem-205	5	16	or	or	CCONJ
eurjchem-205	5	17	the	the	DET
eurjchem-205	5	18	other	other	ADJ
eurjchem-205	5	19	draw	draw	VERB
eurjchem-205	5	20	back	back	ADV
eurjchem-205	5	21	such	such	ADJ
eurjchem-205	5	22	as	as	ADP
eurjchem-205	5	23	a	a	DET
eurjchem-205	5	24	large	large	ADJ
eurjchem-205	5	25	number	number	NOUN
eurjchem-205	5	26	of	of	ADP
eurjchem-205	5	27	steps	step	NOUN
eurjchem-205	5	28	,	,	PUNCT
eurjchem-205	5	29	use	use	NOUN
eurjchem-205	5	30	of	of	ADP
eurjchem-205	5	31	hazardous	hazardous	ADJ
eurjchem-205	5	32	reagents	reagent	NOUN
eurjchem-205	5	33	like	like	ADP
eurjchem-205	5	34	sodium	sodium	NOUN
eurjchem-205	5	35	hydride	hydride	NOUN
eurjchem-205	5	36	,	,	PUNCT
eurjchem-205	5	37	low	low	ADJ
eurjchem-205	5	38	temperature	temperature	NOUN
eurjchem-205	5	39	reactions	reaction	NOUN
eurjchem-205	5	40	,	,	PUNCT
eurjchem-205	5	41	and	and	CCONJ
eurjchem-205	5	42	lengthy	lengthy	ADJ
eurjchem-205	5	43	reaction	reaction	NOUN
eurjchem-205	5	44	time	time	NOUN
eurjchem-205	5	45	.	.	PUNCT
eurjchem-205	6	1	herein	herein	NOUN
eurjchem-205	6	2	we	we	PRON
eurjchem-205	6	3	report	report	VERB
eurjchem-205	6	4	the	the	DET
eurjchem-205	6	5	synthesis	synthesis	NOUN
eurjchem-205	6	6	of	of	ADP
eurjchem-205	6	7	luotonin	luotonin	PROPN
eurjchem-205	7	1	a	a	PRON
eurjchem-205	7	2	achieved	achieve	VERB
eurjchem-205	7	3	in	in	ADP
eurjchem-205	7	4	five	five	NUM
eurjchem-205	7	5	steps	step	NOUN
eurjchem-205	7	6	in	in	ADP
eurjchem-205	7	7	which	which	PRON
eurjchem-205	7	8	,	,	PUNCT
eurjchem-205	7	9	two	two	NUM
eurjchem-205	7	10	of	of	ADP
eurjchem-205	7	11	the	the	DET
eurjchem-205	7	12	steps	step	NOUN
eurjchem-205	7	13	involved	involve	VERB
eurjchem-205	7	14	green	green	ADJ
eurjchem-205	7	15	solvents	solvent	NOUN
eurjchem-205	7	16	such	such	ADJ
eurjchem-205	7	17	as	as	ADP
eurjchem-205	7	18	an	an	DET
eurjchem-205	7	19	ionic	ionic	ADJ
eurjchem-205	7	20	liquid	liquid	NOUN
eurjchem-205	7	21	and	and	CCONJ
eurjchem-205	7	22	water	water	NOUN
eurjchem-205	7	23	as	as	ADP
eurjchem-205	7	24	reaction	reaction	NOUN
eurjchem-205	7	25	media	medium	NOUN
eurjchem-205	7	26	.	.	PUNCT
eurjchem-205	8	1	in	in	ADP
eurjchem-205	8	2	particular	particular	ADJ
eurjchem-205	8	3	,	,	PUNCT
eurjchem-205	8	4	we	we	PRON
eurjchem-205	8	5	have	have	AUX
eurjchem-205	8	6	achieved	achieve	VERB
eurjchem-205	8	7	the	the	DET
eurjchem-205	8	8	reaction	reaction	NOUN
eurjchem-205	8	9	steps	step	NOUN
eurjchem-205	8	10	1	1	NUM
eurjchem-205	8	11	and	and	CCONJ
eurjchem-205	8	12	3	3	NUM
eurjchem-205	8	13	involving	involve	VERB
eurjchem-205	8	14	the	the	DET
eurjchem-205	8	15	green	green	ADJ
eurjchem-205	8	16	solvents	solvent	NOUN
eurjchem-205	8	17	in	in	ADP
eurjchem-205	8	18	much	much	ADV
eurjchem-205	8	19	shorter	short	ADJ
eurjchem-205	8	20	reaction	reaction	NOUN
eurjchem-205	8	21	time	time	NOUN
eurjchem-205	8	22	than	than	SCONJ
eurjchem-205	8	23	hitherto	hitherto	NOUN
eurjchem-205	8	24	reported	report	VERB
eurjchem-205	8	25	.	.	PUNCT
eurjchem-205	9	1	ionic	ionic	ADJ
eurjchem-205	9	2	liquids	liquid	NOUN
eurjchem-205	9	3	luotonin	luotonin	ADP
eurjchem-205	9	4	a	a	DET
eurjchem-205	9	5	water	water	NOUN
eurjchem-205	9	6	pyrroloquinazoline	pyrroloquinazoline	NOUN
eurjchem-205	9	7	volatile	volatile	ADJ
eurjchem-205	9	8	organic	organic	ADJ
eurjchem-205	9	9	compounds	compound	NOUN
eurjchem-205	9	10	anticancer	anticancer	NOUN
eurjchem-205	9	11	activity	activity	NOUN
eurjchem-205	9	12	1	1	NUM
eurjchem-205	9	13	.	.	PUNCT
eurjchem-205	10	1	introduction	introduction	NOUN
eurjchem-205	10	2	heterocyclic	heterocyclic	ADJ
eurjchem-205	10	3	compounds	compound	NOUN
eurjchem-205	10	4	are	be	AUX
eurjchem-205	10	5	of	of	ADP
eurjchem-205	10	6	particular	particular	ADJ
eurjchem-205	10	7	interest	interest	NOUN
eurjchem-205	10	8	in	in	ADP
eurjchem-205	10	9	medicinal	medicinal	ADJ
eurjchem-205	10	10	chemistry	chemistry	NOUN
eurjchem-205	10	11	.	.	PUNCT
eurjchem-205	11	1	among	among	ADP
eurjchem-205	11	2	these	these	PRON
eurjchem-205	11	3	,	,	PUNCT
eurjchem-205	11	4	alkaloids	alkaloid	NOUN
eurjchem-205	11	5	that	that	PRON
eurjchem-205	11	6	incorporate	incorporate	VERB
eurjchem-205	11	7	the	the	DET
eurjchem-205	11	8	pyrroloquinazoline	pyrroloquinazoline	NOUN
eurjchem-205	11	9	chromophores	chromophore	NOUN
eurjchem-205	11	10	have	have	AUX
eurjchem-205	11	11	been	be	AUX
eurjchem-205	11	12	isolated	isolate	VERB
eurjchem-205	11	13	form	form	NOUN
eurjchem-205	11	14	natural	natural	ADJ
eurjchem-205	11	15	sources	source	NOUN
eurjchem-205	11	16	[	[	X
eurjchem-205	11	17	1,2	1,2	NUM
eurjchem-205	11	18	]	]	PUNCT
eurjchem-205	11	19	display	display	NOUN
eurjchem-205	11	20	a	a	DET
eurjchem-205	11	21	wide	wide	ADJ
eurjchem-205	11	22	range	range	NOUN
eurjchem-205	11	23	of	of	ADP
eurjchem-205	11	24	biological	biological	ADJ
eurjchem-205	11	25	activities	activity	NOUN
eurjchem-205	11	26	[	[	X
eurjchem-205	11	27	3‐5	3‐5	NUM
eurjchem-205	11	28	]	]	PUNCT
eurjchem-205	11	29	.	.	PUNCT
eurjchem-205	12	1	luotonin	luotonin	INTJ
eurjchem-205	12	2	a	a	DET
eurjchem-205	12	3	(	(	PUNCT
eurjchem-205	12	4	figure	figure	NOUN
eurjchem-205	12	5	1	1	NUM
eurjchem-205	12	6	)	)	PUNCT
eurjchem-205	12	7	,	,	PUNCT
eurjchem-205	12	8	the	the	DET
eurjchem-205	12	9	first	first	ADJ
eurjchem-205	12	10	known	know	VERB
eurjchem-205	12	11	natural	natural	ADJ
eurjchem-205	12	12	product	product	NOUN
eurjchem-205	12	13	to	to	PART
eurjchem-205	12	14	possess	possess	VERB
eurjchem-205	12	15	the	the	DET
eurjchem-205	12	16	heteroaromatic	heteroaromatic	ADJ
eurjchem-205	12	17	pyrroloquinazoline	pyrroloquinazoline	NOUN
eurjchem-205	12	18	ring	ring	NOUN
eurjchem-205	12	19	system	system	NOUN
eurjchem-205	12	20	,	,	PUNCT
eurjchem-205	12	21	has	have	AUX
eurjchem-205	12	22	been	be	AUX
eurjchem-205	12	23	isolated	isolate	VERB
eurjchem-205	12	24	by	by	ADP
eurjchem-205	12	25	nomura	nomura	NOUN
eurjchem-205	12	26	and	and	CCONJ
eurjchem-205	12	27	co‐workers	co‐worker	NOUN
eurjchem-205	12	28	in	in	ADP
eurjchem-205	12	29	1997	1997	NUM
eurjchem-205	12	30	from	from	ADP
eurjchem-205	12	31	the	the	DET
eurjchem-205	12	32	aerial	aerial	ADJ
eurjchem-205	12	33	parts	part	NOUN
eurjchem-205	12	34	of	of	ADP
eurjchem-205	12	35	the	the	DET
eurjchem-205	12	36	peganum	peganum	ADJ
eurjchem-205	12	37	nigellastrum	nigellastrum	NOUN
eurjchem-205	12	38	(	(	PUNCT
eurjchem-205	12	39	chinese	chinese	ADJ
eurjchem-205	12	40	bung	bung	NOUN
eurjchem-205	12	41	)	)	PUNCT
eurjchem-205	13	1	[	[	X
eurjchem-205	13	2	6	6	NUM
eurjchem-205	13	3	]	]	PUNCT
eurjchem-205	13	4	.	.	PUNCT
eurjchem-205	14	1	luotonin	luotonin	PROPN
eurjchem-205	15	1	a	a	DET
eurjchem-205	15	2	showed	show	VERB
eurjchem-205	15	3	potent	potent	ADJ
eurjchem-205	15	4	cytotoxic	cytotoxic	ADJ
eurjchem-205	15	5	activity	activity	NOUN
eurjchem-205	15	6	against	against	ADP
eurjchem-205	15	7	mouse	mouse	NOUN
eurjchem-205	15	8	leukemia	leukemia	NOUN
eurjchem-205	15	9	p‐388	p‐388	PRON
eurjchem-205	15	10	cells	cell	NOUN
eurjchem-205	15	11	and	and	CCONJ
eurjchem-205	15	12	has	have	AUX
eurjchem-205	15	13	been	be	AUX
eurjchem-205	15	14	the	the	DET
eurjchem-205	15	15	subject	subject	NOUN
eurjchem-205	15	16	of	of	ADP
eurjchem-205	15	17	several	several	ADJ
eurjchem-205	15	18	syntheses	synthesis	NOUN
eurjchem-205	15	19	[	[	X
eurjchem-205	15	20	6	6	NUM
eurjchem-205	15	21	]	]	PUNCT
eurjchem-205	15	22	.	.	PUNCT
eurjchem-205	16	1	there	there	PRON
eurjchem-205	16	2	are	be	VERB
eurjchem-205	16	3	obvious	obvious	ADJ
eurjchem-205	16	4	similarities	similarity	NOUN
eurjchem-205	16	5	between	between	ADP
eurjchem-205	16	6	a	a	DET
eurjchem-205	16	7	good	good	ADJ
eurjchem-205	16	8	lead	lead	NOUN
eurjchem-205	16	9	anticancer	anticancer	NOUN
eurjchem-205	16	10	agent	agent	NOUN
eurjchem-205	16	11	,	,	PUNCT
eurjchem-205	16	12	20‐(s)‐campothecin	20‐(s)‐campothecin	NUM
eurjchem-205	16	13	[	[	X
eurjchem-205	16	14	7‐13	7‐13	X
eurjchem-205	16	15	]	]	PUNCT
eurjchem-205	16	16	and	and	CCONJ
eurjchem-205	16	17	luotonin	luotonin	ADV
eurjchem-205	16	18	a	a	DET
eurjchem-205	16	19	notably	notably	ADV
eurjchem-205	16	20	in	in	ADP
eurjchem-205	16	21	identical	identical	ADJ
eurjchem-205	16	22	rings	ring	NOUN
eurjchem-205	16	23	abc	abc	PROPN
eurjchem-205	17	1	[	[	X
eurjchem-205	17	2	14,15	14,15	NUM
eurjchem-205	17	3	]	]	PUNCT
eurjchem-205	17	4	.	.	PUNCT
eurjchem-205	18	1	figure	figure	NOUN
eurjchem-205	18	2	1	1	NUM
eurjchem-205	18	3	.	.	PUNCT
eurjchem-205	18	4	structures	structure	NOUN
eurjchem-205	18	5	of	of	ADP
eurjchem-205	18	6	luotonin	luotonin	ADJ
eurjchem-205	18	7	a	a	PRON
eurjchem-205	18	8	and	and	CCONJ
eurjchem-205	18	9	20‐(s)‐campothecin	20‐(s)‐campothecin	NUM
eurjchem-205	18	10	.	.	PUNCT
eurjchem-205	19	1	interest	interest	NOUN
eurjchem-205	19	2	in	in	ADP
eurjchem-205	19	3	luotonin	luotonin	PROPN
eurjchem-205	19	4	a	a	PRON
eurjchem-205	19	5	has	have	AUX
eurjchem-205	19	6	increased	increase	VERB
eurjchem-205	19	7	considerably	considerably	ADV
eurjchem-205	19	8	following	follow	VERB
eurjchem-205	19	9	the	the	DET
eurjchem-205	19	10	report	report	NOUN
eurjchem-205	19	11	by	by	ADP
eurjchem-205	19	12	hecht	hecht	PROPN
eurjchem-205	19	13	and	and	CCONJ
eurjchem-205	19	14	coworkers	coworker	NOUN
eurjchem-205	19	15	that	that	SCONJ
eurjchem-205	19	16	it	it	PRON
eurjchem-205	19	17	mediates	mediate	VERB
eurjchem-205	19	18	topoisomerase‐dependent	topoisomerase‐dependent	NOUN
eurjchem-205	19	19	cytotoxicity	cytotoxicity	NOUN
eurjchem-205	19	20	[	[	X
eurjchem-205	19	21	16	16	NUM
eurjchem-205	19	22	]	]	PUNCT
eurjchem-205	19	23	.	.	PUNCT
eurjchem-205	20	1	these	these	PRON
eurjchem-205	20	2	observa‐	observa‐	PROPN
eurjchem-205	20	3	tions	tion	NOUN
eurjchem-205	20	4	are	be	AUX
eurjchem-205	20	5	important	important	ADJ
eurjchem-205	20	6	because	because	SCONJ
eurjchem-205	20	7	it	it	PRON
eurjchem-205	20	8	has	have	AUX
eurjchem-205	20	9	been	be	AUX
eurjchem-205	20	10	thought	think	VERB
eurjchem-205	20	11	until	until	ADP
eurjchem-205	20	12	very	very	ADV
eurjchem-205	20	13	recently	recently	ADV
eurjchem-205	20	14	that	that	SCONJ
eurjchem-205	20	15	the	the	DET
eurjchem-205	20	16	e‐ring	e‐re	VERB
eurjchem-205	20	17	hydroxylactone	hydroxylactone	NOUN
eurjchem-205	20	18	of	of	ADP
eurjchem-205	20	19	campothecin	campothecin	NOUN
eurjchem-205	20	20	was	be	AUX
eurjchem-205	20	21	indispensable	indispensable	ADJ
eurjchem-205	20	22	for	for	ADP
eurjchem-205	20	23	anticancer	anticancer	NOUN
eurjchem-205	20	24	activity	activity	NOUN
eurjchem-205	20	25	[	[	X
eurjchem-205	20	26	17‐19	17‐19	NUM
eurjchem-205	20	27	]	]	PUNCT
eurjchem-205	20	28	.	.	PUNCT
eurjchem-205	21	1	however	however	ADV
eurjchem-205	21	2	luotonin	luotonin	ADV
eurjchem-205	21	3	is	be	AUX
eurjchem-205	21	4	a	a	DET
eurjchem-205	21	5	good	good	ADJ
eurjchem-205	21	6	lead	lead	NOUN
eurjchem-205	21	7	compound	compound	NOUN
eurjchem-205	21	8	and	and	CCONJ
eurjchem-205	21	9	hecht	hecht	PROPN
eurjchem-205	22	1	[	[	X
eurjchem-205	22	2	20,21	20,21	NUM
eurjchem-205	22	3	]	]	PUNCT
eurjchem-205	22	4	,	,	PUNCT
eurjchem-205	22	5	dallavalle	dallavalle	X
eurjchem-205	22	6	[	[	X
eurjchem-205	22	7	22	22	NUM
eurjchem-205	22	8	]	]	PUNCT
eurjchem-205	22	9	and	and	CCONJ
eurjchem-205	22	10	their	their	PRON
eurjchem-205	22	11	coworkers	coworker	NOUN
eurjchem-205	22	12	recently	recently	ADV
eurjchem-205	22	13	reported	report	VERB
eurjchem-205	22	14	the	the	DET
eurjchem-205	22	15	synthesis	synthesis	NOUN
eurjchem-205	22	16	of	of	ADP
eurjchem-205	22	17	an	an	DET
eurjchem-205	22	18	assortment	assortment	NOUN
eurjchem-205	22	19	of	of	ADP
eurjchem-205	22	20	substituted	substitute	VERB
eurjchem-205	22	21	e‐ring	e‐re	VERB
eurjchem-205	22	22	analogues	analogue	NOUN
eurjchem-205	22	23	with	with	ADP
eurjchem-205	22	24	a	a	DET
eurjchem-205	22	25	few	few	ADJ
eurjchem-205	22	26	a	a	DET
eurjchem-205	22	27	ring	ring	NOUN
eurjchem-205	22	28	analogues	analogue	NOUN
eurjchem-205	22	29	.	.	PUNCT
eurjchem-205	23	1	in	in	ADP
eurjchem-205	23	2	view	view	NOUN
eurjchem-205	23	3	of	of	ADP
eurjchem-205	23	4	the	the	DET
eurjchem-205	23	5	importance	importance	NOUN
eurjchem-205	23	6	of	of	ADP
eurjchem-205	23	7	luotonin	luotonin	ADJ
eurjchem-205	23	8	a	a	PRON
eurjchem-205	23	9	and	and	CCONJ
eurjchem-205	23	10	its	its	PRON
eurjchem-205	23	11	derivatives	derivative	NOUN
eurjchem-205	23	12	in	in	ADP
eurjchem-205	23	13	medicinal	medicinal	ADJ
eurjchem-205	23	14	chemistry	chemistry	NOUN
eurjchem-205	23	15	,	,	PUNCT
eurjchem-205	23	16	a	a	DET
eurjchem-205	23	17	number	number	NOUN
eurjchem-205	23	18	of	of	ADP
eurjchem-205	23	19	total	total	ADJ
eurjchem-205	23	20	syntheses	synthesis	NOUN
eurjchem-205	23	21	have	have	AUX
eurjchem-205	23	22	been	be	AUX
eurjchem-205	23	23	reported	report	VERB
eurjchem-205	23	24	in	in	ADP
eurjchem-205	23	25	literature	literature	NOUN
eurjchem-205	23	26	[	[	X
eurjchem-205	23	27	23‐38	23‐38	X
eurjchem-205	23	28	]	]	X
eurjchem-205	23	29	.	.	PUNCT
eurjchem-205	24	1	although	although	SCONJ
eurjchem-205	24	2	many	many	ADJ
eurjchem-205	24	3	syntheses	synthesis	NOUN
eurjchem-205	24	4	have	have	AUX
eurjchem-205	24	5	been	be	AUX
eurjchem-205	24	6	reported	report	VERB
eurjchem-205	24	7	,	,	PUNCT
eurjchem-205	24	8	they	they	PRON
eurjchem-205	24	9	all	all	PRON
eurjchem-205	24	10	have	have	VERB
eurjchem-205	24	11	the	the	DET
eurjchem-205	24	12	one	one	NUM
eurjchem-205	24	13	or	or	CCONJ
eurjchem-205	24	14	the	the	DET
eurjchem-205	24	15	other	other	ADJ
eurjchem-205	24	16	draw	draw	VERB
eurjchem-205	24	17	back	back	ADV
eurjchem-205	24	18	of	of	ADP
eurjchem-205	24	19	large	large	ADJ
eurjchem-205	24	20	number	number	NOUN
eurjchem-205	24	21	of	of	ADP
eurjchem-205	24	22	steps	step	NOUN
eurjchem-205	24	23	,	,	PUNCT
eurjchem-205	24	24	use	use	NOUN
eurjchem-205	24	25	of	of	ADP
eurjchem-205	24	26	hazardous	hazardous	ADJ
eurjchem-205	24	27	reagents	reagent	NOUN
eurjchem-205	24	28	like	like	ADP
eurjchem-205	24	29	sodium	sodium	NOUN
eurjchem-205	24	30	hydride	hydride	NOUN
eurjchem-205	24	31	,	,	PUNCT
eurjchem-205	24	32	low	low	ADJ
eurjchem-205	24	33	temperature	temperature	NOUN
eurjchem-205	24	34	reactions	reaction	NOUN
eurjchem-205	24	35	and	and	CCONJ
eurjchem-205	24	36	lengthy	lengthy	ADJ
eurjchem-205	24	37	reaction	reaction	NOUN
eurjchem-205	24	38	time	time	NOUN
eurjchem-205	24	39	.	.	PUNCT
eurjchem-205	25	1	in	in	ADP
eurjchem-205	25	2	many	many	ADJ
eurjchem-205	25	3	synthesis	synthesis	NOUN
eurjchem-205	25	4	,	,	PUNCT
eurjchem-205	25	5	the	the	DET
eurjchem-205	25	6	use	use	NOUN
eurjchem-205	25	7	of	of	ADP
eurjchem-205	25	8	halogenated	halogenated	ADJ
eurjchem-205	25	9	volatile	volatile	ADJ
eurjchem-205	25	10	organic	organic	ADJ
eurjchem-205	25	11	compounds	compound	NOUN
eurjchem-205	25	12	(	(	PUNCT
eurjchem-205	25	13	voc	voc	NOUN
eurjchem-205	25	14	)	)	PUNCT
eurjchem-205	25	15	like	like	ADP
eurjchem-205	25	16	dichloromethane	dichloromethane	NOUN
eurjchem-205	25	17	or	or	CCONJ
eurjchem-205	25	18	solvents	solvent	NOUN
eurjchem-205	25	19	like	like	ADP
eurjchem-205	25	20	benzene	benzene	NOUN
eurjchem-205	25	21	and	and	CCONJ
eurjchem-205	25	22	dimethylformamide	dimethylformamide	NOUN
eurjchem-205	25	23	are	be	AUX
eurjchem-205	25	24	detrimental	detrimental	ADJ
eurjchem-205	25	25	to	to	ADP
eurjchem-205	25	26	the	the	DET
eurjchem-205	25	27	environment	environment	NOUN
eurjchem-205	25	28	which	which	PRON
eurjchem-205	25	29	need	need	VERB
eurjchem-205	25	30	to	to	PART
eurjchem-205	25	31	be	be	AUX
eurjchem-205	25	32	recovered	recover	VERB
eurjchem-205	25	33	and	and	CCONJ
eurjchem-205	25	34	recycled	recycle	VERB
eurjchem-205	25	35	completely	completely	ADV
eurjchem-205	25	36	adding	add	VERB
eurjchem-205	25	37	to	to	ADP
eurjchem-205	25	38	the	the	DET
eurjchem-205	25	39	economics	economic	NOUN
eurjchem-205	25	40	of	of	ADP
eurjchem-205	25	41	the	the	DET
eurjchem-205	25	42	process	process	NOUN
eurjchem-205	25	43	.	.	PUNCT
eurjchem-205	26	1	in	in	ADP
eurjchem-205	26	2	continuation	continuation	NOUN
eurjchem-205	26	3	of	of	ADP
eurjchem-205	26	4	our	our	PRON
eurjchem-205	26	5	ongoing	ongoing	ADJ
eurjchem-205	26	6	work	work	NOUN
eurjchem-205	26	7	on	on	ADP
eurjchem-205	26	8	the	the	DET
eurjchem-205	26	9	synthesis	synthesis	NOUN
eurjchem-205	26	10	of	of	ADP
eurjchem-205	26	11	bioactive	bioactive	ADJ
eurjchem-205	26	12	natural	natural	ADJ
eurjchem-205	26	13	products	product	NOUN
eurjchem-205	26	14	,	,	PUNCT
eurjchem-205	26	15	we	we	PRON
eurjchem-205	26	16	herein	herein	VERB
eurjchem-205	26	17	report	report	VERB
eurjchem-205	26	18	the	the	DET
eurjchem-205	26	19	formal	formal	ADJ
eurjchem-205	26	20	synthesis	synthesis	NOUN
eurjchem-205	26	21	of	of	ADP
eurjchem-205	26	22	luotonin	luotonin	ADV
eurjchem-205	26	23	a	a	PRON
eurjchem-205	26	24	which	which	PRON
eurjchem-205	26	25	avoids	avoid	VERB
eurjchem-205	26	26	many	many	ADJ
eurjchem-205	26	27	of	of	ADP
eurjchem-205	26	28	the	the	DET
eurjchem-205	26	29	above	above	ADJ
eurjchem-205	26	30	mentioned	mention	VERB
eurjchem-205	26	31	drawbacks	drawback	NOUN
eurjchem-205	26	32	.	.	PUNCT
eurjchem-205	27	1	we	we	PRON
eurjchem-205	27	2	initiated	initiate	VERB
eurjchem-205	27	3	this	this	DET
eurjchem-205	27	4	study	study	NOUN
eurjchem-205	27	5	with	with	ADP
eurjchem-205	27	6	the	the	DET
eurjchem-205	27	7	goal	goal	NOUN
eurjchem-205	27	8	of	of	ADP
eurjchem-205	27	9	expanding	expand	VERB
eurjchem-205	27	10	the	the	DET
eurjchem-205	27	11	efficacy	efficacy	NOUN
eurjchem-205	27	12	and	and	CCONJ
eurjchem-205	27	13	efficiency	efficiency	NOUN
eurjchem-205	27	14	of	of	ADP
eurjchem-205	27	15	the	the	DET
eurjchem-205	27	16	methodologies	methodology	NOUN
eurjchem-205	27	17	developed	develop	VERB
eurjchem-205	27	18	by	by	ADP
eurjchem-205	27	19	us	we	PRON
eurjchem-205	27	20	using	use	VERB
eurjchem-205	27	21	ionic	ionic	ADJ
eurjchem-205	27	22	liquids	liquid	NOUN
eurjchem-205	27	23	[	[	X
eurjchem-205	27	24	39	39	NUM
eurjchem-205	27	25	]	]	PUNCT
eurjchem-205	27	26	for	for	ADP
eurjchem-205	27	27	the	the	DET
eurjchem-205	27	28	synthesis	synthesis	NOUN
eurjchem-205	27	29	of	of	ADP
eurjchem-205	27	30	luotonin	luotonin	ADJ
eurjchem-205	27	31	a	a	PRON
eurjchem-205	27	32	,	,	PUNCT
eurjchem-205	27	33	particularly	particularly	ADV
eurjchem-205	27	34	for	for	ADP
eurjchem-205	27	35	the	the	DET
eurjchem-205	27	36	first	first	ADJ
eurjchem-205	27	37	step	step	NOUN
eurjchem-205	27	38	and	and	CCONJ
eurjchem-205	27	39	the	the	DET
eurjchem-205	27	40	involvement	involvement	NOUN
eurjchem-205	27	41	of	of	ADP
eurjchem-205	27	42	water	water	NOUN
eurjchem-205	27	43	as	as	ADP
eurjchem-205	27	44	solvent	solvent	NOUN
eurjchem-205	27	45	in	in	ADP
eurjchem-205	27	46	another	another	DET
eurjchem-205	27	47	step	step	NOUN
eurjchem-205	27	48	.	.	PUNCT
eurjchem-205	28	1	2	2	X
eurjchem-205	28	2	.	.	X
eurjchem-205	28	3	experimental	experimental	ADJ
eurjchem-205	28	4	2.1	2.1	NUM
eurjchem-205	28	5	.	.	PUNCT
eurjchem-205	29	1	instrumentation	instrumentation	NOUN
eurjchem-205	29	2	melting	melting	NOUN
eurjchem-205	29	3	points	point	NOUN
eurjchem-205	29	4	were	be	AUX
eurjchem-205	29	5	recorded	record	VERB
eurjchem-205	29	6	in	in	ADP
eurjchem-205	29	7	open	open	ADJ
eurjchem-205	29	8	capillary	capillary	ADJ
eurjchem-205	29	9	on	on	ADP
eurjchem-205	29	10	buchi	buchi	PROPN
eurjchem-205	29	11	melting	melt	VERB
eurjchem-205	29	12	point	point	NOUN
eurjchem-205	29	13	b‐540	b‐540	VERB
eurjchem-205	29	14	apparatus	apparatus	NOUN
eurjchem-205	29	15	and	and	CCONJ
eurjchem-205	29	16	are	be	AUX
eurjchem-205	29	17	uncorrected	uncorrecte	VERB
eurjchem-205	29	18	.	.	PUNCT
eurjchem-205	30	1	1h	1h	NUM
eurjchem-205	30	2	nmr	nmr	NOUN
eurjchem-205	30	3	236	236	NUM
eurjchem-205	30	4	potewar	potewar	NOUN
eurjchem-205	30	5	et	et	PROPN
eurjchem-205	30	6	al	al	PROPN
eurjchem-205	30	7	.	.	PUNCT
eurjchem-205	30	8	/	/	SYM
eurjchem-205	30	9	european	european	PROPN
eurjchem-205	30	10	journal	journal	PROPN
eurjchem-205	30	11	of	of	ADP
eurjchem-205	30	12	chemistry	chemistry	NOUN
eurjchem-205	30	13	2	2	NUM
eurjchem-205	30	14	(	(	PUNCT
eurjchem-205	30	15	2	2	NUM
eurjchem-205	30	16	)	)	PUNCT
eurjchem-205	30	17	(	(	PUNCT
eurjchem-205	30	18	2011	2011	NUM
eurjchem-205	30	19	)	)	PUNCT
eurjchem-205	30	20	235‐237	235‐237	NUM
eurjchem-205	30	21	spectra	spectra	NOUN
eurjchem-205	30	22	were	be	AUX
eurjchem-205	30	23	recorded	record	VERB
eurjchem-205	30	24	on	on	ADP
eurjchem-205	30	25	bruker	bruker	NOUN
eurjchem-205	30	26	ac‐200	ac‐200	NOUN
eurjchem-205	30	27	mhz	mhz	NOUN
eurjchem-205	30	28	,	,	PUNCT
eurjchem-205	30	29	msl‐300	msl‐300	ADJ
eurjchem-205	30	30	mhz	mhz	NOUN
eurjchem-205	30	31	and	and	CCONJ
eurjchem-205	30	32	drx‐500	drx‐500	VERB
eurjchem-205	30	33	mhz	mhz	ADJ
eurjchem-205	30	34	spectrometers	spectrometer	NOUN
eurjchem-205	30	35	using	use	VERB
eurjchem-205	30	36	tetramethylsilane	tetramethylsilane	PROPN
eurjchem-205	30	37	(	(	PUNCT
eurjchem-205	30	38	tms	tms	PROPN
eurjchem-205	30	39	)	)	PUNCT
eurjchem-205	30	40	as	as	ADP
eurjchem-205	30	41	an	an	DET
eurjchem-205	30	42	internal	internal	ADJ
eurjchem-205	30	43	standard	standard	NOUN
eurjchem-205	30	44	.	.	PUNCT
eurjchem-205	31	1	chemical	chemical	ADJ
eurjchem-205	31	2	shifts	shift	NOUN
eurjchem-205	31	3	have	have	AUX
eurjchem-205	31	4	been	be	AUX
eurjchem-205	31	5	expressed	express	VERB
eurjchem-205	31	6	in	in	ADP
eurjchem-205	31	7	ppm	ppm	ADJ
eurjchem-205	31	8	units	unit	NOUN
eurjchem-205	31	9	downfield	downfield	VERB
eurjchem-205	31	10	from	from	ADP
eurjchem-205	31	11	tms	tms	PROPN
eurjchem-205	31	12	.	.	PUNCT
eurjchem-205	32	1	13	13	NUM
eurjchem-205	32	2	c	c	PROPN
eurjchem-205	32	3	nmr	nmr	NOUN
eurjchem-205	32	4	spectra	spectra	NOUN
eurjchem-205	32	5	were	be	AUX
eurjchem-205	32	6	recorded	record	VERB
eurjchem-205	32	7	on	on	ADP
eurjchem-205	32	8	bruker	bruker	NOUN
eurjchem-205	32	9	ac‐50	ac‐50	ADP
eurjchem-205	32	10	mhz	mhz	ADJ
eurjchem-205	32	11	,	,	PUNCT
eurjchem-205	32	12	msl‐75	msl‐75	ADJ
eurjchem-205	32	13	mhz	mhz	NOUN
eurjchem-205	32	14	and	and	CCONJ
eurjchem-205	32	15	drx‐	drx‐	NOUN
eurjchem-205	32	16	125	125	NUM
eurjchem-205	32	17	mhz	mhz	NOUN
eurjchem-205	32	18	spectrometers	spectrometer	NOUN
eurjchem-205	32	19	.	.	PUNCT
eurjchem-205	33	1	elemental	elemental	ADJ
eurjchem-205	33	2	analyses	analysis	NOUN
eurjchem-205	33	3	were	be	AUX
eurjchem-205	33	4	obtained	obtain	VERB
eurjchem-205	33	5	using	use	VERB
eurjchem-205	33	6	a	a	DET
eurjchem-205	33	7	flash	flash	NOUN
eurjchem-205	33	8	ea	ea	ADP
eurjchem-205	33	9	1112	1112	NUM
eurjchem-205	33	10	thermofinnigan	thermofinnigan	NOUN
eurjchem-205	33	11	instrument	instrument	NOUN
eurjchem-205	33	12	.	.	PUNCT
eurjchem-205	34	1	2.2	2.2	NUM
eurjchem-205	34	2	.	.	PUNCT
eurjchem-205	34	3	synthesis	synthesis	NOUN
eurjchem-205	34	4	of	of	ADP
eurjchem-205	34	5	methyl	methyl	NOUN
eurjchem-205	34	6	2‐methyquinoline‐3‐carboxylate	2‐methyquinoline‐3‐carboxylate	NUM
eurjchem-205	34	7	(	(	PUNCT
eurjchem-205	34	8	3	3	NUM
eurjchem-205	34	9	)	)	PUNCT
eurjchem-205	34	10	a	a	DET
eurjchem-205	34	11	mixture	mixture	NOUN
eurjchem-205	34	12	of	of	ADP
eurjchem-205	34	13	2‐aminobenzaldehyde	2‐aminobenzaldehyde	NUM
eurjchem-205	34	14	1	1	NUM
eurjchem-205	34	15	(	(	PUNCT
eurjchem-205	34	16	1.0	1.0	NUM
eurjchem-205	34	17	g	g	NOUN
eurjchem-205	34	18	,	,	PUNCT
eurjchem-205	34	19	8.2	8.2	NUM
eurjchem-205	34	20	mmol	mmol	NOUN
eurjchem-205	34	21	)	)	PUNCT
eurjchem-205	34	22	and	and	CCONJ
eurjchem-205	34	23	methyl	methyl	NOUN
eurjchem-205	34	24	acetoacetate	acetoacetate	NOUN
eurjchem-205	34	25	2	2	NUM
eurjchem-205	34	26	(	(	PUNCT
eurjchem-205	34	27	1.1	1.1	NUM
eurjchem-205	34	28	g	g	NOUN
eurjchem-205	34	29	,	,	PUNCT
eurjchem-205	34	30	9.9	9.9	NUM
eurjchem-205	34	31	mmol	mmol	NOUN
eurjchem-205	34	32	)	)	PUNCT
eurjchem-205	34	33	in	in	ADP
eurjchem-205	34	34	the	the	DET
eurjchem-205	34	35	ionic	ionic	ADJ
eurjchem-205	34	36	liquid	liquid	NOUN
eurjchem-205	34	37	(	(	PUNCT
eurjchem-205	34	38	il	il	PROPN
eurjchem-205	34	39	)	)	PUNCT
eurjchem-205	34	40	,	,	PUNCT
eurjchem-205	34	41	1‐n‐butyl‐imidazolium	1‐n‐butyl‐imidazolium	NUM
eurjchem-205	34	42	tertrafluoroborate	tertrafluoroborate	NOUN
eurjchem-205	34	43	(	(	PUNCT
eurjchem-205	34	44	[	[	X
eurjchem-205	34	45	hbim]bf4	hbim]bf4	X
eurjchem-205	34	46	)	)	PUNCT
eurjchem-205	34	47	(	(	PUNCT
eurjchem-205	34	48	10	10	NUM
eurjchem-205	34	49	ml	ml	NOUN
eurjchem-205	34	50	)	)	PUNCT
eurjchem-205	34	51	was	be	AUX
eurjchem-205	34	52	heated	heat	VERB
eurjchem-205	34	53	at	at	ADP
eurjchem-205	34	54	100	100	NUM
eurjchem-205	34	55	oc	oc	NOUN
eurjchem-205	34	56	with	with	ADP
eurjchem-205	34	57	stirring	stir	VERB
eurjchem-205	34	58	for	for	ADP
eurjchem-205	34	59	1.5	1.5	NUM
eurjchem-205	34	60	h.	h.	NOUN
eurjchem-205	34	61	the	the	DET
eurjchem-205	34	62	progress	progress	NOUN
eurjchem-205	34	63	of	of	ADP
eurjchem-205	34	64	reaction	reaction	NOUN
eurjchem-205	34	65	was	be	AUX
eurjchem-205	34	66	monitored	monitor	VERB
eurjchem-205	34	67	by	by	ADP
eurjchem-205	34	68	thin	thin	ADJ
eurjchem-205	34	69	layer	layer	NOUN
eurjchem-205	34	70	chromatography	chromatography	NOUN
eurjchem-205	34	71	(	(	PUNCT
eurjchem-205	34	72	tlc	tlc	NOUN
eurjchem-205	34	73	)	)	PUNCT
eurjchem-205	34	74	.	.	PUNCT
eurjchem-205	35	1	after	after	ADP
eurjchem-205	35	2	completion	completion	NOUN
eurjchem-205	35	3	of	of	ADP
eurjchem-205	35	4	reaction	reaction	NOUN
eurjchem-205	35	5	,	,	PUNCT
eurjchem-205	35	6	the	the	DET
eurjchem-205	35	7	reaction	reaction	NOUN
eurjchem-205	35	8	mixture	mixture	NOUN
eurjchem-205	35	9	was	be	AUX
eurjchem-205	35	10	diluted	dilute	VERB
eurjchem-205	35	11	with	with	ADP
eurjchem-205	35	12	water	water	NOUN
eurjchem-205	35	13	(	(	PUNCT
eurjchem-205	35	14	10	10	NUM
eurjchem-205	35	15	ml	ml	NOUN
eurjchem-205	35	16	)	)	PUNCT
eurjchem-205	35	17	and	and	CCONJ
eurjchem-205	35	18	product	product	NOUN
eurjchem-205	35	19	was	be	AUX
eurjchem-205	35	20	extracted	extract	VERB
eurjchem-205	35	21	using	use	VERB
eurjchem-205	35	22	ethyl	ethyl	PROPN
eurjchem-205	35	23	acetate	acetate	NOUN
eurjchem-205	35	24	(	(	PUNCT
eurjchem-205	35	25	3	3	NUM
eurjchem-205	35	26	x	x	SYM
eurjchem-205	35	27	30	30	NUM
eurjchem-205	35	28	ml	ml	NOUN
eurjchem-205	35	29	)	)	PUNCT
eurjchem-205	35	30	.	.	PUNCT
eurjchem-205	36	1	the	the	DET
eurjchem-205	36	2	combined	combine	VERB
eurjchem-205	36	3	organic	organic	ADJ
eurjchem-205	36	4	layer	layer	NOUN
eurjchem-205	36	5	was	be	AUX
eurjchem-205	36	6	dried	dry	VERB
eurjchem-205	36	7	over	over	ADP
eurjchem-205	36	8	anhydrous	anhydrous	ADJ
eurjchem-205	36	9	na2so4	na2so4	NOUN
eurjchem-205	36	10	and	and	CCONJ
eurjchem-205	36	11	evaporated	evaporate	VERB
eurjchem-205	36	12	under	under	ADP
eurjchem-205	36	13	reduced	reduce	VERB
eurjchem-205	36	14	pressure	pressure	NOUN
eurjchem-205	36	15	to	to	PART
eurjchem-205	36	16	afford	afford	VERB
eurjchem-205	36	17	a	a	DET
eurjchem-205	36	18	crude	crude	ADJ
eurjchem-205	36	19	product	product	NOUN
eurjchem-205	36	20	which	which	PRON
eurjchem-205	36	21	was	be	AUX
eurjchem-205	36	22	purified	purify	VERB
eurjchem-205	36	23	by	by	ADP
eurjchem-205	36	24	column	column	NOUN
eurjchem-205	36	25	chromatography	chromatography	NOUN
eurjchem-205	36	26	using	use	VERB
eurjchem-205	36	27	petroleum	petroleum	NOUN
eurjchem-205	36	28	ether	ether	NOUN
eurjchem-205	36	29	:	:	PUNCT
eurjchem-205	36	30	ethyl	ethyl	PROPN
eurjchem-205	36	31	acetate	acetate	PROPN
eurjchem-205	36	32	(	(	PUNCT
eurjchem-205	36	33	9:1	9:1	NUM
eurjchem-205	36	34	)	)	PUNCT
eurjchem-205	36	35	to	to	PART
eurjchem-205	36	36	obtain	obtain	VERB
eurjchem-205	36	37	1.21	1.21	NUM
eurjchem-205	36	38	g	g	NOUN
eurjchem-205	36	39	(	(	PUNCT
eurjchem-205	36	40	73	73	NUM
eurjchem-205	36	41	%	%	NOUN
eurjchem-205	36	42	)	)	PUNCT
eurjchem-205	36	43	of	of	ADP
eurjchem-205	36	44	the	the	DET
eurjchem-205	36	45	pure	pure	ADJ
eurjchem-205	36	46	methyl	methyl	NOUN
eurjchem-205	36	47	2‐methylquinoline‐3‐	2‐methylquinoline‐3‐	NUM
eurjchem-205	36	48	carboxylate	carboxylate	NOUN
eurjchem-205	36	49	(	(	PUNCT
eurjchem-205	36	50	3	3	NUM
eurjchem-205	36	51	)	)	PUNCT
eurjchem-205	36	52	as	as	ADP
eurjchem-205	36	53	white	white	PROPN
eurjchem-205	36	54	solid	solid	PROPN
eurjchem-205	36	55	.	.	PUNCT
eurjchem-205	37	1	m.p	m.p	PROPN
eurjchem-205	37	2	.	.	PROPN
eurjchem-205	37	3	:	:	PUNCT
eurjchem-205	37	4	67‐69	67‐69	NUM
eurjchem-205	37	5	oc	oc	PROPN
eurjchem-205	37	6	.	.	PUNCT
eurjchem-205	38	1	ir	ir	PROPN
eurjchem-205	38	2	(	(	PUNCT
eurjchem-205	38	3	kbr	kbr	PROPN
eurjchem-205	38	4	,	,	PUNCT
eurjchem-205	38	5	max	max	PROPN
eurjchem-205	38	6	,	,	PUNCT
eurjchem-205	38	7	cm‐1	cm‐1	PROPN
eurjchem-205	38	8	):	):	PUNCT
eurjchem-205	38	9	2951	2951	NUM
eurjchem-205	38	10	,	,	PUNCT
eurjchem-205	38	11	1726	1726	NUM
eurjchem-205	38	12	,	,	PUNCT
eurjchem-205	38	13	1621	1621	NUM
eurjchem-205	38	14	,	,	PUNCT
eurjchem-205	38	15	1565	1565	NUM
eurjchem-205	38	16	,	,	PUNCT
eurjchem-205	38	17	1489	1489	NUM
eurjchem-205	38	18	,	,	PUNCT
eurjchem-205	38	19	1438	1438	NUM
eurjchem-205	38	20	,	,	PUNCT
eurjchem-205	38	21	1278	1278	NUM
eurjchem-205	38	22	,	,	PUNCT
eurjchem-205	38	23	1200	1200	NUM
eurjchem-205	38	24	,	,	PUNCT
eurjchem-205	38	25	1127	1127	NUM
eurjchem-205	38	26	,	,	PUNCT
eurjchem-205	38	27	1064	1064	NUM
eurjchem-205	38	28	,	,	PUNCT
eurjchem-205	38	29	788	788	NUM
eurjchem-205	38	30	.	.	PUNCT
eurjchem-205	39	1	1h	1h	NUM
eurjchem-205	39	2	nmr	nmr	NOUN
eurjchem-205	39	3	(	(	PUNCT
eurjchem-205	39	4	200	200	NUM
eurjchem-205	39	5	mhz	mhz	NOUN
eurjchem-205	39	6	,	,	PUNCT
eurjchem-205	39	7	cdcl3	cdcl3	PROPN
eurjchem-205	39	8	,	,	PUNCT
eurjchem-205	39	9	δ	δ	PROPN
eurjchem-205	39	10	,	,	PUNCT
eurjchem-205	39	11	ppm	ppm	NUM
eurjchem-205	39	12	):	):	PUNCT
eurjchem-205	39	13	3.01	3.01	NUM
eurjchem-205	39	14	(	(	PUNCT
eurjchem-205	39	15	s	s	PROPN
eurjchem-205	39	16	,	,	PUNCT
eurjchem-205	39	17	3h	3h	NUM
eurjchem-205	39	18	,	,	PUNCT
eurjchem-205	39	19	ch3	ch3	PROPN
eurjchem-205	39	20	)	)	PUNCT
eurjchem-205	39	21	,	,	PUNCT
eurjchem-205	39	22	3.99	3.99	NUM
eurjchem-205	39	23	(	(	PUNCT
eurjchem-205	39	24	s	s	PROPN
eurjchem-205	39	25	,	,	PUNCT
eurjchem-205	39	26	3h	3h	NUM
eurjchem-205	39	27	,	,	PUNCT
eurjchem-205	39	28	och3	och3	ADJ
eurjchem-205	39	29	)	)	PUNCT
eurjchem-205	39	30	,	,	PUNCT
eurjchem-205	39	31	7.51‐7.59	7.51‐7.59	NUM
eurjchem-205	39	32	(	(	PUNCT
eurjchem-205	39	33	m	m	PROPN
eurjchem-205	39	34	,	,	PUNCT
eurjchem-205	39	35	1h	1h	NUM
eurjchem-205	39	36	,	,	PUNCT
eurjchem-205	39	37	arh	arh	ADJ
eurjchem-205	39	38	)	)	PUNCT
eurjchem-205	39	39	,	,	PUNCT
eurjchem-205	39	40	7.76‐7.89	7.76‐7.89	NUM
eurjchem-205	39	41	(	(	PUNCT
eurjchem-205	39	42	m	m	PROPN
eurjchem-205	39	43	,	,	PUNCT
eurjchem-205	39	44	2h	2h	NUM
eurjchem-205	39	45	,	,	PUNCT
eurjchem-205	39	46	arh	arh	ADJ
eurjchem-205	39	47	)	)	PUNCT
eurjchem-205	39	48	,	,	PUNCT
eurjchem-205	39	49	8.04‐8.08	8.04‐8.08	NUM
eurjchem-205	39	50	(	(	PUNCT
eurjchem-205	39	51	d	d	PROPN
eurjchem-205	39	52	,	,	PUNCT
eurjchem-205	39	53	j	j	PROPN
eurjchem-205	39	54	=	=	PROPN
eurjchem-205	39	55	8.49	8.49	NUM
eurjchem-205	39	56	hz	hz	NOUN
eurjchem-205	39	57	,	,	PUNCT
eurjchem-205	39	58	1h	1h	NUM
eurjchem-205	39	59	,	,	PUNCT
eurjchem-205	39	60	arh	arh	PROPN
eurjchem-205	39	61	)	)	PUNCT
eurjchem-205	39	62	,	,	PUNCT
eurjchem-205	39	63	8.76	8.76	NUM
eurjchem-205	39	64	(	(	PUNCT
eurjchem-205	39	65	s	s	PROPN
eurjchem-205	39	66	,	,	PUNCT
eurjchem-205	39	67	1h	1h	NUM
eurjchem-205	39	68	,	,	PUNCT
eurjchem-205	39	69	arh	arh	ADJ
eurjchem-205	39	70	)	)	PUNCT
eurjchem-205	39	71	.	.	PUNCT
eurjchem-205	40	1	13c	13c	NOUN
eurjchem-205	40	2	nmr	nmr	NOUN
eurjchem-205	40	3	(	(	PUNCT
eurjchem-205	40	4	50	50	NUM
eurjchem-205	40	5	mhz	mhz	NOUN
eurjchem-205	40	6	,	,	PUNCT
eurjchem-205	40	7			NUM
eurjchem-205	40	8	,	,	PUNCT
eurjchem-205	40	9	ppm	ppm	NUM
eurjchem-205	40	10	):	):	PUNCT
eurjchem-205	40	11	169.4	169.4	NUM
eurjchem-205	40	12	,	,	PUNCT
eurjchem-205	40	13	25.5	25.5	NUM
eurjchem-205	40	14	(	(	PUNCT
eurjchem-205	40	15	ch3	ch3	PROPN
eurjchem-205	40	16	)	)	PUNCT
eurjchem-205	40	17	,	,	PUNCT
eurjchem-205	40	18	52.2	52.2	NUM
eurjchem-205	40	19	(	(	PUNCT
eurjchem-205	40	20	c	c	NOUN
eurjchem-205	40	21	as	as	ADP
eurjchem-205	40	22	o‐ch3	o‐ch3	PROPN
eurjchem-205	40	23	)	)	PUNCT
eurjchem-205	40	24	,	,	PUNCT
eurjchem-205	40	25	123.3	123.3	NUM
eurjchem-205	40	26	,	,	PUNCT
eurjchem-205	40	27	125.6	125.6	NUM
eurjchem-205	40	28	,	,	PUNCT
eurjchem-205	40	29	126.2	126.2	NUM
eurjchem-205	40	30	,	,	PUNCT
eurjchem-205	40	31	128.3	128.3	NUM
eurjchem-205	40	32	,	,	PUNCT
eurjchem-205	40	33	131.6	131.6	NUM
eurjchem-205	40	34	,	,	PUNCT
eurjchem-205	40	35	139.9	139.9	NUM
eurjchem-205	40	36	,	,	PUNCT
eurjchem-205	40	37	148.48	148.48	NUM
eurjchem-205	40	38	,	,	PUNCT
eurjchem-205	40	39	158.39	158.39	NUM
eurjchem-205	40	40	(	(	PUNCT
eurjchem-205	40	41	chmethine	chmethine	PROPN
eurjchem-205	40	42	)	)	PUNCT
eurjchem-205	40	43	,	,	PUNCT
eurjchem-205	40	44	166.77	166.77	NUM
eurjchem-205	40	45	(	(	PUNCT
eurjchem-205	40	46	c	c	NOUN
eurjchem-205	40	47	as	as	ADP
eurjchem-205	40	48	c	c	NOUN
eurjchem-205	40	49	=	=	NOUN
eurjchem-205	40	50	o	o	NOUN
eurjchem-205	40	51	)	)	PUNCT
eurjchem-205	40	52	.	.	PUNCT
eurjchem-205	41	1	anal	anal	PROPN
eurjchem-205	41	2	.	.	PUNCT
eurjchem-205	41	3	calcd	calcd	NOUN
eurjchem-205	41	4	.	.	PUNCT
eurjchem-205	42	1	for	for	SCONJ
eurjchem-205	42	2	c12h11no2	c12h11no2	NOUN
eurjchem-205	42	3	(	(	PUNCT
eurjchem-205	42	4	%	%	INTJ
eurjchem-205	42	5	):	):	PUNCT
eurjchem-205	42	6	c	c	NOUN
eurjchem-205	42	7	,	,	PUNCT
eurjchem-205	42	8	71.63	71.63	NUM
eurjchem-205	42	9	;	;	PUNCT
eurjchem-205	42	10	h	h	X
eurjchem-205	42	11	,	,	PUNCT
eurjchem-205	42	12	5.51	5.51	NUM
eurjchem-205	42	13	;	;	PUNCT
eurjchem-205	42	14	n	n	CCONJ
eurjchem-205	42	15	,	,	PUNCT
eurjchem-205	42	16	6.96	6.96	NUM
eurjchem-205	42	17	.	.	PUNCT
eurjchem-205	42	18	found	find	VERB
eurjchem-205	42	19	:	:	PUNCT
eurjchem-205	43	1	c	c	X
eurjchem-205	43	2	,	,	PUNCT
eurjchem-205	43	3	71.51	71.51	NUM
eurjchem-205	43	4	;	;	PUNCT
eurjchem-205	43	5	h	h	NOUN
eurjchem-205	43	6	,	,	PUNCT
eurjchem-205	43	7	5.67	5.67	NUM
eurjchem-205	43	8	;	;	PUNCT
eurjchem-205	43	9	n	n	CCONJ
eurjchem-205	43	10	,	,	PUNCT
eurjchem-205	43	11	7.08	7.08	NUM
eurjchem-205	43	12	.	.	PUNCT
eurjchem-205	44	1	2.3	2.3	NUM
eurjchem-205	44	2	.	.	PUNCT
eurjchem-205	44	3	synthesis	synthesis	NOUN
eurjchem-205	44	4	of	of	ADP
eurjchem-205	44	5	methyl	methyl	NOUN
eurjchem-205	44	6	2‐formyl	2‐formyl	NUM
eurjchem-205	44	7	quionoline‐3‐carboxylate	quionoline‐3‐carboxylate	PROPN
eurjchem-205	44	8	(	(	PUNCT
eurjchem-205	44	9	4	4	NUM
eurjchem-205	44	10	)	)	PUNCT
eurjchem-205	44	11	a	a	DET
eurjchem-205	44	12	mixture	mixture	NOUN
eurjchem-205	44	13	of	of	ADP
eurjchem-205	44	14	methyl	methyl	NOUN
eurjchem-205	44	15	2‐methylquinoline‐3‐carboxylate	2‐methylquinoline‐3‐carboxylate	NUM
eurjchem-205	44	16	3	3	NUM
eurjchem-205	44	17	(	(	PUNCT
eurjchem-205	44	18	0.8	0.8	NUM
eurjchem-205	44	19	g	g	NOUN
eurjchem-205	44	20	,	,	PUNCT
eurjchem-205	44	21	4	4	NUM
eurjchem-205	44	22	mmol	mmol	NOUN
eurjchem-205	44	23	)	)	PUNCT
eurjchem-205	44	24	and	and	CCONJ
eurjchem-205	44	25	selenium	selenium	NOUN
eurjchem-205	44	26	dioxide	dioxide	NOUN
eurjchem-205	44	27	(	(	PUNCT
eurjchem-205	44	28	0.046	0.046	NUM
eurjchem-205	44	29	g	g	NOUN
eurjchem-205	44	30	,	,	PUNCT
eurjchem-205	44	31	4.2	4.2	NUM
eurjchem-205	44	32	mmol	mmol	NOUN
eurjchem-205	44	33	)	)	PUNCT
eurjchem-205	44	34	in	in	ADP
eurjchem-205	44	35	xylene	xylene	NOUN
eurjchem-205	44	36	(	(	PUNCT
eurjchem-205	44	37	25	25	NUM
eurjchem-205	44	38	ml	ml	NOUN
eurjchem-205	44	39	)	)	PUNCT
eurjchem-205	44	40	was	be	AUX
eurjchem-205	44	41	refluxed	refluxe	VERB
eurjchem-205	44	42	for	for	ADP
eurjchem-205	44	43	8	8	NUM
eurjchem-205	44	44	h.	h.	NOUN
eurjchem-205	44	45	the	the	DET
eurjchem-205	44	46	progress	progress	NOUN
eurjchem-205	44	47	of	of	ADP
eurjchem-205	44	48	reaction	reaction	NOUN
eurjchem-205	44	49	was	be	AUX
eurjchem-205	44	50	monitored	monitor	VERB
eurjchem-205	44	51	by	by	ADP
eurjchem-205	44	52	tlc	tlc	PROPN
eurjchem-205	44	53	.	.	PUNCT
eurjchem-205	45	1	after	after	ADP
eurjchem-205	45	2	completion	completion	NOUN
eurjchem-205	45	3	of	of	ADP
eurjchem-205	45	4	reaction	reaction	NOUN
eurjchem-205	45	5	solvent	solvent	NOUN
eurjchem-205	45	6	was	be	AUX
eurjchem-205	45	7	evaporated	evaporate	VERB
eurjchem-205	45	8	under	under	ADP
eurjchem-205	45	9	reduced	reduce	VERB
eurjchem-205	45	10	pressure	pressure	NOUN
eurjchem-205	45	11	to	to	PART
eurjchem-205	45	12	get	get	VERB
eurjchem-205	45	13	a	a	DET
eurjchem-205	45	14	blackish	blackish	ADJ
eurjchem-205	45	15	residue	residue	NOUN
eurjchem-205	45	16	and	and	CCONJ
eurjchem-205	45	17	the	the	DET
eurjchem-205	45	18	product	product	NOUN
eurjchem-205	45	19	was	be	AUX
eurjchem-205	45	20	extracted	extract	VERB
eurjchem-205	45	21	using	use	VERB
eurjchem-205	45	22	ethyl	ethyl	PROPN
eurjchem-205	45	23	acetate	acetate	NOUN
eurjchem-205	45	24	(	(	PUNCT
eurjchem-205	45	25	3	3	NUM
eurjchem-205	45	26	x	x	SYM
eurjchem-205	45	27	30	30	NUM
eurjchem-205	45	28	ml	ml	NOUN
eurjchem-205	45	29	)	)	PUNCT
eurjchem-205	45	30	.	.	PUNCT
eurjchem-205	46	1	the	the	DET
eurjchem-205	46	2	combined	combine	VERB
eurjchem-205	46	3	organic	organic	ADJ
eurjchem-205	46	4	layer	layer	NOUN
eurjchem-205	46	5	was	be	AUX
eurjchem-205	46	6	dried	dry	VERB
eurjchem-205	46	7	over	over	ADP
eurjchem-205	46	8	anhydrous	anhydrous	ADJ
eurjchem-205	46	9	na2so4	na2so4	NOUN
eurjchem-205	46	10	and	and	CCONJ
eurjchem-205	46	11	evaporated	evaporate	VERB
eurjchem-205	46	12	under	under	ADP
eurjchem-205	46	13	reduced	reduce	VERB
eurjchem-205	46	14	pressure	pressure	NOUN
eurjchem-205	46	15	to	to	PART
eurjchem-205	46	16	afford	afford	VERB
eurjchem-205	46	17	a	a	DET
eurjchem-205	46	18	crude	crude	ADJ
eurjchem-205	46	19	product	product	NOUN
eurjchem-205	46	20	which	which	PRON
eurjchem-205	46	21	was	be	AUX
eurjchem-205	46	22	purified	purify	VERB
eurjchem-205	46	23	by	by	ADP
eurjchem-205	46	24	column	column	NOUN
eurjchem-205	46	25	chromatography	chromatography	NOUN
eurjchem-205	46	26	using	use	VERB
eurjchem-205	46	27	petroleum	petroleum	NOUN
eurjchem-205	46	28	ether	ether	NOUN
eurjchem-205	46	29	:	:	PUNCT
eurjchem-205	46	30	ethyl	ethyl	PROPN
eurjchem-205	46	31	acetate	acetate	PROPN
eurjchem-205	46	32	(	(	PUNCT
eurjchem-205	46	33	8.5:1.5	8.5:1.5	NUM
eurjchem-205	46	34	)	)	PUNCT
eurjchem-205	46	35	to	to	PART
eurjchem-205	46	36	afford	afford	VERB
eurjchem-205	46	37	0.590	0.590	NUM
eurjchem-205	46	38	g	g	NOUN
eurjchem-205	46	39	(	(	PUNCT
eurjchem-205	46	40	69	69	NUM
eurjchem-205	46	41	%	%	NOUN
eurjchem-205	46	42	)	)	PUNCT
eurjchem-205	46	43	of	of	ADP
eurjchem-205	46	44	pure	pure	ADJ
eurjchem-205	46	45	methyl	methyl	NOUN
eurjchem-205	46	46	2‐formyl	2‐formyl	NUM
eurjchem-205	46	47	quionoline‐3‐carboxylate	quionoline‐3‐carboxylate	NOUN
eurjchem-205	46	48	4	4	NUM
eurjchem-205	46	49	as	as	ADP
eurjchem-205	46	50	dark	dark	ADJ
eurjchem-205	46	51	brown	brown	ADJ
eurjchem-205	46	52	viscous	viscous	ADJ
eurjchem-205	46	53	liquid	liquid	NOUN
eurjchem-205	46	54	.	.	PUNCT
eurjchem-205	47	1	ir	ir	PROPN
eurjchem-205	47	2	(	(	PUNCT
eurjchem-205	47	3	kbr	kbr	PROPN
eurjchem-205	47	4	,	,	PUNCT
eurjchem-205	47	5	max	max	PROPN
eurjchem-205	47	6	,	,	PUNCT
eurjchem-205	47	7	cm‐1	cm‐1	PROPN
eurjchem-205	47	8	):	):	PUNCT
eurjchem-205	47	9	3020	3020	NUM
eurjchem-205	47	10	,	,	PUNCT
eurjchem-205	47	11	2954	2954	NUM
eurjchem-205	47	12	,	,	PUNCT
eurjchem-205	47	13	2853	2853	NUM
eurjchem-205	47	14	,	,	PUNCT
eurjchem-205	47	15	1770	1770	NUM
eurjchem-205	47	16	,	,	PUNCT
eurjchem-205	47	17	1727	1727	NUM
eurjchem-205	47	18	,	,	PUNCT
eurjchem-205	47	19	1567	1567	NUM
eurjchem-205	47	20	,	,	PUNCT
eurjchem-205	47	21	1439	1439	NUM
eurjchem-205	47	22	,	,	PUNCT
eurjchem-205	47	23	1216	1216	NUM
eurjchem-205	47	24	,	,	PUNCT
eurjchem-205	47	25	1051	1051	NUM
eurjchem-205	47	26	,	,	PUNCT
eurjchem-205	47	27	945	945	NUM
eurjchem-205	47	28	,	,	PUNCT
eurjchem-205	47	29	756	756	NUM
eurjchem-205	47	30	,	,	PUNCT
eurjchem-205	47	31	667	667	NUM
eurjchem-205	47	32	.	.	PUNCT
eurjchem-205	48	1	1h	1h	NUM
eurjchem-205	48	2	nmr	nmr	NOUN
eurjchem-205	48	3	(	(	PUNCT
eurjchem-205	48	4	200	200	NUM
eurjchem-205	48	5	mhz	mhz	NOUN
eurjchem-205	48	6	,	,	PUNCT
eurjchem-205	48	7	cdcl3	cdcl3	PROPN
eurjchem-205	48	8	,	,	PUNCT
eurjchem-205	48	9	δ	δ	PROPN
eurjchem-205	48	10	,	,	PUNCT
eurjchem-205	48	11	ppm	ppm	NOUN
eurjchem-205	48	12	):	):	PUNCT
eurjchem-205	48	13	4.02	4.02	NUM
eurjchem-205	48	14	,	,	PUNCT
eurjchem-205	48	15	(	(	PUNCT
eurjchem-205	48	16	s	s	X
eurjchem-205	48	17	,	,	PUNCT
eurjchem-205	48	18	3h	3h	NUM
eurjchem-205	48	19	,	,	PUNCT
eurjchem-205	48	20	och3	och3	ADJ
eurjchem-205	48	21	)	)	PUNCT
eurjchem-205	48	22	,	,	PUNCT
eurjchem-205	48	23	7.71‐7.79	7.71‐7.79	NUM
eurjchem-205	48	24	(	(	PUNCT
eurjchem-205	48	25	m	m	PROPN
eurjchem-205	48	26	,	,	PUNCT
eurjchem-205	48	27	1h	1h	NUM
eurjchem-205	48	28	,	,	PUNCT
eurjchem-205	48	29	arh	arh	ADJ
eurjchem-205	48	30	)	)	PUNCT
eurjchem-205	48	31	,	,	PUNCT
eurjchem-205	48	32	7.87‐7.99	7.87‐7.99	NUM
eurjchem-205	48	33	(	(	PUNCT
eurjchem-205	48	34	m	m	PROPN
eurjchem-205	48	35	,	,	PUNCT
eurjchem-205	48	36	2h	2h	NUM
eurjchem-205	48	37	,	,	PUNCT
eurjchem-205	48	38	arh	arh	ADJ
eurjchem-205	48	39	)	)	PUNCT
eurjchem-205	48	40	,	,	PUNCT
eurjchem-205	48	41	8.28‐8.32	8.28‐8.32	NUM
eurjchem-205	48	42	(	(	PUNCT
eurjchem-205	48	43	d	d	NOUN
eurjchem-205	48	44	,	,	PUNCT
eurjchem-205	48	45	j	j	PROPN
eurjchem-205	48	46	=	=	PROPN
eurjchem-205	48	47	8.49	8.49	NUM
eurjchem-205	48	48	hz	hz	NOUN
eurjchem-205	48	49	,	,	PUNCT
eurjchem-205	48	50	1h	1h	NUM
eurjchem-205	48	51	,	,	PUNCT
eurjchem-205	48	52	arh	arh	PROPN
eurjchem-205	48	53	)	)	PUNCT
eurjchem-205	48	54	,	,	PUNCT
eurjchem-205	48	55	8.61	8.61	NUM
eurjchem-205	48	56	(	(	PUNCT
eurjchem-205	48	57	s	s	PROPN
eurjchem-205	48	58	,	,	PUNCT
eurjchem-205	48	59	1h	1h	NUM
eurjchem-205	48	60	,	,	PUNCT
eurjchem-205	48	61	arh	arh	PROPN
eurjchem-205	48	62	)	)	PUNCT
eurjchem-205	48	63	,	,	PUNCT
eurjchem-205	48	64	10.41	10.41	NUM
eurjchem-205	48	65	(	(	PUNCT
eurjchem-205	48	66	s	s	PROPN
eurjchem-205	48	67	,	,	PUNCT
eurjchem-205	48	68	1h	1h	NUM
eurjchem-205	48	69	,	,	PUNCT
eurjchem-205	48	70	cho	cho	NOUN
eurjchem-205	48	71	)	)	PUNCT
eurjchem-205	48	72	.	.	PUNCT
eurjchem-205	49	1	13c	13c	NOUN
eurjchem-205	49	2	nmr	nmr	NOUN
eurjchem-205	49	3	(	(	PUNCT
eurjchem-205	49	4	50	50	NUM
eurjchem-205	49	5	mhz	mhz	NOUN
eurjchem-205	49	6	,	,	PUNCT
eurjchem-205	49	7			NUM
eurjchem-205	49	8	,	,	PUNCT
eurjchem-205	49	9	ppm	ppm	NUM
eurjchem-205	49	10	):	):	PUNCT
eurjchem-205	49	11	53	53	NUM
eurjchem-205	49	12	(	(	PUNCT
eurjchem-205	49	13	o‐ch3	o‐ch3	PROPN
eurjchem-205	49	14	)	)	PUNCT
eurjchem-205	49	15	,	,	PUNCT
eurjchem-205	49	16	124.4	124.4	NUM
eurjchem-205	49	17	,	,	PUNCT
eurjchem-205	49	18	127.8	127.8	NUM
eurjchem-205	49	19	,	,	PUNCT
eurjchem-205	49	20	128.3	128.3	NUM
eurjchem-205	49	21	,	,	PUNCT
eurjchem-205	49	22	129.7	129.7	NUM
eurjchem-205	49	23	,	,	PUNCT
eurjchem-205	49	24	130.4	130.4	NUM
eurjchem-205	49	25	,	,	PUNCT
eurjchem-205	49	26	132.1	132.1	NUM
eurjchem-205	49	27	,	,	PUNCT
eurjchem-205	49	28	138.5	138.5	NUM
eurjchem-205	49	29	,	,	PUNCT
eurjchem-205	49	30	147.9	147.9	NUM
eurjchem-205	49	31	,	,	PUNCT
eurjchem-205	49	32	151.2	151.2	NUM
eurjchem-205	49	33	(	(	PUNCT
eurjchem-205	49	34	chmethine	chmethine	PROPN
eurjchem-205	49	35	)	)	PUNCT
eurjchem-205	49	36	,	,	PUNCT
eurjchem-205	49	37	166.9	166.9	NUM
eurjchem-205	49	38	(	(	PUNCT
eurjchem-205	49	39	cester	cester	NOUN
eurjchem-205	49	40	as	as	ADP
eurjchem-205	49	41	c	c	NOUN
eurjchem-205	49	42	=	=	NOUN
eurjchem-205	49	43	o	o	NOUN
eurjchem-205	49	44	)	)	PUNCT
eurjchem-205	49	45	,	,	PUNCT
eurjchem-205	49	46	191.5	191.5	NUM
eurjchem-205	49	47	(	(	PUNCT
eurjchem-205	49	48	caldehyde	caldehyde	NOUN
eurjchem-205	49	49	as	as	ADP
eurjchem-205	49	50	c	c	NOUN
eurjchem-205	49	51	=	=	NOUN
eurjchem-205	49	52	o	o	NOUN
eurjchem-205	49	53	)	)	PUNCT
eurjchem-205	49	54	.	.	PUNCT
eurjchem-205	50	1	anal	anal	PROPN
eurjchem-205	50	2	.	.	PUNCT
eurjchem-205	50	3	calcd	calcd	NOUN
eurjchem-205	50	4	.	.	PUNCT
eurjchem-205	51	1	for	for	ADP
eurjchem-205	51	2	c12h9no3	c12h9no3	NOUN
eurjchem-205	51	3	(	(	PUNCT
eurjchem-205	51	4	%	%	INTJ
eurjchem-205	51	5	):	):	PUNCT
eurjchem-205	51	6	c	c	NOUN
eurjchem-205	51	7	,	,	PUNCT
eurjchem-205	51	8	66.97	66.97	NUM
eurjchem-205	51	9	;	;	PUNCT
eurjchem-205	51	10	h	h	NOUN
eurjchem-205	51	11	,	,	PUNCT
eurjchem-205	51	12	4.22	4.22	NUM
eurjchem-205	51	13	;	;	PUNCT
eurjchem-205	51	14	n	n	CCONJ
eurjchem-205	51	15	,	,	PUNCT
eurjchem-205	51	16	6.51	6.51	NUM
eurjchem-205	51	17	.	.	PUNCT
eurjchem-205	52	1	found	find	VERB
eurjchem-205	52	2	:	:	PUNCT
eurjchem-205	53	1	c	c	X
eurjchem-205	53	2	,	,	PUNCT
eurjchem-205	53	3	66.87	66.87	NUM
eurjchem-205	53	4	;	;	PUNCT
eurjchem-205	54	1	h	h	NOUN
eurjchem-205	54	2	,	,	PUNCT
eurjchem-205	54	3	4.35	4.35	NUM
eurjchem-205	54	4	;	;	PUNCT
eurjchem-205	54	5	n	n	CCONJ
eurjchem-205	54	6	,	,	PUNCT
eurjchem-205	54	7	6.67	6.67	NUM
eurjchem-205	54	8	.	.	NOUN
eurjchem-205	54	9	2.4	2.4	NUM
eurjchem-205	54	10	.	.	PUNCT
eurjchem-205	55	1	synthesis	synthesis	NOUN
eurjchem-205	55	2	of	of	ADP
eurjchem-205	55	3	methyl	methyl	NOUN
eurjchem-205	55	4	2‐(4‐oxo‐3,4‐dihydroquinazolin‐2‐yl	2‐(4‐oxo‐3,4‐dihydroquinazolin‐2‐yl	NUM
eurjchem-205	55	5	)	)	PUNCT
eurjchem-205	55	6	quioline‐3‐carboxylate	quioline‐3‐carboxylate	NUM
eurjchem-205	55	7	(	(	PUNCT
eurjchem-205	55	8	6	6	NUM
eurjchem-205	55	9	)	)	PUNCT
eurjchem-205	55	10	a	a	DET
eurjchem-205	55	11	mixture	mixture	NOUN
eurjchem-205	55	12	of	of	ADP
eurjchem-205	55	13	methyl	methyl	NOUN
eurjchem-205	55	14	2‐formyl	2‐formyl	PROPN
eurjchem-205	55	15	quionoline‐3‐carboxylate	quionoline‐3‐carboxylate	NUM
eurjchem-205	55	16	4	4	NUM
eurjchem-205	55	17	(	(	PUNCT
eurjchem-205	55	18	0.4	0.4	NUM
eurjchem-205	55	19	g	g	NOUN
eurjchem-205	55	20	,	,	PUNCT
eurjchem-205	55	21	1.86	1.86	NUM
eurjchem-205	55	22	mmol	mmol	NOUN
eurjchem-205	55	23	)	)	PUNCT
eurjchem-205	55	24	,	,	PUNCT
eurjchem-205	55	25	anthranilamide	anthranilamide	ADV
eurjchem-205	55	26	5	5	NUM
eurjchem-205	55	27	(	(	PUNCT
eurjchem-205	55	28	0.265	0.265	NUM
eurjchem-205	55	29	g	g	NOUN
eurjchem-205	55	30	,	,	PUNCT
eurjchem-205	55	31	1.96	1.96	NUM
eurjchem-205	55	32	mmol	mmol	NOUN
eurjchem-205	55	33	)	)	PUNCT
eurjchem-205	55	34	,	,	PUNCT
eurjchem-205	55	35	ferric	ferric	ADJ
eurjchem-205	55	36	chloride	chloride	NOUN
eurjchem-205	55	37	hexahydrate	hexahydrate	NOUN
eurjchem-205	55	38	(	(	PUNCT
eurjchem-205	55	39	1.05	1.05	NUM
eurjchem-205	55	40	g	g	NOUN
eurjchem-205	55	41	,	,	PUNCT
eurjchem-205	55	42	3.9	3.9	NUM
eurjchem-205	55	43	mmol	mmol	NOUN
eurjchem-205	55	44	)	)	PUNCT
eurjchem-205	55	45	in	in	ADP
eurjchem-205	55	46	water	water	NOUN
eurjchem-205	55	47	(	(	PUNCT
eurjchem-205	55	48	20	20	NUM
eurjchem-205	55	49	ml	ml	NOUN
eurjchem-205	55	50	)	)	PUNCT
eurjchem-205	55	51	was	be	AUX
eurjchem-205	55	52	refluxed	refluxe	VERB
eurjchem-205	55	53	for	for	ADP
eurjchem-205	55	54	4	4	NUM
eurjchem-205	55	55	h.	h.	NOUN
eurjchem-205	55	56	the	the	DET
eurjchem-205	55	57	progress	progress	NOUN
eurjchem-205	55	58	of	of	ADP
eurjchem-205	55	59	reaction	reaction	NOUN
eurjchem-205	55	60	was	be	AUX
eurjchem-205	55	61	monitored	monitor	VERB
eurjchem-205	55	62	by	by	ADP
eurjchem-205	55	63	tlc	tlc	PROPN
eurjchem-205	55	64	.	.	PUNCT
eurjchem-205	56	1	after	after	ADP
eurjchem-205	56	2	completion	completion	NOUN
eurjchem-205	56	3	of	of	ADP
eurjchem-205	56	4	reaction	reaction	NOUN
eurjchem-205	56	5	,	,	PUNCT
eurjchem-205	56	6	the	the	DET
eurjchem-205	56	7	reaction	reaction	NOUN
eurjchem-205	56	8	mixture	mixture	NOUN
eurjchem-205	56	9	was	be	AUX
eurjchem-205	56	10	extracted	extract	VERB
eurjchem-205	56	11	using	use	VERB
eurjchem-205	56	12	ethyl	ethyl	PROPN
eurjchem-205	56	13	acetate	acetate	NOUN
eurjchem-205	56	14	(	(	PUNCT
eurjchem-205	56	15	3	3	NUM
eurjchem-205	56	16	x	x	SYM
eurjchem-205	56	17	30	30	NUM
eurjchem-205	56	18	ml	ml	NOUN
eurjchem-205	56	19	)	)	PUNCT
eurjchem-205	56	20	.	.	PUNCT
eurjchem-205	57	1	the	the	DET
eurjchem-205	57	2	combined	combine	VERB
eurjchem-205	57	3	organic	organic	ADJ
eurjchem-205	57	4	layer	layer	NOUN
eurjchem-205	57	5	was	be	AUX
eurjchem-205	57	6	dried	dry	VERB
eurjchem-205	57	7	over	over	ADP
eurjchem-205	57	8	anhydrous	anhydrous	ADJ
eurjchem-205	57	9	na2so4	na2so4	NOUN
eurjchem-205	57	10	and	and	CCONJ
eurjchem-205	57	11	evaporated	evaporate	VERB
eurjchem-205	57	12	under	under	ADP
eurjchem-205	57	13	reduced	reduce	VERB
eurjchem-205	57	14	pressure	pressure	NOUN
eurjchem-205	57	15	to	to	PART
eurjchem-205	57	16	afford	afford	VERB
eurjchem-205	57	17	a	a	DET
eurjchem-205	57	18	crude	crude	ADJ
eurjchem-205	57	19	product	product	NOUN
eurjchem-205	57	20	which	which	PRON
eurjchem-205	57	21	was	be	AUX
eurjchem-205	57	22	purified	purify	VERB
eurjchem-205	57	23	by	by	ADP
eurjchem-205	57	24	column	column	NOUN
eurjchem-205	57	25	chromatography	chromatography	NOUN
eurjchem-205	57	26	using	use	VERB
eurjchem-205	57	27	petroleum	petroleum	NOUN
eurjchem-205	57	28	ether	ether	NOUN
eurjchem-205	57	29	:	:	PUNCT
eurjchem-205	57	30	ethyl	ethyl	PROPN
eurjchem-205	57	31	acetate	acetate	PROPN
eurjchem-205	57	32	(	(	PUNCT
eurjchem-205	57	33	8:2	8:2	NUM
eurjchem-205	57	34	)	)	PUNCT
eurjchem-205	57	35	to	to	PART
eurjchem-205	57	36	obtain	obtain	VERB
eurjchem-205	57	37	0.47	0.47	NUM
eurjchem-205	57	38	g	g	NOUN
eurjchem-205	57	39	(	(	PUNCT
eurjchem-205	57	40	76	76	NUM
eurjchem-205	57	41	%	%	NOUN
eurjchem-205	57	42	)	)	PUNCT
eurjchem-205	57	43	of	of	ADP
eurjchem-205	57	44	the	the	DET
eurjchem-205	57	45	pure	pure	ADJ
eurjchem-205	57	46	methyl	methyl	NOUN
eurjchem-205	57	47	2‐	2‐	NUM
eurjchem-205	57	48	(	(	PUNCT
eurjchem-205	57	49	4‐oxo‐3,4‐dihydroquinazolin‐2‐yl	4‐oxo‐3,4‐dihydroquinazolin‐2‐yl	NUM
eurjchem-205	57	50	)	)	PUNCT
eurjchem-205	57	51	quioline‐3‐carboxylate	quioline‐3‐carboxylate	NUM
eurjchem-205	57	52	6	6	NUM
eurjchem-205	57	53	as	as	ADP
eurjchem-205	57	54	a	a	DET
eurjchem-205	57	55	white	white	ADJ
eurjchem-205	57	56	solid	solid	NOUN
eurjchem-205	57	57	.	.	PUNCT
eurjchem-205	58	1	m.p	m.p	PROPN
eurjchem-205	58	2	.	.	PROPN
eurjchem-205	58	3	:	:	PUNCT
eurjchem-205	59	1	226‐227	226‐227	NUM
eurjchem-205	59	2	oc	oc	PROPN
eurjchem-205	59	3	.	.	PROPN
eurjchem-205	59	4	ir	ir	PROPN
eurjchem-205	59	5	(	(	PUNCT
eurjchem-205	59	6	kbr	kbr	PROPN
eurjchem-205	59	7	,	,	PUNCT
eurjchem-205	59	8	max	max	PROPN
eurjchem-205	59	9	,	,	PUNCT
eurjchem-205	59	10	cm‐1	cm‐1	PROPN
eurjchem-205	59	11	):	):	PUNCT
eurjchem-205	59	12	3331	3331	NUM
eurjchem-205	59	13	,	,	PUNCT
eurjchem-205	59	14	119	119	NUM
eurjchem-205	59	15	,	,	PUNCT
eurjchem-205	59	16	2926	2926	NUM
eurjchem-205	59	17	,	,	PUNCT
eurjchem-205	59	18	2854	2854	NUM
eurjchem-205	59	19	,	,	PUNCT
eurjchem-205	59	20	1731	1731	NUM
eurjchem-205	59	21	,	,	PUNCT
eurjchem-205	59	22	1681	1681	NUM
eurjchem-205	59	23	,	,	PUNCT
eurjchem-205	59	24	1608	1608	NUM
eurjchem-205	59	25	,	,	PUNCT
eurjchem-205	59	26	1469	1469	NUM
eurjchem-205	59	27	,	,	PUNCT
eurjchem-205	59	28	1406	1406	NUM
eurjchem-205	59	29	,	,	PUNCT
eurjchem-205	59	30	1215	1215	NUM
eurjchem-205	59	31	,	,	PUNCT
eurjchem-205	59	32	1051	1051	NUM
eurjchem-205	59	33	,	,	PUNCT
eurjchem-205	59	34	902	902	NUM
eurjchem-205	59	35	,	,	PUNCT
eurjchem-205	59	36	757	757	NUM
eurjchem-205	59	37	,	,	PUNCT
eurjchem-205	59	38	668	668	NUM
eurjchem-205	59	39	.	.	NOUN
eurjchem-205	59	40	1h	1h	NUM
eurjchem-205	59	41	nmr	nmr	NOUN
eurjchem-205	59	42	(	(	PUNCT
eurjchem-205	59	43	200	200	NUM
eurjchem-205	59	44	mhz	mhz	NOUN
eurjchem-205	59	45	,	,	PUNCT
eurjchem-205	59	46	cdcl3	cdcl3	PROPN
eurjchem-205	59	47	,	,	PUNCT
eurjchem-205	59	48	δ	δ	PROPN
eurjchem-205	59	49	,	,	PUNCT
eurjchem-205	59	50	ppm	ppm	NOUN
eurjchem-205	59	51	):	):	PUNCT
eurjchem-205	59	52	4.04	4.04	NUM
eurjchem-205	59	53	(	(	PUNCT
eurjchem-205	59	54	s	s	NOUN
eurjchem-205	59	55	3h	3h	NUM
eurjchem-205	59	56	,	,	PUNCT
eurjchem-205	59	57	och3	och3	ADJ
eurjchem-205	59	58	)	)	PUNCT
eurjchem-205	59	59	,	,	PUNCT
eurjchem-205	59	60	7.50‐7.58	7.50‐7.58	NUM
eurjchem-205	59	61	(	(	PUNCT
eurjchem-205	59	62	m	m	PROPN
eurjchem-205	59	63	,	,	PUNCT
eurjchem-205	59	64	1h	1h	NUM
eurjchem-205	59	65	,	,	PUNCT
eurjchem-205	59	66	arh	arh	ADJ
eurjchem-205	59	67	)	)	PUNCT
eurjchem-205	59	68	,	,	PUNCT
eurjchem-205	59	69	7.65‐7.81	7.65‐7.81	NUM
eurjchem-205	59	70	(	(	PUNCT
eurjchem-205	59	71	m	m	PROPN
eurjchem-205	59	72	,	,	PUNCT
eurjchem-205	59	73	3h	3h	NUM
eurjchem-205	59	74	,	,	PUNCT
eurjchem-205	59	75	arh	arh	PROPN
eurjchem-205	59	76	)	)	PUNCT
eurjchem-205	59	77	,	,	PUNCT
eurjchem-205	59	78	7.83‐7.94	7.83‐7.94	NUM
eurjchem-205	59	79	(	(	PUNCT
eurjchem-205	59	80	m	m	PROPN
eurjchem-205	59	81	,	,	PUNCT
eurjchem-205	59	82	2h	2h	NUM
eurjchem-205	59	83	,	,	PUNCT
eurjchem-205	59	84	arh	arh	ADJ
eurjchem-205	59	85	)	)	PUNCT
eurjchem-205	59	86	,	,	PUNCT
eurjchem-205	59	87	8.16‐8.20	8.16‐8.20	NUM
eurjchem-205	59	88	(	(	PUNCT
eurjchem-205	59	89	d	d	PROPN
eurjchem-205	59	90	,	,	PUNCT
eurjchem-205	59	91	j	j	PROPN
eurjchem-205	59	92	=	=	PROPN
eurjchem-205	59	93	8.42	8.42	NUM
eurjchem-205	59	94	hz	hz	NOUN
eurjchem-205	59	95	,	,	PUNCT
eurjchem-205	59	96	1h	1h	NUM
eurjchem-205	59	97	,	,	PUNCT
eurjchem-205	59	98	arh	arh	ADJ
eurjchem-205	59	99	)	)	PUNCT
eurjchem-205	59	100	,	,	PUNCT
eurjchem-205	59	101	8.35‐8.38	8.35‐8.38	NUM
eurjchem-205	59	102	(	(	PUNCT
eurjchem-205	59	103	d	d	NOUN
eurjchem-205	59	104	,	,	PUNCT
eurjchem-205	59	105	j	j	PROPN
eurjchem-205	59	106	=	=	PROPN
eurjchem-205	59	107	6.58	6.58	NUM
eurjchem-205	59	108	hz	hz	NOUN
eurjchem-205	59	109	,	,	PUNCT
eurjchem-205	59	110	2h	2h	NUM
eurjchem-205	59	111	,	,	PUNCT
eurjchem-205	59	112	arh	arh	ADJ
eurjchem-205	59	113	)	)	PUNCT
eurjchem-205	59	114	,	,	PUNCT
eurjchem-205	59	115	11.01	11.01	NUM
eurjchem-205	59	116	(	(	PUNCT
eurjchem-205	59	117	bs	bs	PROPN
eurjchem-205	59	118	,	,	PUNCT
eurjchem-205	59	119	1h	1h	NUM
eurjchem-205	59	120	,	,	PUNCT
eurjchem-205	59	121	nh	nh	PROPN
eurjchem-205	59	122	)	)	PUNCT
eurjchem-205	59	123	.	.	PUNCT
eurjchem-205	60	1	13c	13c	NOUN
eurjchem-205	60	2	nmr	nmr	NOUN
eurjchem-205	60	3	(	(	PUNCT
eurjchem-205	60	4	50	50	NUM
eurjchem-205	60	5	mhz	mhz	NOUN
eurjchem-205	60	6	,	,	PUNCT
eurjchem-205	60	7			NUM
eurjchem-205	60	8	,	,	PUNCT
eurjchem-205	60	9	ppm	ppm	NUM
eurjchem-205	60	10	):	):	PUNCT
eurjchem-205	60	11	52.8	52.8	NUM
eurjchem-205	60	12	(	(	PUNCT
eurjchem-205	60	13	o‐ch3	o‐ch3	PROPN
eurjchem-205	60	14	)	)	PUNCT
eurjchem-205	60	15	,	,	PUNCT
eurjchem-205	60	16	122.4	122.4	NUM
eurjchem-205	60	17	,	,	PUNCT
eurjchem-205	60	18	126.5	126.5	NUM
eurjchem-205	60	19	,	,	PUNCT
eurjchem-205	60	20	126.7	126.7	NUM
eurjchem-205	60	21	,	,	PUNCT
eurjchem-205	60	22	127.5	127.5	NUM
eurjchem-205	60	23	,	,	PUNCT
eurjchem-205	60	24	127.8	127.8	NUM
eurjchem-205	60	25	,	,	PUNCT
eurjchem-205	60	26	127.9	127.9	NUM
eurjchem-205	60	27	,	,	PUNCT
eurjchem-205	60	28	128.0	128.0	NUM
eurjchem-205	60	29	,	,	PUNCT
eurjchem-205	60	30	129.1	129.1	NUM
eurjchem-205	60	31	,	,	PUNCT
eurjchem-205	60	32	129.5	129.5	NUM
eurjchem-205	60	33	,	,	PUNCT
eurjchem-205	60	34	131.6	131.6	NUM
eurjchem-205	60	35	,	,	PUNCT
eurjchem-205	60	36	137.5	137.5	NUM
eurjchem-205	60	37	,	,	PUNCT
eurjchem-205	60	38	136.9	136.9	NUM
eurjchem-205	60	39	,	,	PUNCT
eurjchem-205	60	40	144.6	144.6	NUM
eurjchem-205	60	41	,	,	PUNCT
eurjchem-205	60	42	146.4	146.4	NUM
eurjchem-205	60	43	,	,	PUNCT
eurjchem-205	60	44	147.6	147.6	NUM
eurjchem-205	60	45	,	,	PUNCT
eurjchem-205	60	46	148.3	148.3	NUM
eurjchem-205	60	47	(	(	PUNCT
eurjchem-205	60	48	chmethine	chmethine	PROPN
eurjchem-205	60	49	)	)	PUNCT
eurjchem-205	60	50	,	,	PUNCT
eurjchem-205	60	51	161.2	161.2	NUM
eurjchem-205	60	52	(	(	PUNCT
eurjchem-205	60	53	c	c	NOUN
eurjchem-205	60	54	as	as	ADP
eurjchem-205	60	55	c	c	NOUN
eurjchem-205	60	56	=	=	NOUN
eurjchem-205	60	57	o	o	NOUN
eurjchem-205	60	58	)	)	PUNCT
eurjchem-205	60	59	,	,	PUNCT
eurjchem-205	60	60	168.88	168.88	NUM
eurjchem-205	60	61	(	(	PUNCT
eurjchem-205	60	62	cester	cester	NOUN
eurjchem-205	60	63	as	as	ADP
eurjchem-205	60	64	c	c	NOUN
eurjchem-205	60	65	=	=	NOUN
eurjchem-205	60	66	o	o	NOUN
eurjchem-205	60	67	)	)	PUNCT
eurjchem-205	60	68	.	.	PUNCT
eurjchem-205	61	1	anal	anal	PROPN
eurjchem-205	61	2	.	.	PUNCT
eurjchem-205	61	3	calcd	calcd	NOUN
eurjchem-205	61	4	.	.	PUNCT
eurjchem-205	62	1	for	for	ADP
eurjchem-205	62	2	c19h13n3o3	c19h13n3o3	PROPN
eurjchem-205	62	3	(	(	PUNCT
eurjchem-205	62	4	%	%	INTJ
eurjchem-205	62	5	):	):	PUNCT
eurjchem-205	62	6	c	c	NOUN
eurjchem-205	62	7	,	,	PUNCT
eurjchem-205	62	8	68.88	68.88	NUM
eurjchem-205	62	9	;	;	PUNCT
eurjchem-205	62	10	h	h	NOUN
eurjchem-205	62	11	,	,	PUNCT
eurjchem-205	62	12	3.95	3.95	NUM
eurjchem-205	62	13	;	;	PUNCT
eurjchem-205	62	14	n	n	CCONJ
eurjchem-205	62	15	,	,	PUNCT
eurjchem-205	62	16	12.68	12.68	NUM
eurjchem-205	62	17	.	.	PUNCT
eurjchem-205	62	18	found	find	VERB
eurjchem-205	62	19	:	:	PUNCT
eurjchem-205	63	1	c	c	X
eurjchem-205	63	2	,	,	PUNCT
eurjchem-205	63	3	68.76	68.76	NUM
eurjchem-205	63	4	;	;	PUNCT
eurjchem-205	63	5	h	h	NOUN
eurjchem-205	63	6	,	,	PUNCT
eurjchem-205	63	7	3.81	3.81	NUM
eurjchem-205	63	8	;	;	PUNCT
eurjchem-205	63	9	n	n	CCONJ
eurjchem-205	63	10	,	,	PUNCT
eurjchem-205	63	11	12.81	12.81	NUM
eurjchem-205	63	12	.	.	PUNCT
eurjchem-205	64	1	2.5	2.5	NUM
eurjchem-205	64	2	.	.	PUNCT
eurjchem-205	64	3	synthesis	synthesis	NOUN
eurjchem-205	64	4	of	of	ADP
eurjchem-205	64	5	2‐(3‐(hydroxylmethyl)quinolin‐2‐yl	2‐(3‐(hydroxylmethyl)quinolin‐2‐yl	NOUN
eurjchem-205	64	6	)	)	PUNCT
eurjchem-205	64	7	quinozoline‐4(3h)‐one	quinozoline‐4(3h)‐one	NOUN
eurjchem-205	64	8	(	(	PUNCT
eurjchem-205	64	9	7	7	NUM
eurjchem-205	64	10	)	)	PUNCT
eurjchem-205	64	11	to	to	ADP
eurjchem-205	64	12	a	a	DET
eurjchem-205	64	13	well	well	ADV
eurjchem-205	64	14	stirred	stir	VERB
eurjchem-205	64	15	solution	solution	NOUN
eurjchem-205	64	16	of	of	ADP
eurjchem-205	64	17	methyl	methyl	NOUN
eurjchem-205	64	18	2‐(4‐oxo‐3,4‐	2‐(4‐oxo‐3,4‐	NUM
eurjchem-205	64	19	dihydroquinazolin‐2‐yl)quioline‐3‐carboxylate	dihydroquinazolin‐2‐yl)quioline‐3‐carboxylate	NOUN
eurjchem-205	64	20	6	6	NUM
eurjchem-205	64	21	(	(	PUNCT
eurjchem-205	64	22	0.165	0.165	NUM
eurjchem-205	64	23	g	g	NOUN
eurjchem-205	64	24	,	,	PUNCT
eurjchem-205	64	25	0.5	0.5	NUM
eurjchem-205	64	26	mmol	mmol	NOUN
eurjchem-205	64	27	)	)	PUNCT
eurjchem-205	64	28	in	in	ADP
eurjchem-205	64	29	ethanol	ethanol	NOUN
eurjchem-205	64	30	(	(	PUNCT
eurjchem-205	64	31	5	5	NUM
eurjchem-205	64	32	ml	ml	NOUN
eurjchem-205	64	33	)	)	PUNCT
eurjchem-205	64	34	was	be	AUX
eurjchem-205	64	35	added	add	VERB
eurjchem-205	64	36	cacl2	cacl2	NOUN
eurjchem-205	64	37	(	(	PUNCT
eurjchem-205	64	38	0.273	0.273	NUM
eurjchem-205	64	39	g	g	NOUN
eurjchem-205	64	40	,	,	PUNCT
eurjchem-205	64	41	2.5	2.5	NUM
eurjchem-205	64	42	mmol	mmol	NOUN
eurjchem-205	64	43	)	)	PUNCT
eurjchem-205	64	44	and	and	CCONJ
eurjchem-205	64	45	the	the	DET
eurjchem-205	64	46	resulting	result	VERB
eurjchem-205	64	47	solution	solution	NOUN
eurjchem-205	64	48	was	be	AUX
eurjchem-205	64	49	stirred	stir	VERB
eurjchem-205	64	50	for	for	ADP
eurjchem-205	64	51	15	15	NUM
eurjchem-205	64	52	min	min	NOUN
eurjchem-205	64	53	.	.	PROPN
eurjchem-205	64	54	finally	finally	ADV
eurjchem-205	64	55	powdered	powder	VERB
eurjchem-205	64	56	sodium	sodium	NOUN
eurjchem-205	64	57	borohydride	borohydride	NOUN
eurjchem-205	64	58	(	(	PUNCT
eurjchem-205	64	59	0.094	0.094	NUM
eurjchem-205	64	60	g	g	NOUN
eurjchem-205	64	61	,	,	PUNCT
eurjchem-205	64	62	2.5	2.5	NUM
eurjchem-205	64	63	mmol	mmol	NOUN
eurjchem-205	64	64	)	)	PUNCT
eurjchem-205	64	65	was	be	AUX
eurjchem-205	64	66	then	then	ADV
eurjchem-205	64	67	added	add	VERB
eurjchem-205	64	68	slowly	slowly	ADV
eurjchem-205	64	69	in	in	ADP
eurjchem-205	64	70	three	three	NUM
eurjchem-205	64	71	portions	portion	NOUN
eurjchem-205	64	72	and	and	CCONJ
eurjchem-205	64	73	the	the	DET
eurjchem-205	64	74	reaction	reaction	NOUN
eurjchem-205	64	75	mixture	mixture	NOUN
eurjchem-205	64	76	further	far	ADV
eurjchem-205	64	77	stirred	stir	VERB
eurjchem-205	64	78	at	at	ADP
eurjchem-205	64	79	room	room	NOUN
eurjchem-205	64	80	temperature	temperature	NOUN
eurjchem-205	64	81	for	for	ADP
eurjchem-205	64	82	2	2	NUM
eurjchem-205	64	83	h.	h.	NOUN
eurjchem-205	64	84	the	the	DET
eurjchem-205	64	85	progress	progress	NOUN
eurjchem-205	64	86	of	of	ADP
eurjchem-205	64	87	reaction	reaction	NOUN
eurjchem-205	64	88	was	be	AUX
eurjchem-205	64	89	monitored	monitor	VERB
eurjchem-205	64	90	by	by	ADP
eurjchem-205	64	91	tlc	tlc	PROPN
eurjchem-205	64	92	.	.	PUNCT
eurjchem-205	65	1	after	after	ADP
eurjchem-205	65	2	completion	completion	NOUN
eurjchem-205	65	3	of	of	ADP
eurjchem-205	65	4	reaction	reaction	NOUN
eurjchem-205	65	5	,	,	PUNCT
eurjchem-205	65	6	the	the	DET
eurjchem-205	65	7	reaction	reaction	NOUN
eurjchem-205	65	8	mixture	mixture	NOUN
eurjchem-205	65	9	was	be	AUX
eurjchem-205	65	10	quenched	quench	VERB
eurjchem-205	65	11	with	with	ADP
eurjchem-205	65	12	aqueous	aqueous	ADJ
eurjchem-205	65	13	ammonium	ammonium	NOUN
eurjchem-205	65	14	chloride	chloride	NOUN
eurjchem-205	65	15	.	.	PUNCT
eurjchem-205	66	1	the	the	DET
eurjchem-205	66	2	solvent	solvent	NOUN
eurjchem-205	66	3	was	be	AUX
eurjchem-205	66	4	evaporated	evaporate	VERB
eurjchem-205	66	5	under	under	ADP
eurjchem-205	66	6	vacuum	vacuum	NOUN
eurjchem-205	66	7	to	to	PART
eurjchem-205	66	8	get	get	VERB
eurjchem-205	66	9	residue	residue	NOUN
eurjchem-205	66	10	.	.	PUNCT
eurjchem-205	67	1	water	water	NOUN
eurjchem-205	67	2	(	(	PUNCT
eurjchem-205	67	3	10	10	NUM
eurjchem-205	67	4	ml	ml	NOUN
eurjchem-205	67	5	)	)	PUNCT
eurjchem-205	67	6	was	be	AUX
eurjchem-205	67	7	added	add	VERB
eurjchem-205	67	8	to	to	ADP
eurjchem-205	67	9	the	the	DET
eurjchem-205	67	10	residue	residue	NOUN
eurjchem-205	67	11	and	and	CCONJ
eurjchem-205	67	12	the	the	DET
eurjchem-205	67	13	product	product	NOUN
eurjchem-205	67	14	was	be	AUX
eurjchem-205	67	15	extracted	extract	VERB
eurjchem-205	67	16	using	use	VERB
eurjchem-205	67	17	ethyl	ethyl	PROPN
eurjchem-205	67	18	acetate	acetate	NOUN
eurjchem-205	67	19	(	(	PUNCT
eurjchem-205	67	20	2	2	NUM
eurjchem-205	67	21	x	x	SYM
eurjchem-205	67	22	15	15	NUM
eurjchem-205	67	23	ml	ml	NOUN
eurjchem-205	67	24	)	)	PUNCT
eurjchem-205	67	25	.	.	PUNCT
eurjchem-205	68	1	the	the	DET
eurjchem-205	68	2	combined	combine	VERB
eurjchem-205	68	3	organic	organic	ADJ
eurjchem-205	68	4	layer	layer	NOUN
eurjchem-205	68	5	was	be	AUX
eurjchem-205	68	6	dried	dry	VERB
eurjchem-205	68	7	over	over	ADP
eurjchem-205	68	8	anhydrous	anhydrous	ADJ
eurjchem-205	68	9	na2so4	na2so4	NOUN
eurjchem-205	68	10	and	and	CCONJ
eurjchem-205	68	11	evaporated	evaporate	VERB
eurjchem-205	68	12	under	under	ADP
eurjchem-205	68	13	reduced	reduce	VERB
eurjchem-205	68	14	pressure	pressure	NOUN
eurjchem-205	68	15	to	to	PART
eurjchem-205	68	16	afford	afford	VERB
eurjchem-205	68	17	a	a	DET
eurjchem-205	68	18	crude	crude	ADJ
eurjchem-205	68	19	product	product	NOUN
eurjchem-205	68	20	which	which	PRON
eurjchem-205	68	21	was	be	AUX
eurjchem-205	68	22	purified	purify	VERB
eurjchem-205	68	23	by	by	ADP
eurjchem-205	68	24	column	column	NOUN
eurjchem-205	68	25	chromatography	chromatography	NOUN
eurjchem-205	68	26	using	use	VERB
eurjchem-205	68	27	petroleum	petroleum	NOUN
eurjchem-205	68	28	ether	ether	NOUN
eurjchem-205	68	29	:	:	PUNCT
eurjchem-205	68	30	ethyl	ethyl	PROPN
eurjchem-205	68	31	acetate	acetate	PROPN
eurjchem-205	68	32	(	(	PUNCT
eurjchem-205	68	33	6.5:3.5	6.5:3.5	NUM
eurjchem-205	68	34	)	)	PUNCT
eurjchem-205	68	35	to	to	PART
eurjchem-205	68	36	afford	afford	VERB
eurjchem-205	68	37	0.130	0.130	NUM
eurjchem-205	68	38	g	g	NOUN
eurjchem-205	68	39	(	(	PUNCT
eurjchem-205	68	40	87	87	NUM
eurjchem-205	68	41	%	%	NOUN
eurjchem-205	68	42	)	)	PUNCT
eurjchem-205	68	43	of	of	ADP
eurjchem-205	68	44	the	the	DET
eurjchem-205	68	45	pure	pure	ADJ
eurjchem-205	68	46	2‐(3‐(hydroxylmethyl)quinolin‐2‐yl)quino‐	2‐(3‐(hydroxylmethyl)quinolin‐2‐yl)quino‐	NUM
eurjchem-205	68	47	zoline‐4(3h)‐one	zoline‐4(3h)‐one	NOUN
eurjchem-205	68	48	7	7	NUM
eurjchem-205	68	49	as	as	ADP
eurjchem-205	68	50	white	white	PROPN
eurjchem-205	68	51	solid	solid	PROPN
eurjchem-205	68	52	.	.	PUNCT
eurjchem-205	69	1	m.p	m.p	PROPN
eurjchem-205	69	2	.	.	PROPN
eurjchem-205	69	3	:	:	PUNCT
eurjchem-205	70	1	209‐211	209‐211	NUM
eurjchem-205	70	2	oc	oc	VERB
eurjchem-205	70	3	.	.	PROPN
eurjchem-205	71	1	ir	ir	PROPN
eurjchem-205	71	2	(	(	PUNCT
eurjchem-205	71	3	kbr	kbr	PROPN
eurjchem-205	71	4	,	,	PUNCT
eurjchem-205	71	5	max	max	PROPN
eurjchem-205	71	6	,	,	PUNCT
eurjchem-205	71	7	cm‐1	cm‐1	PROPN
eurjchem-205	71	8	):	):	PUNCT
eurjchem-205	71	9	3423	3423	NUM
eurjchem-205	71	10	,	,	PUNCT
eurjchem-205	71	11	3308	3308	NUM
eurjchem-205	71	12	,	,	PUNCT
eurjchem-205	71	13	3018	3018	NUM
eurjchem-205	71	14	,	,	PUNCT
eurjchem-205	71	15	2926	2926	NUM
eurjchem-205	71	16	,	,	PUNCT
eurjchem-205	71	17	2855	2855	NUM
eurjchem-205	71	18	,	,	PUNCT
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eurjchem-205	71	20	,	,	PUNCT
eurjchem-205	71	21	1603	1603	NUM
eurjchem-205	71	22	,	,	PUNCT
eurjchem-205	71	23	1565	1565	NUM
eurjchem-205	71	24	,	,	PUNCT
eurjchem-205	71	25	1470	1470	NUM
eurjchem-205	71	26	,	,	PUNCT
eurjchem-205	71	27	1236	1236	NUM
eurjchem-205	71	28	,	,	PUNCT
eurjchem-205	71	29	1215	1215	NUM
eurjchem-205	71	30	,	,	PUNCT
eurjchem-205	71	31	1021	1021	NUM
eurjchem-205	71	32	,	,	PUNCT
eurjchem-205	71	33	951	951	NUM
eurjchem-205	71	34	,	,	PUNCT
eurjchem-205	71	35	758	758	NUM
eurjchem-205	71	36	,	,	PUNCT
eurjchem-205	71	37	668	668	NUM
eurjchem-205	71	38	.	.	NOUN
eurjchem-205	71	39	1h	1h	NUM
eurjchem-205	71	40	nmr	nmr	NOUN
eurjchem-205	71	41	(	(	PUNCT
eurjchem-205	71	42	200	200	NUM
eurjchem-205	71	43	mhz	mhz	NOUN
eurjchem-205	71	44	,	,	PUNCT
eurjchem-205	71	45	cdcl3	cdcl3	PROPN
eurjchem-205	71	46	,	,	PUNCT
eurjchem-205	71	47	δ	δ	PROPN
eurjchem-205	71	48	,	,	PUNCT
eurjchem-205	71	49	ppm	ppm	NOUN
eurjchem-205	71	50	):	):	PUNCT
eurjchem-205	71	51	5.09	5.09	NUM
eurjchem-205	71	52	(	(	PUNCT
eurjchem-205	71	53	s	s	PROPN
eurjchem-205	71	54	,	,	PUNCT
eurjchem-205	71	55	2h	2h	NUM
eurjchem-205	71	56	,	,	PUNCT
eurjchem-205	71	57	ch2	ch2	PROPN
eurjchem-205	71	58	)	)	PUNCT
eurjchem-205	71	59	,	,	PUNCT
eurjchem-205	71	60	6.37	6.37	NUM
eurjchem-205	71	61	(	(	PUNCT
eurjchem-205	71	62	bs	bs	PROPN
eurjchem-205	71	63	,	,	PUNCT
eurjchem-205	71	64	1h	1h	NUM
eurjchem-205	71	65	,	,	PUNCT
eurjchem-205	71	66	oh	oh	INTJ
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eurjchem-205	71	68	,	,	PUNCT
eurjchem-205	71	69	7.59‐7.71	7.59‐7.71	NUM
eurjchem-205	71	70	(	(	PUNCT
eurjchem-205	71	71	m	m	PROPN
eurjchem-205	71	72	,	,	PUNCT
eurjchem-205	71	73	2h	2h	NUM
eurjchem-205	71	74	,	,	PUNCT
eurjchem-205	71	75	arh	arh	ADJ
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eurjchem-205	71	77	,	,	PUNCT
eurjchem-205	71	78	7.81‐7.92	7.81‐7.92	NUM
eurjchem-205	71	79	(	(	PUNCT
eurjchem-205	71	80	m	m	PROPN
eurjchem-205	71	81	4h	4h	NUM
eurjchem-205	71	82	,	,	PUNCT
eurjchem-205	71	83	arh	arh	PROPN
eurjchem-205	71	84	)	)	PUNCT
eurjchem-205	71	85	,	,	PUNCT
eurjchem-205	71	86	8.18‐8.20	8.18‐8.20	NUM
eurjchem-205	71	87	(	(	PUNCT
eurjchem-205	71	88	d	d	NOUN
eurjchem-205	71	89	,	,	PUNCT
eurjchem-205	71	90	j	j	PROPN
eurjchem-205	71	91	=	=	PROPN
eurjchem-205	71	92	8.36	8.36	NUM
eurjchem-205	71	93	hz	hz	NOUN
eurjchem-205	71	94	,	,	PUNCT
eurjchem-205	71	95	1h	1h	NUM
eurjchem-205	71	96	,	,	PUNCT
eurjchem-205	71	97	arh	arh	PROPN
eurjchem-205	71	98	)	)	PUNCT
eurjchem-205	71	99	,	,	PUNCT
eurjchem-205	71	100	8.31	8.31	NUM
eurjchem-205	71	101	(	(	PUNCT
eurjchem-205	71	102	s	s	PROPN
eurjchem-205	71	103	,	,	PUNCT
eurjchem-205	71	104	1h	1h	NUM
eurjchem-205	71	105	,	,	PUNCT
eurjchem-205	71	106	arh	arh	PROPN
eurjchem-205	71	107	)	)	PUNCT
eurjchem-205	71	108	,	,	PUNCT
eurjchem-205	71	109	8.40‐8.42	8.40‐8.42	NUM
eurjchem-205	71	110	(	(	PUNCT
eurjchem-205	71	111	d	d	PROPN
eurjchem-205	71	112	,	,	PUNCT
eurjchem-205	71	113	j	j	PROPN
eurjchem-205	71	114	=	=	PROPN
eurjchem-205	71	115	8.02	8.02	NUM
eurjchem-205	71	116	hz	hz	NOUN
eurjchem-205	71	117	,	,	PUNCT
eurjchem-205	71	118	1h	1h	NUM
eurjchem-205	71	119	,	,	PUNCT
eurjchem-205	71	120	arh	arh	PROPN
eurjchem-205	71	121	)	)	PUNCT
eurjchem-205	71	122	,	,	PUNCT
eurjchem-205	71	123	11.49	11.49	NUM
eurjchem-205	71	124	(	(	PUNCT
eurjchem-205	71	125	bs	bs	PROPN
eurjchem-205	71	126	,	,	PUNCT
eurjchem-205	71	127	1h	1h	NUM
eurjchem-205	71	128	,	,	PUNCT
eurjchem-205	71	129	2h	2h	NUM
eurjchem-205	71	130	)	)	PUNCT
eurjchem-205	71	131	.	.	PUNCT
eurjchem-205	72	1	13c	13c	NOUN
eurjchem-205	72	2	nmr	nmr	NOUN
eurjchem-205	72	3	(	(	PUNCT
eurjchem-205	72	4	50	50	NUM
eurjchem-205	72	5	mhz	mhz	NOUN
eurjchem-205	72	6	,	,	PUNCT
eurjchem-205	72	7			NUM
eurjchem-205	72	8	,	,	PUNCT
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eurjchem-205	72	10	):	):	PUNCT
eurjchem-205	72	11	63.9	63.9	NUM
eurjchem-205	72	12	(	(	PUNCT
eurjchem-205	72	13	ch2	ch2	PROPN
eurjchem-205	72	14	)	)	PUNCT
eurjchem-205	72	15	,	,	PUNCT
eurjchem-205	72	16	122.4	122.4	NUM
eurjchem-205	72	17	126.9	126.9	NUM
eurjchem-205	72	18	,	,	PUNCT
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eurjchem-205	72	20	,	,	PUNCT
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eurjchem-205	72	22	,	,	PUNCT
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eurjchem-205	72	24	,	,	PUNCT
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eurjchem-205	72	26	,	,	PUNCT
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eurjchem-205	72	30	130.8	130.8	NUM
eurjchem-205	72	31	,	,	PUNCT
eurjchem-205	72	32	133.9	133.9	NUM
eurjchem-205	72	33	,	,	PUNCT
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eurjchem-205	72	35	,	,	PUNCT
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eurjchem-205	72	37	,	,	PUNCT
eurjchem-205	72	38	145.8	145.8	NUM
eurjchem-205	72	39	,	,	PUNCT
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eurjchem-205	72	41	,	,	PUNCT
eurjchem-205	72	42	147.8	147.8	NUM
eurjchem-205	72	43	,	,	PUNCT
eurjchem-205	72	44	150.1	150.1	NUM
eurjchem-205	72	45	(	(	PUNCT
eurjchem-205	72	46	chmethine	chmethine	PROPN
eurjchem-205	72	47	)	)	PUNCT
eurjchem-205	72	48	,	,	PUNCT
eurjchem-205	72	49	161.0	161.0	NUM
eurjchem-205	72	50	(	(	PUNCT
eurjchem-205	72	51	c	c	NOUN
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eurjchem-205	72	53	c	c	NOUN
eurjchem-205	72	54	=	=	NOUN
eurjchem-205	72	55	o	o	NOUN
eurjchem-205	72	56	)	)	PUNCT
eurjchem-205	72	57	.	.	PUNCT
eurjchem-205	73	1	anal	anal	PROPN
eurjchem-205	73	2	.	.	PUNCT
eurjchem-205	73	3	calcd	calcd	NOUN
eurjchem-205	73	4	.	.	PUNCT
eurjchem-205	74	1	for	for	ADP
eurjchem-205	74	2	c18h13n3o2	c18h13n3o2	PROPN
eurjchem-205	74	3	(	(	PUNCT
eurjchem-205	74	4	%	%	INTJ
eurjchem-205	74	5	)	)	PUNCT
eurjchem-205	74	6	c	c	NOUN
eurjchem-205	74	7	,	,	PUNCT
eurjchem-205	74	8	71.28	71.28	NUM
eurjchem-205	74	9	;	;	PUNCT
eurjchem-205	74	10	h	h	NOUN
eurjchem-205	74	11	,	,	PUNCT
eurjchem-205	74	12	4.32	4.32	NUM
eurjchem-205	74	13	;	;	PUNCT
eurjchem-205	74	14	n	n	CCONJ
eurjchem-205	74	15	,	,	PUNCT
eurjchem-205	74	16	13.85	13.85	NUM
eurjchem-205	74	17	.	.	PUNCT
eurjchem-205	74	18	found	find	VERB
eurjchem-205	74	19	:	:	PUNCT
eurjchem-205	75	1	c	c	X
eurjchem-205	75	2	,	,	PUNCT
eurjchem-205	75	3	71.43	71.43	NUM
eurjchem-205	75	4	;	;	PUNCT
eurjchem-205	75	5	h	h	NOUN
eurjchem-205	75	6	,	,	PUNCT
eurjchem-205	75	7	4.28	4.28	NUM
eurjchem-205	75	8	;	;	PUNCT
eurjchem-205	75	9	n	n	CCONJ
eurjchem-205	75	10	,	,	PUNCT
eurjchem-205	75	11	13.68	13.68	NUM
eurjchem-205	75	12	.	.	PUNCT
eurjchem-205	76	1	2.6	2.6	NUM
eurjchem-205	76	2	.	.	PUNCT
eurjchem-205	76	3	quino[2’,3’:3,4]pyrrolo[2,1‐b]quinazolin‐11(13h)‐one	quino[2’,3’:3,4]pyrrolo[2,1‐b]quinazolin‐11(13h)‐one	NOUN
eurjchem-205	76	4	(	(	PUNCT
eurjchem-205	76	5	luotonin	luotonin	PROPN
eurjchem-205	76	6	a	a	NOUN
eurjchem-205	76	7	)	)	PUNCT
eurjchem-205	76	8	to	to	ADP
eurjchem-205	76	9	the	the	DET
eurjchem-205	76	10	solution	solution	NOUN
eurjchem-205	76	11	of	of	ADP
eurjchem-205	76	12	compound	compound	NOUN
eurjchem-205	76	13	7	7	NUM
eurjchem-205	76	14	(	(	PUNCT
eurjchem-205	76	15	100	100	NUM
eurjchem-205	76	16	mg	mg	NOUN
eurjchem-205	76	17	,	,	PUNCT
eurjchem-205	76	18	0.33	0.33	NUM
eurjchem-205	76	19	mmol	mmol	NOUN
eurjchem-205	76	20	)	)	PUNCT
eurjchem-205	76	21	and	and	CCONJ
eurjchem-205	76	22	tpp	tpp	PROPN
eurjchem-205	76	23	(	(	PUNCT
eurjchem-205	76	24	112	112	NUM
eurjchem-205	76	25	mg	mg	PROPN
eurjchem-205	76	26	,	,	PUNCT
eurjchem-205	76	27	0.43	0.43	NUM
eurjchem-205	76	28	mmol	mmol	NOUN
eurjchem-205	76	29	)	)	PUNCT
eurjchem-205	76	30	in	in	ADP
eurjchem-205	76	31	thf	thf	NOUN
eurjchem-205	76	32	(	(	PUNCT
eurjchem-205	76	33	5	5	NUM
eurjchem-205	76	34	ml	ml	NOUN
eurjchem-205	76	35	)	)	PUNCT
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eurjchem-205	76	38	solution	solution	NOUN
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eurjchem-205	76	40	dead	dead	ADJ
eurjchem-205	76	41	(	(	PUNCT
eurjchem-205	76	42	0.08	0.08	NUM
eurjchem-205	76	43	ml	ml	NOUN
eurjchem-205	76	44	,	,	PUNCT
eurjchem-205	76	45	0.39	0.39	NUM
eurjchem-205	76	46	mmol	mmol	NOUN
eurjchem-205	76	47	)	)	PUNCT
eurjchem-205	76	48	in	in	ADP
eurjchem-205	76	49	tetrahydrofuran	tetrahydrofuran	NOUN
eurjchem-205	76	50	(	(	PUNCT
eurjchem-205	76	51	thf	thf	NOUN
eurjchem-205	76	52	)	)	PUNCT
eurjchem-205	76	53	(	(	PUNCT
eurjchem-205	76	54	2	2	NUM
eurjchem-205	76	55	ml	ml	NOUN
eurjchem-205	76	56	)	)	PUNCT
eurjchem-205	76	57	dropwise	dropwise	NOUN
eurjchem-205	76	58	over	over	ADP
eurjchem-205	76	59	a	a	DET
eurjchem-205	76	60	period	period	NOUN
eurjchem-205	76	61	of	of	ADP
eurjchem-205	76	62	10	10	NUM
eurjchem-205	76	63	min	min	NOUN
eurjchem-205	76	64	at	at	ADP
eurjchem-205	76	65	room	room	NOUN
eurjchem-205	76	66	temperature	temperature	NOUN
eurjchem-205	76	67	and	and	CCONJ
eurjchem-205	76	68	further	far	ADV
eurjchem-205	76	69	stirred	stir	VERB
eurjchem-205	76	70	for	for	ADP
eurjchem-205	76	71	1	1	NUM
eurjchem-205	76	72	h.	h.	NOUN
eurjchem-205	76	73	the	the	DET
eurjchem-205	76	74	progress	progress	NOUN
eurjchem-205	76	75	of	of	ADP
eurjchem-205	76	76	the	the	DET
eurjchem-205	76	77	reaction	reaction	NOUN
eurjchem-205	76	78	was	be	AUX
eurjchem-205	76	79	monitored	monitor	VERB
eurjchem-205	76	80	by	by	ADP
eurjchem-205	76	81	tlc	tlc	PROPN
eurjchem-205	76	82	.	.	PUNCT
eurjchem-205	77	1	on	on	ADP
eurjchem-205	77	2	completion	completion	NOUN
eurjchem-205	77	3	the	the	DET
eurjchem-205	77	4	reaction	reaction	NOUN
eurjchem-205	77	5	mixture	mixture	NOUN
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eurjchem-205	77	7	concentrated	concentrate	VERB
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eurjchem-205	77	9	vacuo	vacuo	PROPN
eurjchem-205	77	10	.	.	PUNCT
eurjchem-205	78	1	the	the	DET
eurjchem-205	78	2	column	column	NOUN
eurjchem-205	78	3	chromatographic	chromatographic	ADJ
eurjchem-205	78	4	purification	purification	NOUN
eurjchem-205	78	5	of	of	ADP
eurjchem-205	78	6	the	the	DET
eurjchem-205	78	7	residue	residue	NOUN
eurjchem-205	78	8	using	use	VERB
eurjchem-205	78	9	ethyl	ethyl	PROPN
eurjchem-205	78	10	acetate	acetate	NOUN
eurjchem-205	78	11	as	as	ADP
eurjchem-205	78	12	an	an	DET
eurjchem-205	78	13	eluant	eluant	NOUN
eurjchem-205	78	14	furnished	furnish	VERB
eurjchem-205	78	15	luotonin	luotonin	ADJ
eurjchem-205	78	16	,	,	PUNCT
eurjchem-205	78	17	90	90	NUM
eurjchem-205	78	18	mg	mg	NOUN
eurjchem-205	78	19	(	(	PUNCT
eurjchem-205	78	20	95	95	NUM
eurjchem-205	78	21	%	%	NOUN
eurjchem-205	78	22	yield	yield	NOUN
eurjchem-205	78	23	)	)	PUNCT
eurjchem-205	78	24	.	.	PUNCT
eurjchem-205	79	1	m.p	m.p	PROPN
eurjchem-205	79	2	.	.	PROPN
eurjchem-205	79	3	:	:	PUNCT
eurjchem-205	80	1	284‐285	284‐285	PROPN
eurjchem-205	80	2	°	°	SYM
eurjchem-205	80	3	c	c	X
eurjchem-205	80	4	.	.	PUNCT
eurjchem-205	81	1	ir	ir	PROPN
eurjchem-205	81	2	(	(	PUNCT
eurjchem-205	81	3	kbr	kbr	PROPN
eurjchem-205	81	4	,	,	PUNCT
eurjchem-205	81	5	max	max	PROPN
eurjchem-205	81	6	,	,	PUNCT
eurjchem-205	81	7	cm‐1	cm‐1	NUM
eurjchem-205	81	8	):	):	PUNCT
eurjchem-205	81	9	1670	1670	NUM
eurjchem-205	81	10	,	,	PUNCT
eurjchem-205	81	11	1630	1630	NUM
eurjchem-205	81	12	,	,	PUNCT
eurjchem-205	81	13	1605	1605	NUM
eurjchem-205	81	14	,	,	PUNCT
eurjchem-205	81	15	1466	1466	NUM
eurjchem-205	81	16	.	.	PUNCT
eurjchem-205	82	1	1h	1h	NUM
eurjchem-205	82	2	nmr	nmr	NOUN
eurjchem-205	82	3	(	(	PUNCT
eurjchem-205	82	4	200	200	NUM
eurjchem-205	82	5	mhz	mhz	NOUN
eurjchem-205	82	6	,	,	PUNCT
eurjchem-205	82	7	cdcl3	cdcl3	PROPN
eurjchem-205	82	8	,	,	PUNCT
eurjchem-205	82	9	δ	δ	PROPN
eurjchem-205	82	10	,	,	PUNCT
eurjchem-205	82	11	ppm	ppm	NUM
eurjchem-205	82	12	):	):	PUNCT
eurjchem-205	82	13	5.34	5.34	NUM
eurjchem-205	82	14	(	(	PUNCT
eurjchem-205	82	15	s	s	NOUN
eurjchem-205	82	16	,	,	PUNCT
eurjchem-205	82	17	2h	2h	NUM
eurjchem-205	82	18	)	)	PUNCT
eurjchem-205	82	19	,	,	PUNCT
eurjchem-205	82	20	7.58	7.58	NUM
eurjchem-205	82	21	(	(	PUNCT
eurjchem-205	82	22	t	t	PROPN
eurjchem-205	82	23	,	,	PUNCT
eurjchem-205	82	24	j	j	PROPN
eurjchem-205	82	25	=	=	SYM
eurjchem-205	82	26	10	10	NUM
eurjchem-205	82	27	hz	hz	VERB
eurjchem-205	82	28	,	,	PUNCT
eurjchem-205	82	29	1h	1h	NUM
eurjchem-205	82	30	)	)	PUNCT
eurjchem-205	82	31	,	,	PUNCT
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eurjchem-205	82	34	t	t	PROPN
eurjchem-205	82	35	,	,	PUNCT
eurjchem-205	82	36	j	j	PROPN
eurjchem-205	83	1	=	=	SYM
eurjchem-205	83	2	10	10	NUM
eurjchem-205	83	3	hz	hz	VERB
eurjchem-205	83	4	,	,	PUNCT
eurjchem-205	83	5	1h	1h	NUM
eurjchem-205	83	6	)	)	PUNCT
eurjchem-205	83	7	,	,	PUNCT
eurjchem-205	83	8	7.84	7.84	NUM
eurjchem-205	83	9	(	(	PUNCT
eurjchem-205	83	10	t	t	PROPN
eurjchem-205	83	11	,	,	PUNCT
eurjchem-205	83	12	j	j	PROPN
eurjchem-205	84	1	=	=	SYM
eurjchem-205	84	2	10	10	NUM
eurjchem-205	84	3	hz	hz	VERB
eurjchem-205	84	4	,	,	PUNCT
eurjchem-205	84	5	1h	1h	NUM
eurjchem-205	84	6	)	)	PUNCT
eurjchem-205	84	7	,	,	PUNCT
eurjchem-205	84	8	7.86	7.86	NUM
eurjchem-205	84	9	(	(	PUNCT
eurjchem-205	84	10	t	t	PROPN
eurjchem-205	84	11	,	,	PUNCT
eurjchem-205	84	12	j	j	PROPN
eurjchem-205	85	1	=	=	SYM
eurjchem-205	85	2	10	10	NUM
eurjchem-205	85	3	hz	hz	VERB
eurjchem-205	85	4	,	,	PUNCT
eurjchem-205	85	5	1h	1h	NUM
eurjchem-205	85	6	)	)	PUNCT
eurjchem-205	85	7	,	,	PUNCT
eurjchem-205	85	8	7.94	7.94	NUM
eurjchem-205	85	9	(	(	PUNCT
eurjchem-205	85	10	d	d	PROPN
eurjchem-205	85	11	,	,	PUNCT
eurjchem-205	85	12	j	j	PROPN
eurjchem-205	85	13	=	=	SYM
eurjchem-205	85	14	10	10	NUM
eurjchem-205	85	15	hz	hz	VERB
eurjchem-205	85	16	,	,	PUNCT
eurjchem-205	85	17	1h	1h	NUM
eurjchem-205	85	18	)	)	PUNCT
eurjchem-205	85	19	,	,	PUNCT
eurjchem-205	85	20	8.12	8.12	NUM
eurjchem-205	85	21	(	(	PUNCT
eurjchem-205	85	22	d	d	PROPN
eurjchem-205	85	23	,	,	PUNCT
eurjchem-205	85	24	j	j	PROPN
eurjchem-205	85	25	=	=	SYM
eurjchem-205	85	26	10	10	NUM
eurjchem-205	85	27	hz	hz	VERB
eurjchem-205	85	28	,	,	PUNCT
eurjchem-205	85	29	1h	1h	NUM
eurjchem-205	85	30	)	)	PUNCT
eurjchem-205	85	31	,	,	PUNCT
eurjchem-205	85	32	8.43	8.43	NUM
eurjchem-205	85	33	(	(	PUNCT
eurjchem-205	85	34	d	d	PROPN
eurjchem-205	85	35	,	,	PUNCT
eurjchem-205	85	36	j	j	PROPN
eurjchem-205	85	37	=	=	SYM
eurjchem-205	85	38	10	10	NUM
eurjchem-205	85	39	hz	hz	VERB
eurjchem-205	85	40	,	,	PUNCT
eurjchem-205	85	41	1h	1h	NUM
eurjchem-205	85	42	)	)	PUNCT
eurjchem-205	85	43	,	,	PUNCT
eurjchem-205	85	44	8.44	8.44	NUM
eurjchem-205	85	45	(	(	PUNCT
eurjchem-205	85	46	s	s	PROPN
eurjchem-205	85	47	,	,	PUNCT
eurjchem-205	85	48	1h	1h	NUM
eurjchem-205	85	49	)	)	PUNCT
eurjchem-205	85	50	,	,	PUNCT
eurjchem-205	85	51	8.47	8.47	NUM
eurjchem-205	85	52	(	(	PUNCT
eurjchem-205	85	53	d	d	PROPN
eurjchem-205	85	54	,	,	PUNCT
eurjchem-205	85	55	j	j	PROPN
eurjchem-205	85	56	=	=	SYM
eurjchem-205	85	57	10	10	NUM
eurjchem-205	85	58	hz	hz	VERB
eurjchem-205	85	59	,	,	PUNCT
eurjchem-205	85	60	1h	1h	NUM
eurjchem-205	85	61	)	)	PUNCT
eurjchem-205	85	62	.	.	PUNCT
eurjchem-205	86	1	13c	13c	NOUN
eurjchem-205	86	2	nmr	nmr	NOUN
eurjchem-205	86	3	(	(	PUNCT
eurjchem-205	86	4	50	50	NUM
eurjchem-205	86	5	mhz	mhz	NOUN
eurjchem-205	86	6	,	,	PUNCT
eurjchem-205	86	7			NUM
eurjchem-205	86	8	,	,	PUNCT
eurjchem-205	86	9	ppm	ppm	NUM
eurjchem-205	86	10	):	):	PUNCT
eurjchem-205	86	11	47.3	47.3	NUM
eurjchem-205	86	12	(	(	PUNCT
eurjchem-205	86	13	ch2	ch2	PROPN
eurjchem-205	86	14	)	)	PUNCT
eurjchem-205	86	15	,	,	PUNCT
eurjchem-205	86	16	121.3	121.3	NUM
eurjchem-205	86	17	,	,	PUNCT
eurjchem-205	86	18	126.4	126.4	NUM
eurjchem-205	86	19	,	,	PUNCT
eurjchem-205	86	20	127.4	127.4	NUM
eurjchem-205	86	21	,	,	PUNCT
eurjchem-205	86	22	127.9	127.9	NUM
eurjchem-205	86	23	,	,	PUNCT
eurjchem-205	86	24	128.5	128.5	NUM
eurjchem-205	86	25	,	,	PUNCT
eurjchem-205	86	26	128.8	128.8	NUM
eurjchem-205	86	27	,	,	PUNCT
eurjchem-205	86	28	129.4	129.4	NUM
eurjchem-205	86	29	,	,	PUNCT
eurjchem-205	86	30	130.68	130.68	NUM
eurjchem-205	86	31	,	,	PUNCT
eurjchem-205	86	32	130.71	130.71	NUM
eurjchem-205	86	33	,	,	PUNCT
eurjchem-205	86	34	131.5	131.5	NUM
eurjchem-205	86	35	,	,	PUNCT
eurjchem-205	86	36	134.6	134.6	NUM
eurjchem-205	86	37	,	,	PUNCT
eurjchem-205	86	38	149.35	149.35	NUM
eurjchem-205	86	39	,	,	PUNCT
eurjchem-205	86	40	149.42	149.42	NUM
eurjchem-205	86	41	,	,	PUNCT
eurjchem-205	86	42	151.2	151.2	NUM
eurjchem-205	86	43	(	(	PUNCT
eurjchem-205	86	44	chmethine	chmethine	PROPN
eurjchem-205	86	45	)	)	PUNCT
eurjchem-205	86	46	,	,	PUNCT
eurjchem-205	86	47	152.5	152.5	NUM
eurjchem-205	86	48	(	(	PUNCT
eurjchem-205	86	49	c	c	NOUN
eurjchem-205	86	50	as	as	ADP
eurjchem-205	86	51	c=	c=	NOUN
eurjchem-205	86	52	o	o	NOUN
eurjchem-205	86	53	)	)	PUNCT
eurjchem-205	86	54	,	,	PUNCT
eurjchem-205	86	55	160.7	160.7	NUM
eurjchem-205	86	56	(	(	PUNCT
eurjchem-205	86	57	c	c	NOUN
eurjchem-205	86	58	as	as	ADP
eurjchem-205	86	59	c	c	NOUN
eurjchem-205	86	60	=	=	NOUN
eurjchem-205	86	61	n	n	NUM
eurjchem-205	86	62	)	)	PUNCT
eurjchem-205	86	63	.	.	PUNCT
eurjchem-205	87	1	anal	anal	PROPN
eurjchem-205	87	2	.	.	PUNCT
eurjchem-205	87	3	calcd	calcd	NOUN
eurjchem-205	87	4	.	.	PUNCT
eurjchem-205	88	1	for	for	SCONJ
eurjchem-205	88	2	c18h11n3o	c18h11n3o	PROPN
eurjchem-205	88	3	(	(	PUNCT
eurjchem-205	88	4	%	%	INTJ
eurjchem-205	88	5	):	):	PUNCT
eurjchem-205	88	6	c	c	X
eurjchem-205	88	7	,	,	PUNCT
eurjchem-205	88	8	75.78	75.78	NUM
eurjchem-205	88	9	;	;	PUNCT
eurjchem-205	88	10	h	h	NOUN
eurjchem-205	88	11	,	,	PUNCT
eurjchem-205	88	12	3.89	3.89	NUM
eurjchem-205	88	13	;	;	PUNCT
eurjchem-205	88	14	n	n	CCONJ
eurjchem-205	88	15	,	,	PUNCT
eurjchem-205	88	16	14.73	14.73	NUM
eurjchem-205	88	17	.	.	PUNCT
eurjchem-205	88	18	found	find	VERB
eurjchem-205	88	19	:	:	PUNCT
eurjchem-205	89	1	c	c	X
eurjchem-205	89	2	,	,	PUNCT
eurjchem-205	89	3	75.929	75.929	NUM
eurjchem-205	89	4	;	;	PUNCT
eurjchem-205	89	5	h	h	NOUN
eurjchem-205	89	6	,	,	PUNCT
eurjchem-205	89	7	3.96	3.96	NUM
eurjchem-205	89	8	;	;	PUNCT
eurjchem-205	89	9	n	n	CCONJ
eurjchem-205	89	10	,	,	PUNCT
eurjchem-205	89	11	14.68	14.68	NUM
eurjchem-205	89	12	.	.	PUNCT
eurjchem-205	90	1	3	3	X
eurjchem-205	90	2	.	.	NOUN
eurjchem-205	90	3	results	result	NOUN
eurjchem-205	90	4	and	and	CCONJ
eurjchem-205	90	5	discussion	discussion	VERB
eurjchem-205	90	6	the	the	DET
eurjchem-205	90	7	synthesis	synthesis	NOUN
eurjchem-205	90	8	of	of	ADP
eurjchem-205	90	9	luotonin	luotonin	ADJ
eurjchem-205	90	10	a	a	PRON
eurjchem-205	90	11	was	be	AUX
eurjchem-205	90	12	initiated	initiate	VERB
eurjchem-205	90	13	from	from	ADP
eurjchem-205	90	14	2‐	2‐	NUM
eurjchem-205	90	15	aminobenzaldehyde	aminobenzaldehyde	NOUN
eurjchem-205	90	16	1	1	NUM
eurjchem-205	90	17	(	(	PUNCT
eurjchem-205	90	18	scheme	scheme	NOUN
eurjchem-205	90	19	1	1	NUM
eurjchem-205	90	20	)	)	PUNCT
eurjchem-205	90	21	.	.	PUNCT
eurjchem-205	91	1	firstly	firstly	ADV
eurjchem-205	91	2	,	,	PUNCT
eurjchem-205	91	3	2‐aminobenzal‐	2‐aminobenzal‐	NUM
eurjchem-205	91	4	potewar	potewar	NOUN
eurjchem-205	91	5	et	et	PROPN
eurjchem-205	91	6	al	al	PROPN
eurjchem-205	91	7	.	.	PUNCT
eurjchem-205	91	8	/	/	SYM
eurjchem-205	91	9	european	european	PROPN
eurjchem-205	91	10	journal	journal	PROPN
eurjchem-205	91	11	of	of	ADP
eurjchem-205	91	12	chemistry	chemistry	NOUN
eurjchem-205	91	13	2	2	NUM
eurjchem-205	91	14	(	(	PUNCT
eurjchem-205	91	15	2	2	NUM
eurjchem-205	91	16	)	)	PUNCT
eurjchem-205	91	17	(	(	PUNCT
eurjchem-205	91	18	2011	2011	NUM
eurjchem-205	91	19	)	)	PUNCT
eurjchem-205	91	20	235‐237	235‐237	NUM
eurjchem-205	91	21	237	237	NUM
eurjchem-205	91	22	dehyde	dehyde	NOUN
eurjchem-205	91	23	was	be	AUX
eurjchem-205	91	24	condensed	condense	VERB
eurjchem-205	91	25	with	with	ADP
eurjchem-205	91	26	methyl	methyl	NOUN
eurjchem-205	91	27	acetoacetate	acetoacetate	NOUN
eurjchem-205	91	28	2	2	NUM
eurjchem-205	91	29	by	by	ADP
eurjchem-205	91	30	friedlander	friedlander	NOUN
eurjchem-205	91	31	quinoline	quinoline	NOUN
eurjchem-205	91	32	synthesis	synthesis	NOUN
eurjchem-205	91	33	using	use	VERB
eurjchem-205	91	34	il	il	PROPN
eurjchem-205	91	35	,	,	PUNCT
eurjchem-205	91	36	1‐n‐butylimidazolium	1‐n‐butylimidazolium	NUM
eurjchem-205	91	37	tetrafluoroborate	tetrafluoroborate	NOUN
eurjchem-205	91	38	(	(	PUNCT
eurjchem-205	91	39	[	[	X
eurjchem-205	91	40	hbim]bf4	hbim]bf4	X
eurjchem-205	91	41	)	)	PUNCT
eurjchem-205	91	42	as	as	ADP
eurjchem-205	91	43	reaction	reaction	NOUN
eurjchem-205	91	44	medium	medium	NOUN
eurjchem-205	91	45	as	as	ADV
eurjchem-205	91	46	well	well	ADV
eurjchem-205	91	47	as	as	ADP
eurjchem-205	91	48	promoter	promoter	NOUN
eurjchem-205	91	49	to	to	PART
eurjchem-205	91	50	afford	afford	VERB
eurjchem-205	91	51	2‐methyl	2‐methyl	PROPN
eurjchem-205	91	52	quinoline‐3‐carboxylic	quinoline‐3‐carboxylic	PROPN
eurjchem-205	91	53	acid	acid	NOUN
eurjchem-205	91	54	methyl	methyl	NOUN
eurjchem-205	91	55	ester	ester	NOUN
eurjchem-205	91	56	in	in	ADP
eurjchem-205	91	57	73	73	NUM
eurjchem-205	91	58	%	%	NOUN
eurjchem-205	91	59	yield	yield	NOUN
eurjchem-205	91	60	in	in	ADP
eurjchem-205	91	61	the	the	DET
eurjchem-205	91	62	absence	absence	NOUN
eurjchem-205	91	63	of	of	ADP
eurjchem-205	91	64	any	any	DET
eurjchem-205	91	65	additional	additional	ADJ
eurjchem-205	91	66	catalyst	catalyst	NOUN
eurjchem-205	91	67	as	as	SCONJ
eurjchem-205	91	68	described	describe	VERB
eurjchem-205	91	69	in	in	ADP
eurjchem-205	91	70	our	our	PRON
eurjchem-205	91	71	previous	previous	ADJ
eurjchem-205	91	72	report	report	NOUN
eurjchem-205	91	73	[	[	X
eurjchem-205	91	74	39	39	NUM
eurjchem-205	91	75	]	]	PUNCT
eurjchem-205	91	76	.	.	PUNCT
eurjchem-205	92	1	scheme	scheme	NOUN
eurjchem-205	92	2	1	1	NUM
eurjchem-205	92	3	the	the	DET
eurjchem-205	92	4	bronsted	bronste	VERB
eurjchem-205	92	5	acidic	acidic	PROPN
eurjchem-205	92	6	il	il	PROPN
eurjchem-205	92	7	was	be	AUX
eurjchem-205	92	8	responsible	responsible	ADJ
eurjchem-205	92	9	for	for	ADP
eurjchem-205	92	10	promoting	promote	VERB
eurjchem-205	92	11	the	the	DET
eurjchem-205	92	12	reaction	reaction	NOUN
eurjchem-205	92	13	.	.	PUNCT
eurjchem-205	93	1	the	the	DET
eurjchem-205	93	2	1h	1h	NUM
eurjchem-205	93	3	nmr	nmr	NOUN
eurjchem-205	93	4	spectrum	spectrum	NOUN
eurjchem-205	93	5	of	of	ADP
eurjchem-205	93	6	3	3	NUM
eurjchem-205	93	7	shows	show	NOUN
eurjchem-205	93	8	peak	peak	NOUN
eurjchem-205	93	9	at	at	ADP
eurjchem-205	93	10	3.01	3.01	NUM
eurjchem-205	93	11	ppm	ppm	NOUN
eurjchem-205	93	12	as	as	ADP
eurjchem-205	93	13	singlet	singlet	NOUN
eurjchem-205	93	14	corresponding	correspond	VERB
eurjchem-205	93	15	to	to	ADP
eurjchem-205	93	16	the	the	DET
eurjchem-205	93	17	methyl	methyl	NOUN
eurjchem-205	93	18	at	at	ADP
eurjchem-205	93	19	c‐2	c‐2	NOUN
eurjchem-205	93	20	and	and	CCONJ
eurjchem-205	93	21	peak	peak	NOUN
eurjchem-205	93	22	at	at	ADP
eurjchem-205	93	23	3.99	3.99	NUM
eurjchem-205	93	24	ppm	ppm	NOUN
eurjchem-205	93	25	as	as	ADP
eurjchem-205	93	26	singlet	singlet	NOUN
eurjchem-205	93	27	corresponding	correspond	VERB
eurjchem-205	93	28	to	to	ADP
eurjchem-205	93	29	the	the	DET
eurjchem-205	93	30	methyl	methyl	NOUN
eurjchem-205	93	31	of	of	ADP
eurjchem-205	93	32	methylcarboxylate	methylcarboxylate	ADJ
eurjchem-205	93	33	supporting	support	VERB
eurjchem-205	93	34	its	its	PRON
eurjchem-205	93	35	formation	formation	NOUN
eurjchem-205	93	36	.	.	PUNCT
eurjchem-205	94	1	the	the	DET
eurjchem-205	94	2	product	product	NOUN
eurjchem-205	94	3	3	3	NUM
eurjchem-205	94	4	was	be	AUX
eurjchem-205	94	5	then	then	ADV
eurjchem-205	94	6	oxidized	oxidize	VERB
eurjchem-205	94	7	using	use	VERB
eurjchem-205	94	8	selenium	selenium	NOUN
eurjchem-205	94	9	dioxide	dioxide	NOUN
eurjchem-205	94	10	in	in	ADP
eurjchem-205	94	11	xylene	xylene	NOUN
eurjchem-205	94	12	to	to	PART
eurjchem-205	94	13	afford	afford	VERB
eurjchem-205	94	14	2‐formylquinoline‐3‐carboxylic	2‐formylquinoline‐3‐carboxylic	NUM
eurjchem-205	94	15	acid	acid	NOUN
eurjchem-205	94	16	methyl	methyl	NOUN
eurjchem-205	94	17	ester	ester	NOUN
eurjchem-205	94	18	4	4	NUM
eurjchem-205	94	19	in	in	ADP
eurjchem-205	94	20	69	69	NUM
eurjchem-205	94	21	%	%	NOUN
eurjchem-205	94	22	yields	yield	NOUN
eurjchem-205	94	23	.	.	PUNCT
eurjchem-205	95	1	the	the	DET
eurjchem-205	95	2	formation	formation	NOUN
eurjchem-205	95	3	of	of	ADP
eurjchem-205	95	4	compound	compound	NOUN
eurjchem-205	95	5	4	4	NUM
eurjchem-205	95	6	was	be	AUX
eurjchem-205	95	7	confirmed	confirm	VERB
eurjchem-205	95	8	by	by	ADP
eurjchem-205	95	9	1h	1h	NUM
eurjchem-205	95	10	nmr	nmr	NOUN
eurjchem-205	95	11	showing	show	VERB
eurjchem-205	95	12	the	the	DET
eurjchem-205	95	13	peak	peak	NOUN
eurjchem-205	95	14	at	at	ADP
eurjchem-205	95	15	10.4	10.4	NUM
eurjchem-205	95	16	ppm	ppm	NOUN
eurjchem-205	95	17	for	for	ADP
eurjchem-205	95	18	the	the	DET
eurjchem-205	95	19	hydrogen	hydrogen	NOUN
eurjchem-205	95	20	of	of	ADP
eurjchem-205	95	21	aldehyde	aldehyde	NOUN
eurjchem-205	95	22	and	and	CCONJ
eurjchem-205	95	23	the	the	DET
eurjchem-205	95	24	disappearance	disappearance	NOUN
eurjchem-205	95	25	of	of	ADP
eurjchem-205	95	26	peak	peak	NOUN
eurjchem-205	95	27	at	at	ADP
eurjchem-205	95	28	3.01	3.01	NUM
eurjchem-205	95	29	ppm	ppm	NOUN
eurjchem-205	95	30	corresponding	correspond	VERB
eurjchem-205	95	31	to	to	ADP
eurjchem-205	95	32	the	the	DET
eurjchem-205	95	33	methyl	methyl	NOUN
eurjchem-205	95	34	at	at	ADP
eurjchem-205	95	35	c‐2	c‐2	NOUN
eurjchem-205	95	36	.	.	PUNCT
eurjchem-205	96	1	the	the	DET
eurjchem-205	96	2	compound	compound	NOUN
eurjchem-205	96	3	4	4	NUM
eurjchem-205	96	4	was	be	AUX
eurjchem-205	96	5	then	then	ADV
eurjchem-205	96	6	condensed	condense	VERB
eurjchem-205	96	7	with	with	ADP
eurjchem-205	96	8	anthranilamide	anthranilamide	ADV
eurjchem-205	96	9	5	5	NUM
eurjchem-205	96	10	using	use	VERB
eurjchem-205	96	11	ferric	ferric	ADJ
eurjchem-205	96	12	chloride	chloride	NOUN
eurjchem-205	96	13	(	(	PUNCT
eurjchem-205	96	14	fecl3.6h2o	fecl3.6h2o	NOUN
eurjchem-205	96	15	)	)	PUNCT
eurjchem-205	96	16	in	in	ADP
eurjchem-205	96	17	water	water	NOUN
eurjchem-205	96	18	to	to	PART
eurjchem-205	96	19	afford	afford	VERB
eurjchem-205	96	20	6	6	NUM
eurjchem-205	96	21	via	via	ADP
eurjchem-205	96	22	schiff	schiff	NOUN
eurjchem-205	96	23	base	base	NOUN
eurjchem-205	96	24	formation	formation	NOUN
eurjchem-205	96	25	and	and	CCONJ
eurjchem-205	96	26	spontaneous	spontaneous	ADJ
eurjchem-205	96	27	cyclization	cyclization	NOUN
eurjchem-205	96	28	the	the	DET
eurjchem-205	96	29	yield	yield	NOUN
eurjchem-205	96	30	was	be	AUX
eurjchem-205	96	31	76	76	NUM
eurjchem-205	96	32	%	%	NOUN
eurjchem-205	96	33	.	.	PUNCT
eurjchem-205	97	1	the	the	DET
eurjchem-205	97	2	13c	13c	NUM
eurjchem-205	97	3	nmr	nmr	NOUN
eurjchem-205	97	4	of	of	ADP
eurjchem-205	97	5	compound	compound	NOUN
eurjchem-205	97	6	showed	show	VERB
eurjchem-205	97	7	peaks	peak	NOUN
eurjchem-205	97	8	at	at	ADP
eurjchem-205	97	9	52.8	52.8	NUM
eurjchem-205	97	10	(	(	PUNCT
eurjchem-205	97	11	carbon	carbon	NOUN
eurjchem-205	97	12	of	of	ADP
eurjchem-205	97	13	methyl	methyl	NOUN
eurjchem-205	97	14	ester	ester	NOUN
eurjchem-205	97	15	)	)	PUNCT
eurjchem-205	97	16	,	,	PUNCT
eurjchem-205	97	17	161.2	161.2	NUM
eurjchem-205	97	18	(	(	PUNCT
eurjchem-205	97	19	carbonyl	carbonyl	NOUN
eurjchem-205	97	20	carbon	carbon	NOUN
eurjchem-205	97	21	of	of	ADP
eurjchem-205	97	22	amide	amide	NOUN
eurjchem-205	97	23	)	)	PUNCT
eurjchem-205	97	24	,	,	PUNCT
eurjchem-205	97	25	168.8	168.8	NUM
eurjchem-205	97	26	(	(	PUNCT
eurjchem-205	97	27	carbonyl	carbonyl	NOUN
eurjchem-205	97	28	carbon	carbon	NOUN
eurjchem-205	97	29	of	of	ADP
eurjchem-205	97	30	ester	ester	NOUN
eurjchem-205	97	31	)	)	PUNCT
eurjchem-205	97	32	,	,	PUNCT
eurjchem-205	97	33	and	and	CCONJ
eurjchem-205	97	34	148.3	148.3	NUM
eurjchem-205	97	35	(	(	PUNCT
eurjchem-205	97	36	c‐2	c‐2	NOUN
eurjchem-205	97	37	of	of	ADP
eurjchem-205	97	38	quinazolinone	quinazolinone	NUM
eurjchem-205	97	39	)	)	PUNCT
eurjchem-205	97	40	confirming	confirm	VERB
eurjchem-205	97	41	its	its	PRON
eurjchem-205	97	42	formation	formation	NOUN
eurjchem-205	97	43	.	.	PUNCT
eurjchem-205	98	1	an	an	DET
eurjchem-205	98	2	important	important	ADJ
eurjchem-205	98	3	point	point	NOUN
eurjchem-205	98	4	to	to	PART
eurjchem-205	98	5	note	note	VERB
eurjchem-205	98	6	is	be	AUX
eurjchem-205	98	7	that	that	PRON
eurjchem-205	98	8	is	be	AUX
eurjchem-205	98	9	water	water	NOUN
eurjchem-205	98	10	has	have	AUX
eurjchem-205	98	11	been	be	AUX
eurjchem-205	98	12	employed	employ	VERB
eurjchem-205	98	13	as	as	ADP
eurjchem-205	98	14	a	a	DET
eurjchem-205	98	15	green	green	ADJ
eurjchem-205	98	16	solvent	solvent	NOUN
eurjchem-205	98	17	which	which	PRON
eurjchem-205	98	18	is	be	AUX
eurjchem-205	98	19	cheap	cheap	ADJ
eurjchem-205	98	20	and	and	CCONJ
eurjchem-205	98	21	abundantly	abundantly	ADV
eurjchem-205	98	22	available	available	ADJ
eurjchem-205	98	23	.	.	PUNCT
eurjchem-205	99	1	compound	compound	NOUN
eurjchem-205	99	2	6	6	NUM
eurjchem-205	99	3	was	be	AUX
eurjchem-205	99	4	then	then	ADV
eurjchem-205	99	5	reduced	reduce	VERB
eurjchem-205	99	6	by	by	ADP
eurjchem-205	99	7	using	use	VERB
eurjchem-205	99	8	sodium	sodium	NOUN
eurjchem-205	99	9	borohydride‐calcium	borohydride‐calcium	NOUN
eurjchem-205	99	10	chloride	chloride	NOUN
eurjchem-205	99	11	in	in	ADP
eurjchem-205	99	12	ethanol	ethanol	NOUN
eurjchem-205	99	13	to	to	PART
eurjchem-205	99	14	furnish	furnish	VERB
eurjchem-205	99	15	2‐(‐	2‐(‐	PROPN
eurjchem-205	99	16	quinoline‐3‐hydroxymethyl)‐4(3h)‐quinazoline	quinoline‐3‐hydroxymethyl)‐4(3h)‐quinazoline	PROPN
eurjchem-205	99	17	7	7	NUM
eurjchem-205	99	18	in	in	ADP
eurjchem-205	99	19	87	87	NUM
eurjchem-205	99	20	%	%	NOUN
eurjchem-205	99	21	.	.	PUNCT
eurjchem-205	100	1	this	this	DET
eurjchem-205	100	2	compound	compound	NOUN
eurjchem-205	100	3	has	have	AUX
eurjchem-205	100	4	been	be	AUX
eurjchem-205	100	5	converted	convert	VERB
eurjchem-205	100	6	to	to	ADP
eurjchem-205	100	7	luotonin	luotonin	PROPN
eurjchem-205	100	8	a	a	PRON
eurjchem-205	100	9	in	in	ADP
eurjchem-205	100	10	the	the	DET
eurjchem-205	100	11	literature	literature	NOUN
eurjchem-205	100	12	in	in	ADP
eurjchem-205	100	13	one	one	NUM
eurjchem-205	100	14	step	step	NOUN
eurjchem-205	100	15	by	by	ADP
eurjchem-205	100	16	using	use	VERB
eurjchem-205	100	17	standard	standard	ADJ
eurjchem-205	100	18	mitsunobu	mitsunobu	NOUN
eurjchem-205	100	19	reaction	reaction	NOUN
eurjchem-205	100	20	conditions	condition	NOUN
eurjchem-205	100	21	using	use	VERB
eurjchem-205	100	22	triphenylphosphine	triphenylphosphine	NOUN
eurjchem-205	100	23	,	,	PUNCT
eurjchem-205	100	24	diethyl	diethyl	NOUN
eurjchem-205	100	25	azodicarboxylate	azodicarboxylate	NOUN
eurjchem-205	100	26	in	in	ADP
eurjchem-205	100	27	tetrahydrofuran	tetrahydrofuran	NOUN
eurjchem-205	100	28	by	by	ADP
eurjchem-205	100	29	a	a	DET
eurjchem-205	100	30	simple	simple	ADJ
eurjchem-205	100	31	procedure	procedure	NOUN
eurjchem-205	100	32	[	[	X
eurjchem-205	100	33	27	27	NUM
eurjchem-205	100	34	]	]	PUNCT
eurjchem-205	100	35	.	.	PUNCT
eurjchem-205	101	1	we	we	PRON
eurjchem-205	101	2	followed	follow	VERB
eurjchem-205	101	3	the	the	DET
eurjchem-205	101	4	method	method	NOUN
eurjchem-205	101	5	published	publish	VERB
eurjchem-205	101	6	in	in	ADP
eurjchem-205	101	7	literature	literature	NOUN
eurjchem-205	101	8	to	to	PART
eurjchem-205	101	9	complete	complete	VERB
eurjchem-205	101	10	the	the	DET
eurjchem-205	101	11	synthesis	synthesis	NOUN
eurjchem-205	101	12	of	of	ADP
eurjchem-205	101	13	luotonin	luotonin	NOUN
eurjchem-205	101	14	a	a	DET
eurjchem-205	101	15	the	the	DET
eurjchem-205	101	16	spectral	spectral	ADJ
eurjchem-205	101	17	data	datum	NOUN
eurjchem-205	101	18	and	and	CCONJ
eurjchem-205	101	19	melting	melting	NOUN
eurjchem-205	101	20	point	point	NOUN
eurjchem-205	101	21	of	of	ADP
eurjchem-205	101	22	luotonin	luotonin	ADV
eurjchem-205	101	23	a	a	DET
eurjchem-205	101	24	exactly	exactly	ADV
eurjchem-205	101	25	matched	match	VERB
eurjchem-205	101	26	the	the	DET
eurjchem-205	101	27	standard	standard	ADJ
eurjchem-205	101	28	compound	compound	NOUN
eurjchem-205	101	29	.	.	PUNCT
eurjchem-205	102	1	in	in	ADP
eurjchem-205	102	2	conclusion	conclusion	NOUN
eurjchem-205	102	3	,	,	PUNCT
eurjchem-205	102	4	the	the	DET
eurjchem-205	102	5	formal	formal	ADJ
eurjchem-205	102	6	synthesis	synthesis	NOUN
eurjchem-205	102	7	of	of	ADP
eurjchem-205	102	8	luotonin	luotonin	ADJ
eurjchem-205	102	9	a	a	PRON
eurjchem-205	102	10	was	be	AUX
eurjchem-205	102	11	achieved	achieve	VERB
eurjchem-205	102	12	in	in	ADP
eurjchem-205	102	13	five	five	NUM
eurjchem-205	102	14	steps	step	NOUN
eurjchem-205	102	15	;	;	PUNCT
eurjchem-205	102	16	the	the	DET
eurjchem-205	102	17	green	green	ADJ
eurjchem-205	102	18	solvents	solvent	NOUN
eurjchem-205	102	19	ionic	ionic	ADJ
eurjchem-205	102	20	liquid	liquid	NOUN
eurjchem-205	102	21	and	and	CCONJ
eurjchem-205	102	22	water	water	NOUN
eurjchem-205	102	23	were	be	AUX
eurjchem-205	102	24	used	use	VERB
eurjchem-205	102	25	step	step	NOUN
eurjchem-205	102	26	1	1	NUM
eurjchem-205	102	27	and	and	CCONJ
eurjchem-205	102	28	3	3	NUM
eurjchem-205	102	29	which	which	PRON
eurjchem-205	102	30	have	have	AUX
eurjchem-205	102	31	resulted	result	VERB
eurjchem-205	102	32	in	in	ADP
eurjchem-205	102	33	shortened	shorten	VERB
eurjchem-205	102	34	reaction	reaction	NOUN
eurjchem-205	102	35	times	time	NOUN
eurjchem-205	102	36	.	.	PUNCT
eurjchem-205	103	1	the	the	DET
eurjchem-205	103	2	overall	overall	ADJ
eurjchem-205	103	3	yield	yield	NOUN
eurjchem-205	103	4	is	be	AUX
eurjchem-205	103	5	better	well	ADJ
eurjchem-205	103	6	than	than	ADP
eurjchem-205	103	7	those	those	PRON
eurjchem-205	103	8	reported	report	VERB
eurjchem-205	103	9	so	so	ADV
eurjchem-205	103	10	far	far	ADV
eurjchem-205	103	11	.	.	PUNCT
eurjchem-205	104	1	also	also	ADV
eurjchem-205	104	2	the	the	DET
eurjchem-205	104	3	synthesis	synthesis	NOUN
eurjchem-205	104	4	of	of	ADP
eurjchem-205	104	5	luotonin	luotonin	ADJ
eurjchem-205	104	6	a	a	PRON
eurjchem-205	104	7	in	in	ADP
eurjchem-205	104	8	our	our	PRON
eurjchem-205	104	9	laboratory	laboratory	NOUN
eurjchem-205	104	10	was	be	AUX
eurjchem-205	104	11	achieved	achieve	VERB
eurjchem-205	104	12	at	at	ADP
eurjchem-205	104	13	easily	easily	ADV
eurjchem-205	104	14	accessible	accessible	ADJ
eurjchem-205	104	15	reaction	reaction	NOUN
eurjchem-205	104	16	temperatures	temperature	NOUN
eurjchem-205	104	17	.	.	PUNCT
eurjchem-205	105	1	the	the	DET
eurjchem-205	105	2	process	process	NOUN
eurjchem-205	105	3	is	be	AUX
eurjchem-205	105	4	amenable	amenable	ADJ
eurjchem-205	105	5	to	to	PART
eurjchem-205	105	6	scale	scale	VERB
eurjchem-205	105	7	up	up	ADP
eurjchem-205	105	8	and	and	CCONJ
eurjchem-205	105	9	can	can	AUX
eurjchem-205	105	10	be	be	AUX
eurjchem-205	105	11	gainfully	gainfully	ADV
eurjchem-205	105	12	employed	employ	VERB
eurjchem-205	105	13	to	to	PART
eurjchem-205	105	14	synthesize	synthesize	VERB
eurjchem-205	105	15	a	a	DET
eurjchem-205	105	16	library	library	NOUN
eurjchem-205	105	17	of	of	ADP
eurjchem-205	105	18	luotonin	luotonin	ADJ
eurjchem-205	105	19	analogues	analogue	NOUN
eurjchem-205	105	20	.	.	PUNCT
eurjchem-205	106	1	acknowledgement	acknowledgement	NOUN
eurjchem-205	106	2	we	we	PRON
eurjchem-205	106	3	are	be	AUX
eurjchem-205	106	4	grateful	grateful	ADJ
eurjchem-205	106	5	to	to	ADP
eurjchem-205	106	6	the	the	DET
eurjchem-205	106	7	director	director	NOUN
eurjchem-205	106	8	,	,	PUNCT
eurjchem-205	106	9	national	national	PROPN
eurjchem-205	106	10	chemical	chemical	PROPN
eurjchem-205	106	11	laboratory	laboratory	NOUN
eurjchem-205	106	12	for	for	ADP
eurjchem-205	106	13	providing	provide	VERB
eurjchem-205	106	14	with	with	ADP
eurjchem-205	106	15	the	the	DET
eurjchem-205	106	16	necessary	necessary	ADJ
eurjchem-205	106	17	support	support	NOUN
eurjchem-205	106	18	and	and	CCONJ
eurjchem-205	106	19	infrastructure	infrastructure	NOUN
eurjchem-205	106	20	for	for	ADP
eurjchem-205	106	21	carrying	carry	VERB
eurjchem-205	106	22	out	out	ADP
eurjchem-205	106	23	this	this	DET
eurjchem-205	106	24	work	work	NOUN
eurjchem-205	106	25	.	.	PUNCT
eurjchem-205	107	1	references	reference	NOUN
eurjchem-205	107	2	[	[	X
eurjchem-205	107	3	1	1	NUM
eurjchem-205	107	4	]	]	PUNCT
eurjchem-205	107	5	.	.	PUNCT
eurjchem-205	108	1	hesse	hesse	PROPN
eurjchem-205	108	2	,	,	PUNCT
eurjchem-205	108	3	m.	m.	NOUN
eurjchem-205	108	4	in	in	ADP
eurjchem-205	108	5	alkaloids	alkaloid	NOUN
eurjchem-205	108	6	,	,	PUNCT
eurjchem-205	108	7	wiley‐vch	wiley‐vch	PROPN
eurjchem-205	108	8	,	,	PUNCT
eurjchem-205	108	9	weinheim	weinheim	PROPN
eurjchem-205	108	10	,	,	PUNCT
eurjchem-205	108	11	2002	2002	NUM
eurjchem-205	108	12	,	,	PUNCT
eurjchem-205	108	13	pp	pp	ADJ
eurjchem-205	108	14	.	.	PUNCT
eurjchem-205	109	1	59	59	NUM
eurjchem-205	109	2	.	.	PUNCT
eurjchem-205	110	1	[	[	X
eurjchem-205	110	2	2	2	NUM
eurjchem-205	110	3	]	]	PUNCT
eurjchem-205	110	4	.	.	PUNCT
eurjchem-205	111	1	jayapaul	jayapaul	PROPN
eurjchem-205	111	2	,	,	PUNCT
eurjchem-205	111	3	k.	k.	PROPN
eurjchem-205	111	4	;	;	PUNCT
eurjchem-205	111	5	kavi	kavi	PROPN
eurjchem-205	111	6	,	,	PUNCT
eurjchem-205	111	7	k.	k.	PROPN
eurjchem-205	112	1	p.	p.	PROPN
eurjchem-205	112	2	b.	b.	PROPN
eurjchem-205	113	1	;	;	PUNCT
eurjchem-205	113	2	janardhan	janardhan	PROPN
eurjchem-205	113	3	,	,	PUNCT
eurjchem-205	113	4	r.	r.	PROPN
eurjchem-205	113	5	k.	k.	PROPN
eurjchem-205	114	1	in	in	ADP
eurjchem-205	114	2	vitro	vitro	X
eurjchem-205	114	3	cell	cell	NOUN
eurjchem-205	114	4	dev	dev	NOUN
eurjchem-205	114	5	boil	boil	NOUN
eurjchem-205	114	6	plant	plant	NOUN
eurjchem-205	114	7	.	.	PUNCT
eurjchem-205	115	1	2005	2005	NUM
eurjchem-205	115	2	,	,	PUNCT
eurjchem-205	115	3	41	41	NUM
eurjchem-205	115	4	,	,	PUNCT
eurjchem-205	115	5	682‐685	682‐685	NUM
eurjchem-205	115	6	.	.	PUNCT
eurjchem-205	116	1	[	[	X
eurjchem-205	116	2	3	3	NUM
eurjchem-205	116	3	]	]	PUNCT
eurjchem-205	116	4	.	.	PUNCT
eurjchem-205	117	1	xie	xie	PROPN
eurjchem-205	117	2	,	,	PUNCT
eurjchem-205	117	3	l.	l.	PROPN
eurjchem-205	117	4	h.	h.	PROPN
eurjchem-205	117	5	;	;	PUNCT
eurjchem-205	117	6	lin	lin	PROPN
eurjchem-205	117	7	,	,	PUNCT
eurjchem-205	117	8	j.	j.	PROPN
eurjchem-205	117	9	a.	a.	PROPN
eurjchem-205	117	10	;	;	PUNCT
eurjchem-205	117	11	smith	smith	PROPN
eurjchem-205	117	12	,	,	PUNCT
eurjchem-205	117	13	k.	k.	PROPN
eurjchem-205	117	14	;	;	PUNCT
eurjchem-205	117	15	zhang	zhang	PROPN
eurjchem-205	117	16	,	,	PUNCT
eurjchem-205	117	17	j.	j.	PROPN
eurjchem-205	117	18	;	;	PUNCT
eurjchem-205	117	19	skillman	skillman	PROPN
eurjchem-205	117	20	,	,	PUNCT
eurjchem-205	117	21	d.	d.	PROPN
eurjchem-205	117	22	s.	s.	PROPN
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eurjchem-205	117	24	.	.	PUNCT
eurjchem-205	118	1	agents	agents	PROPN
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eurjchem-205	118	3	.	.	PUNCT
eurjchem-205	119	1	2006	2006	NUM
eurjchem-205	119	2	,	,	PUNCT
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eurjchem-205	119	4	,	,	PUNCT
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eurjchem-205	119	6	.	.	PUNCT
eurjchem-205	120	1	[	[	X
eurjchem-205	120	2	4	4	NUM
eurjchem-205	120	3	]	]	PUNCT
eurjchem-205	120	4	.	.	PUNCT
eurjchem-205	121	1	guan	guan	PROPN
eurjchem-205	121	2	,	,	PUNCT
eurjchem-205	121	3	j.	j.	PROPN
eurjchem-205	121	4	;	;	PUNCT
eurjchem-205	121	5	zhang	zhang	PROPN
eurjchem-205	121	6	,	,	PUNCT
eurjchem-205	121	7	q.	q.	PROPN
eurjchem-205	121	8	;	;	PUNCT
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eurjchem-205	121	15	n.	n.	NOUN
eurjchem-205	121	16	;	;	PUNCT
eurjchem-205	121	17	ager	ager	X
eurjchem-205	121	18	,	,	PUNCT
eurjchem-205	121	19	a.	a.	NOUN
eurjchem-205	121	20	;	;	PUNCT
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eurjchem-205	121	22	,	,	PUNCT
eurjchem-205	121	23	l.	l.	PROPN
eurjchem-205	121	24	;	;	PUNCT
eurjchem-205	121	25	lin	lin	PROPN
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eurjchem-205	121	28	a.	a.	PROPN
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eurjchem-205	121	30	.	.	PUNCT
eurjchem-205	122	1	agents	agents	PROPN
eurjchem-205	122	2	chemother	chemother	PROPN
eurjchem-205	122	3	.	.	PUNCT
eurjchem-205	123	1	2005	2005	NUM
eurjchem-205	123	2	,	,	PUNCT
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eurjchem-205	123	4	,	,	PUNCT
eurjchem-205	123	5	4928‐4933	4928‐4933	NUM
eurjchem-205	123	6	.	.	PUNCT
eurjchem-205	124	1	[	[	X
eurjchem-205	124	2	5	5	NUM
eurjchem-205	124	3	]	]	X
eurjchem-205	124	4	.	.	PUNCT
eurjchem-205	125	1	mhaske	mhaske	PROPN
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eurjchem-205	125	3	s.	s.	PROPN
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eurjchem-205	126	1	[	[	X
eurjchem-205	126	2	6	6	NUM
eurjchem-205	126	3	]	]	PUNCT
eurjchem-205	126	4	.	.	PUNCT
eurjchem-205	127	1	ma	ma	PROPN
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eurjchem-205	127	3	z.	z.	PROPN
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eurjchem-205	127	6	,	,	PUNCT
eurjchem-205	127	7	y.	y.	PROPN
eurjchem-205	127	8	;	;	PUNCT
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eurjchem-205	127	10	,	,	PUNCT
eurjchem-205	127	11	t.	t.	PROPN
eurjchem-205	127	12	;	;	PUNCT
eurjchem-205	127	13	chen	chen	PROPN
eurjchem-205	127	14	,	,	PUNCT
eurjchem-205	127	15	y.	y.	PROPN
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eurjchem-205	127	18	,	,	PUNCT
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eurjchem-205	127	22	.	.	PUNCT
eurjchem-205	128	1	[	[	X
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eurjchem-205	128	3	]	]	PUNCT
eurjchem-205	128	4	.	.	PUNCT
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eurjchem-205	129	8	n.	n.	PROPN
eurjchem-205	129	9	j.	j.	PROPN
eurjchem-205	129	10	;	;	PUNCT
eurjchem-205	129	11	hecht	hecht	PROPN
eurjchem-205	129	12	,	,	PUNCT
eurjchem-205	129	13	s.	s.	PROPN
eurjchem-205	129	14	m.	m.	PROPN
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eurjchem-205	129	16	.	.	PUNCT
eurjchem-205	130	1	med	med	PROPN
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eurjchem-205	131	4	,	,	PUNCT
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eurjchem-205	131	6	.	.	PUNCT
eurjchem-205	132	1	[	[	X
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eurjchem-205	132	3	]	]	PUNCT
eurjchem-205	132	4	.	.	PUNCT
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eurjchem-205	133	6	,	,	PUNCT
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eurjchem-205	133	8	,	,	PUNCT
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eurjchem-205	134	3	]	]	PUNCT
eurjchem-205	134	4	.	.	PUNCT
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eurjchem-205	134	18	,	,	PUNCT
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eurjchem-205	135	3	]	]	PUNCT
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eurjchem-205	137	3	]	]	PUNCT
eurjchem-205	137	4	.	.	PUNCT
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eurjchem-205	139	2	,	,	PUNCT
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eurjchem-205	139	4	,	,	PUNCT
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eurjchem-205	140	3	]	]	PUNCT
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eurjchem-205	142	3	]	]	PUNCT
eurjchem-205	142	4	.	.	PUNCT
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eurjchem-205	143	2	,	,	PUNCT
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eurjchem-205	143	14	,	,	PUNCT
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eurjchem-205	143	18	,	,	PUNCT
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eurjchem-205	143	25	.	.	PUNCT
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eurjchem-205	144	2	.	.	PUNCT
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eurjchem-205	145	2	.	.	PUNCT
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eurjchem-205	146	2	,	,	PUNCT
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eurjchem-205	146	4	,	,	PUNCT
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eurjchem-205	147	3	]	]	PUNCT
eurjchem-205	147	4	.	.	PUNCT
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eurjchem-205	149	3	]	]	PUNCT
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eurjchem-205	149	16	,	,	PUNCT
eurjchem-205	149	17	k.	k.	PROPN
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eurjchem-205	150	7	.	.	PUNCT
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eurjchem-205	151	2	,	,	PUNCT
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eurjchem-205	155	2	,	,	PUNCT
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eurjchem-205	155	4	,	,	PUNCT
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eurjchem-205	155	6	.	.	PUNCT
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eurjchem-205	156	3	]	]	PUNCT
eurjchem-205	156	4	.	.	PUNCT
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eurjchem-205	157	29	.	.	PUNCT
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eurjchem-205	160	4	.	.	PUNCT
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eurjchem-205	169	22	m.	m.	PROPN
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eurjchem-205	169	24	.	.	PUNCT
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eurjchem-205	170	2	.	.	PROPN
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eurjchem-205	170	4	.	.	PUNCT
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eurjchem-205	171	2	.	.	PUNCT
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eurjchem-205	172	2	,	,	PUNCT
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eurjchem-205	172	4	,	,	PUNCT
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eurjchem-205	172	6	.	.	PUNCT
eurjchem-205	173	1	[	[	X
eurjchem-205	173	2	21	21	NUM
eurjchem-205	173	3	]	]	PUNCT
eurjchem-205	173	4	.	.	PUNCT
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eurjchem-205	174	20	,	,	PUNCT
eurjchem-205	174	21	s.	s.	PROPN
eurjchem-205	174	22	m.	m.	PROPN
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eurjchem-205	174	24	.	.	PUNCT
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eurjchem-205	175	2	.	.	PUNCT
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eurjchem-205	175	4	.	.	PUNCT
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eurjchem-205	176	2	,	,	PUNCT
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eurjchem-205	176	4	,	,	PUNCT
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eurjchem-205	176	6	.	.	PUNCT
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eurjchem-205	177	3	]	]	PUNCT
eurjchem-205	177	4	.	.	PUNCT
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eurjchem-205	178	6	,	,	PUNCT
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eurjchem-205	178	15	,	,	PUNCT
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eurjchem-205	178	17	;	;	PUNCT
eurjchem-205	178	18	zunino	zunino	PROPN
eurjchem-205	178	19	,	,	PUNCT
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eurjchem-205	178	22	.	.	PUNCT
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eurjchem-205	180	2	.	.	PUNCT
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eurjchem-205	181	2	,	,	PUNCT
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eurjchem-205	181	4	,	,	PUNCT
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eurjchem-205	181	6	.	.	PUNCT
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eurjchem-205	182	2	23	23	NUM
eurjchem-205	182	3	]	]	PUNCT
eurjchem-205	182	4	.	.	PUNCT
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eurjchem-205	183	2	,	,	PUNCT
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eurjchem-205	183	4	;	;	PUNCT
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eurjchem-205	183	6	,	,	PUNCT
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eurjchem-205	184	2	,	,	PUNCT
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eurjchem-205	184	4	,	,	PUNCT
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eurjchem-205	184	6	.	.	PUNCT
eurjchem-205	185	1	[	[	X
eurjchem-205	185	2	24	24	NUM
eurjchem-205	185	3	]	]	PUNCT
eurjchem-205	185	4	.	.	PUNCT
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eurjchem-205	186	2	,	,	PUNCT
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eurjchem-205	186	5	;	;	PUNCT
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eurjchem-205	186	7	,	,	PUNCT
eurjchem-205	186	8	s.	s.	PROPN
eurjchem-205	186	9	;	;	PUNCT
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eurjchem-205	186	12	r.	r.	PROPN
eurjchem-205	186	13	a.	a.	PROPN
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eurjchem-205	186	16	.	.	PUNCT
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eurjchem-205	186	18	,	,	PUNCT
eurjchem-205	186	19	40	40	NUM
eurjchem-205	186	20	,	,	PUNCT
eurjchem-205	186	21	2723‐2724	2723‐2724	NUM
eurjchem-205	186	22	.	.	PUNCT
eurjchem-205	187	1	[	[	X
eurjchem-205	187	2	25	25	NUM
eurjchem-205	187	3	]	]	PUNCT
eurjchem-205	187	4	.	.	PUNCT
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eurjchem-205	188	2	,	,	PUNCT
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eurjchem-205	188	6	,	,	PUNCT
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eurjchem-205	188	8	;	;	PUNCT
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eurjchem-205	188	16	,	,	PUNCT
eurjchem-205	188	17	1523‐	1523‐	NUM
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eurjchem-205	188	19	.	.	PUNCT
eurjchem-205	189	1	[	[	X
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eurjchem-205	189	3	]	]	PUNCT
eurjchem-205	189	4	.	.	PUNCT
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eurjchem-205	190	2	,	,	PUNCT
eurjchem-205	190	3	d.	d.	PROPN
eurjchem-205	190	4	;	;	PUNCT
eurjchem-205	190	5	stevenson	stevenson	PROPN
eurjchem-205	190	6	,	,	PUNCT
eurjchem-205	190	7	p.	p.	PROPN
eurjchem-205	190	8	j.	j.	PROPN
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eurjchem-205	191	2	,	,	PUNCT
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eurjchem-205	191	4	,	,	PUNCT
eurjchem-205	191	5	5469‐5470	5469‐5470	NUM
eurjchem-205	191	6	.	.	PUNCT
eurjchem-205	192	1	[	[	X
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eurjchem-205	192	3	]	]	SYM
eurjchem-205	192	4	.	.	PUNCT
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eurjchem-205	193	2	,	,	PUNCT
eurjchem-205	193	3	s.	s.	PROPN
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eurjchem-205	193	9	p.	p.	PROPN
eurjchem-205	193	10	j.	j.	PROPN
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eurjchem-205	193	12	.	.	PUNCT
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eurjchem-205	193	14	.	.	PUNCT
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eurjchem-205	194	2	,	,	PUNCT
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eurjchem-205	194	4	,	,	PUNCT
eurjchem-205	194	5	4563‐4566	4563‐4566	NUM
eurjchem-205	194	6	.	.	PUNCT
eurjchem-205	195	1	[	[	X
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eurjchem-205	195	3	]	]	PUNCT
eurjchem-205	195	4	.	.	PUNCT
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eurjchem-205	196	2	,	,	PUNCT
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eurjchem-205	196	6	,	,	PUNCT
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eurjchem-205	196	10	.	.	PUNCT
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eurjchem-205	197	2	.	.	PUNCT
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eurjchem-205	198	2	,	,	PUNCT
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eurjchem-205	198	4	,	,	PUNCT
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eurjchem-205	198	6	.	.	PUNCT
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eurjchem-205	199	3	]	]	PUNCT
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eurjchem-205	199	12	;	;	PUNCT
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eurjchem-205	200	2	,	,	PUNCT
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eurjchem-205	200	4	,	,	PUNCT
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eurjchem-205	200	6	.	.	PUNCT
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eurjchem-205	201	3	]	]	PUNCT
eurjchem-205	201	4	.	.	PUNCT
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eurjchem-205	202	2	,	,	PUNCT
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eurjchem-205	202	5	;	;	PUNCT
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eurjchem-205	202	7	,	,	PUNCT
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eurjchem-205	202	17	.	.	PUNCT
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eurjchem-205	203	2	,	,	PUNCT
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eurjchem-205	203	4	,	,	PUNCT
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eurjchem-205	203	6	.	.	PUNCT
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eurjchem-205	204	3	]	]	PUNCT
eurjchem-205	204	4	.	.	PUNCT
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eurjchem-205	205	2	,	,	PUNCT
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eurjchem-205	205	4	;	;	PUNCT
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eurjchem-205	205	6	,	,	PUNCT
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eurjchem-205	205	10	.	.	PUNCT
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eurjchem-205	206	2	,	,	PUNCT
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eurjchem-205	206	4	,	,	PUNCT
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eurjchem-205	210	2	,	,	PUNCT
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eurjchem-205	210	6	.	.	PUNCT
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eurjchem-205	211	4	.	.	PUNCT
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eurjchem-205	212	22	m.	m.	PROPN
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eurjchem-205	212	24	.	.	PUNCT
eurjchem-205	213	1	lett	lett	PROPN
eurjchem-205	213	2	.	.	PUNCT
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eurjchem-205	214	2	,	,	PUNCT
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eurjchem-205	214	4	,	,	PUNCT
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eurjchem-205	214	6	.	.	PUNCT
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eurjchem-205	215	3	]	]	PUNCT
eurjchem-205	215	4	.	.	PUNCT
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eurjchem-205	216	2	,	,	PUNCT
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eurjchem-205	216	30	.	.	PUNCT
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eurjchem-205	218	2	.	.	PUNCT
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eurjchem-205	219	2	,	,	PUNCT
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eurjchem-205	225	25	.	.	PUNCT
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eurjchem-205	227	2	,	,	PUNCT
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eurjchem-205	231	28	.	.	PUNCT
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eurjchem-205	233	2	,	,	PUNCT
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eurjchem-205	235	28	.	.	PUNCT
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eurjchem-205	236	2	,	,	PUNCT
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