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European	Journal	of	Chemistry	3	(4)	(2012)	455‐460	

European	Journal	of	Chemistry	
ISSN	2153‐2249	(Print)	/	ISSN	2153‐2257	(Online)		2012	EURJCHEM	

DOI:10.5155/eurjchem.3.4.455‐460.683	

	
	

	

	

European	Journal	of	Chemistry	
Journal	homepage:	www.eurjchem.com	

	 	 	

Synthesis	and	antimicrobial	activities	of	pyrido[2,3‐d]pyrimidine,	
pyridotriazolopyrimidine,	triazolopyrimidine,	and		
pyrido[2,3‐d:6,5d']dipyrimidine	derivatives	

Anhar	Abdel‐Aziem	a,	Marwa	Sayed	El‐Gendy	a	and	Abdou	Osman	Abdelhamid	b,*	

a	Department	of	Chemistry,	Faculty	of	Science	(Girls),	Azhar	University,	Nasr	City,	Cairo,	11754,	Egypt	
b	Department	of	Chemistry,	Faculty	of	Science,	Cairo	University,	Giza,	12613,	Egypt	

*Corresponding	author	at:	Department	of	Chemistry,	Faculty	of	Science,	Cairo	University,	Giza,	12613,	Egypt.		
Tel.:	+20.2.1005205750;	Fax:	+20.2.35676573.	E‐mail	address:	abdelhamid45@gmail.com	(A.O.	Abdelhamid).	

	
	

	 	

	 	 	
ARTICLE	INFORMATION	 	 ABSTRACT	
Received:	25	September	2012	
Received	in	revised	form:	25	October	2012	
Accepted:	30	October	2012	
Online:	31	December	2012	

KEYWORDS	

	 A	 new	 series	 of	 pyridotriazolopyrimidines were synthesized	 via	 reaction	 of	 hydrazonoyl
halides	with	 pyrido[2,3‐d]pyrimidines.	 The	 structures	 of	 the	 newly	 synthesized	 compounds
were	 established	 by	 elemental	 analysis,	 spectral	 data	 and	 alternative	 synthetic	 routes
whenever	 possible.	 Some	 of	 synthesized	 compounds	 were	 also	 screened	 in	 vitro	 for	 their
antimicrobial	activity	against	a	variety	of	bacterial	and	fungal	samples.	

Nitrile	imines	
6‐Aminothiouracil	
Pyridopyrimidines	
Hydrazonoyl	halides	
Pyridotriazolopyrimidines	
Pyrido[2,3‐d:6,5d']dipyrimidine	

	
1.	Introduction	
	

Previously,	 it	 was	 reported	 that	 pyrido[2,3‐d]pyrimidines	
possess	abroad	spectrum	of	biological	activity.	They	are	used	as	
antiallergic	 [1],	 antiasmatic	 agents	 [2],	 antihypertensive	 [3],	
anti‐inflammatory	 [4],	 anticancer	 and	 antiviral	 [5‐8],	 diuretic	
[9]	 and	 anticancer	 agents	 [10,11].	 Other	 than	 their	 biological	
importance,	 they	 are	 valuable	 for	 synthesis	 of	 polyfunctional	
heterocyclic	compounds.	As	an	extension	of	our	study	 [12‐18]	
and	 our	 program	 aiming	 at	 the	 synthesis	 of	 different	
heterocyclic	 derivatives,	 we	 report	 herein	 the	 convenient	
synthesis	 of	 some	 new	 triazolo[4,3‐a]pyrimidin‐5(H)‐one,	
pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐5‐one	 and	 1,2,4‐
triazolino[4,5‐a]‐1,2,4‐triazolino[4'',5''‐1',2']pyrimidino[5',4'‐5,	
6]pyridino[2,3‐d]pyrimidin‐4,6‐dione	derivatives.		
	
2.	Experimental	
	
2.1.	Instrumentation	
	

All	 melting	 points	 were	 determined	 on	 an	 electrothermal	
apparatus	and	are	uncorrected.	IR	spectra	were	recorded	(KBr	
discs)	on	a	Shimadzu	FT‐IR	8201	PC	spectrophotometer.	1H	and	
13C	 NMR	 spectra	 were	 recorded	 in	 CDCl3	 and	 (CD3)2SO	
solutions	 on	 a	 Varian	 Gemini	 300	 MHz	 and	 JNM‐LA	 400	 FT‐
NMR	system	spectrometer	and	chemical	shifts	are	expressed	in	
	 ppm	units	using	TMS	as	an	 internal	 reference.	Mass	spectra	
were	 recorded	 on	 a	 GC‐MS	 QP1000	 EX	 Shimadzu.	 Elemental	
analyses	 were	 carried	 out	 at	 the	 Micro	 analytical	 Center	 of	
Cairo	 University.	 Hydrazonoyl	 halides	 5a‐e	 [19‐23]	 were	
prepared	as	previously	reported.		
	

2.2.	Synthesis	
		
2.2.1.	Synthesis	of	pyrido[2,3‐d]	pyrimidines	(4a‐c)	
	

A	mixture	 of	 equimolecular	 amounts	 of	 6‐amino‐2‐thioxo‐
2,3‐dihydro‐1H‐pyrimidin‐4‐one	 [24]	 (1)	 (5	 mmol)	 and	 the	
appropriate	 of	 2‐benzylidenemalononitrile	 (2a),	 2‐(benzo[d]	
thiazol‐2‐yl)3‐phenylacrylonitrile	 (2b)	 and	 3‐phenyl‐2‐(4‐
phenylthiazol‐2‐yl)	 acrylonitrile	 (2c)	 (5	 mmol)	 in	 absolute	
ethanol	(10	mL)	containing	triethylamine	(3	drops)	was	heated	
under	 reflux	 for	 3	 h.	 The	 reaction	 mixture	 was	 concentrated	
and	 cooled.	 The	 solid	 obtained	 was	 filtered	 off,	 washed	 with	
ethanol	and	recrystallized	from	N,N‐dimethylformamide	to	give	
4a‐c,	respectively	(Scheme	1).	

	

Scheme	1	
	
	



456	 Abdel‐Aziem	et	al.	/	European	Journal	of	Chemistry	3	(4)	(2012)	455‐460	
	

7‐Amino‐1,2,3,4‐tetrahydro‐4‐oxo‐5‐phenyl‐2‐thioxopyrido	
[2,3‐d]pyrimidine‐6‐carbonitrile	 (4a)	 [25]:	 Color:	 Pale	 yellow	
(from	N,N‐dimethylformamide).	Yield:	80%.	M.p.:	>300	oC.	FT‐
IR	 (KBr,	,	 cm‐1):	3439,	3320	 (NH2,	NH),	3058	 (CH,	aromatic),	
2214	 (CN),	1639	(CO),	1616	 (C=N),	1527	(C=C).	 1H	NMR	(300	
MHz,	 CDCl3,	 δ,	 ppm):	 7.72	 (s.,	 br.,	 2H,	NH2),	 7.42‐7.40	 (m,	 7H,	
ArH's	and	NH).	Anal.	calcd.	for	C14H9N5OS:	C,	56.94;	H,	3.07;	N,	
23.71;	S,	10.86.	Found:	C,	57.11;	H,	3.14;	N,	23.85;	S,	11.00%.	

7‐Amino‐4‐oxo‐5‐phenyl‐6‐(benzo[d]thiazol‐2‐yl)‐2‐thioxo‐1,	
2,3,4‐tetrahydro	 pyrido[2,3‐d]pyrimidine	 (4b):	 Color:	 Pale	
yellow	(from	N,N‐dimethylformamide).	Yield:	80%.	M.p.:	>300	
oC.	 FT‐IR	 (KBr,	,	 cm‐1):	 3250	 (brs,	NH),	 3058	 (CH,	 aromatic),	
1639	(C=O),	1616	(C=N),	1527	(C=C).	1H	NMR	(300	MHz,	CDCl3,	
δ,	 ppm):	 5.78	 (s,	 br,	 2H,	NH2),	 6.74‐7.13	 (m,	 10H,	 ArH's,	 NH),	
12.01	(s,	1H,	NH).	Anal.	calcd.	for	C20H13N5OS2:	C,	59.54;	H,	3.25;	
N,	17.36;	S,	15.89.	Found:	C,	59.49;	H,	3.30;	N,	17.40	S,	15.95%.	

7‐Amino‐4‐oxo‐5‐phenyl‐6‐(phenylthiazol‐2‐yl)‐2‐thioxo‐1,2,	
3,4‐tetrahydro	 pyrido[2,3‐d]pyrimidine	 (4c):	 Color:	 Orange	
(from	N,N‐dimethylformamide).	 Yield:	 80%.	M.p.:	 230‐232	 oC.	
FT‐IR	 (KBr,	 ,	 cm‐1):	 3301,	 3224,	 3136	 (NH,	 NH2),	 3070	 (CH,	
aromatic),	1697	(C=O),	1627	(C=N),	1593	(C=C).	1H	NMR	(300	
MHz,	CDCl3,	δ,	ppm):	6.88‐6.91	 (s,	br.,	2H,	NH2),	7.22‐7.81	 (m,	
12H,	ArH's,	thiazole	H‐5,	NH	and	NH2),	13.00	(s,	1H,	NH).	Anal.	
calcd.	 for	 C22H15N5OS2:	 C,	 61.52;	 H,	 3.52;	 N,	 16.31;	 S,	 14.93.	
Found:	C,	61.45;	H,	3.47;	N,	16.26;	S,	15.00%.		
	
2.2.2.	Synthesis	of	compounds	10a‐e,	11a‐e	and	12a‐d	
	

Method	A:	A	mixture	of	the	appropriate	4a‐c	(5	mmol),	the	
appropriate	 hydrazonoyl	 halides	 5a‐e	 (5	 mmol)	 and	
triethylamine	 (5	 mmol)	 in	 chloroform	 were	 heated	 under	
reflux	 for	 10	 hrs.	 The	 excess	 solvent	was	 evaporated	 and	 the	
residue	was	triturated	with	ethanol	(10	mL).	The	solid	formed	
was	 filtered	off	 and	crystallized	 from	a	proper	 solvent	 to	give	
10‐12,	respectively	(Scheme	2).	

Method	B:	Equimolar	 amounts	 of	 the	 appropriate	4a‐c	 (5	
mmol),	the	appropriate	hydrazonoyl	halides	5a‐e	(5	mmol)	and	
sodium	ethoxide	(5	mmol)	in	ethanol	(20	mL)	were	refluxed	for	
3	h.	 The	 reaction	mixture	was	 cooled;	 the	 resulting	 solid	was	
collected	 and	 recrystallized	 from	 a	 proper	 solvent	 to	 give	
products	identical	in	all	aspects	(M.p.,	mixed	m.p.,	and	spectra)	
with	 the	 corresponding	 products	 obtained	 by	 method	 A	
(Scheme	2).	 

8‐Amino‐3‐(benzofuran‐2‐yl‐carbonyl)‐7‐cyano‐5‐oxo‐1,6‐di‐
phenyl‐1,5‐dihydropyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine	
(10a):	Color:	Red	(from	ethanol).	Yiled:	82%.	M.p.:	148‐150	°C.	
FT‐IR	 (KBr,	 ,	 cm‐1):	 3300,	 3197	 (NH2),	 3055	 (CH,	 aromatic),	
2214	(CN),	1650	(C=O),	1612	(C=N),	1531	(C=C).	1H	NMR	(300	
MHz,	 DMSO‐d6,	 δ,	 ppm):	 6.28	 (s,	 br.,	 2H,	 NH2),	 7.15‐8.21	 (m,	
15H,	 ArH's).	 Anal.	 calcd.	 for	 C30H17N7O3:	 C,	 68.83;	 H,	 3.27;	 N,	
18.73.	Found:	C,	68.73;	H,	3.20;	N,	18.60%.		

Ethyl	8‐amino‐7‐cyano‐5‐oxo‐1,6‐diphenyl‐1,5‐dihydropyrido	
[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine‐3‐carboxylate	 (10b):	
Color:	White	(from	acetic	acid).	Yield:	75%.	M.p.:	>	300	°C.	FT‐
IR	(KBr,	,	cm‐1):	3295,	3190	(NH2),	3062	(CH,	aromatic),	2221	
(CN)	1751,	1716	(C=O),	1620	(C=N),	1546	(C=C).	1H	NMR	(300	
MHz,	DMSO‐d6,	δ,	ppm):	1.21	(t,	3H,	J	=	7.5	Hz,	CH3),	4.37	(q,	2H,	
J	=	7.5	Hz,	CH2),	7.33‐8.14	(m,	12H,	ArH's+NH2).	Anal.	calcd.	for	
C24H17N7O3:	C,	63.85;	H,	3.80;	N,	21.72.	Found:	C,	63.78;	H,	3.88;	
N,	21.65%.		

8‐Amino‐3‐acetyl‐7‐cyano‐5‐oxo‐1,6‐diphenyl‐1,5‐dihydro	
pyrido[2,3‐d][1,2,4]triazolo‐[4,3‐a]pyrimidine	 (10c):	 Color:	 Red	
(from	ethanol).	Yield:	75%.	M.p.:	180‐182	°C.	FT‐IR	(KBr,	,	cm‐

1):	 3336,	 3205	 (NH2),	 3062	 (CH,	 aromatic),	 2214	 (CN)	 1665,	
1650	 (C=O),	 1612	 (C=N),	 1531	 (C=C).	 1H	 NMR	 (300	 MHz,	
DMSO‐d6,	 δ,	 ppm):	 2.73	 (s,	 3H,	 COCH3),	 7.12‐7.48	 (m,	 12H,	
ArH's	and	NH2).	Anal.	calcd.	for	C23H15N7O2:	C,	65.55;	H,	3.59;	N,	
23.27.	Found:	C,	65.61;	H,	3.51;	N,	23.20%.		

	

8‐Amino‐3‐benzoyl‐7‐cyano‐5‐oxo‐1,6‐diphenyl‐1,5‐dihydro	
pyrido[2,3‐d][1,2,4]triazolo‐[4,3‐a]pyrimidine	 (10d):	Color:	 Red	
(from	ethanol).	Yield:	78%.	M.p.:	189‐190	°C.	FT‐IR	(KBr,	,	cm‐

1):	 3332,	 3182	 (NH2),	 3062	 (CH,	 aromatic),	 2218	 (CN),	 1640	
(C=O),	1624	(C=N),	1546	(C=C).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	
ppm):	 4.44	 (s,	 br.,	 2H,	 NH2),	 7.25‐8.06	 (m,	 15H,	 ArH's).	 Anal.	
calcd.	 for	 C28H17N7O2:	 C,	 69.56;	 H,	 3.54;	 N,	 20.28.	 Found:	 C,	
69.49;	H,	3.60;	N,	20.20%.		

8‐Amino‐3‐phenylcarbamoyl‐7‐cyano‐5‐oxo‐1,6‐diphenyl‐1,	
5‐dihydropyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine	 (10e):	
Color:	yellow	(from	ethanol).	Yield:	80%.	M.p.:	238‐240	°C.	FT‐
IR	 (KBr,	 ,	 cm‐1):	 3382,	 3163,	 3109	 (NH,	 NH2),	 3058	 (CH,	
aromatic),	 2221(CN)	 1705,1643	 (C=O),	 1600	 (C=N),	 1527	
(C=C).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	7.01‐8.22	(m,	17H,	
ArH's),	 11.71	 (s,	 br,	 1H,	 NH).	 Anal.	 calcd.	 for	 C28H18N8O2:	 C,	
67.46;	H,	3.64;	N,	22.48.	Found:	C,	67.39;	H,	3.59;	N,	22.41%.	

8‐Amino‐3‐(2‐benzofuroyl)‐7‐(benzothiazol‐2‐yl)‐1,6‐di‐
phenylpyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one	
(11a):	Color:	Red	(from	ethanol).	Yield:	80%.	M.p.:	158‐160	°C.	
FT‐IR	 (KBr,	 ,	 cm‐1):	 3200,3110	 (NH2),	 3050	 (CH,	 aromatic),	
1631	(C=O).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	5.19	(s,	br.,	
2H,	 NH2),	 6.92‐8.05	 (m,	 19H,	 ArH's).	 Anal.	 calcd.	 for	
C36H21N7O3S:	 C,	 68.45;	 H,	 3.35;	 N,	 15.52;	 S,	 5.08.	 Found:	 C,	
68.33;	H,	3.46;	N,	15.40;	S,	4.98%.	

Ethyl	 8‐amino‐7‐(benzothiazol‐2‐yl)‐5‐oxo‐1,6‐diphenyl	
pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐3‐carboxylate	
(11b):	 Color:	 Orange	 (from	 N,N‐dimethylformamide).	 Yield:	
80%.	M.p.:	280‐281	°C.	FT‐IR	(KBr,	,	cm‐1):	3332,	3224	(NH2),	
3035	 (CH,	 aromatic),	 1732,	 1635	 (CO's).	 1H	 NMR	 (300	 MHz,	
DMSO‐d6,	δ,	ppm):	1.20	(t,	3H,	J	=	7.5	Hz,	CH3),	4.20	(q,	2H,	J	=	
7.5	Hz,	CH2),	6.76	(br.,	2H,	NH2),	7.13‐8.96	(m,	14H,	ArH's).	MS	
(EI,	m/z	(%)):	561	(M+2,	4.3),	559	(M+,	3.3),	558	(M‐,	11.5),	486	
(24.9),	371	(13.4),	174	(5.7),	134	(10.0,	77	(100.0).	Anal.	calcd.	
for	C30H21N7O3S:	 C,	 64.39;	H,	3.78;	N,	17.52;	 S,	 5.73.	 Found:	C,	
64.46;	H,	3.70;	N,	17.61;	S,	5.65%.	

8‐Amino‐3‐acetyl‐7‐(benzothiazol‐2‐yl)‐1,6‐diphenylpyrido	
[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one	 (11c):	 Color:	
Red	(from	ethanol).	Yield:	83%.	M.p.:	180‐181	°C.	FT‐IR	(KBr,	,	
cm‐1):	 3330,	 3222	 (NH2),	 3038	 (CH,	 aromatic),	 11682,	 1640	
(CO's).	 1H	 NMR	 (300	 MHz,	 DMSO‐d6,	 δ,	 ppm):	 2.31	 (s,	 3H,	
COCH3),	7.12‐7.48	(m,	16H,	ArH's	and	NH2).	MS	(EI,	m/z	 (%)):	
529	(M+,	12.2),	252	(12.2),	240	(6.1),	174	(16.3),	134	(18.4),	57	
(100.0).	Anal.	calcd.	for	C29H19N7O2S:	C,	65.77;	H,	3.62;	N,	18.51;	
S,	6.05.	Found:	C,	65.69;	H,	3.71;	N,	18.43;	S,	6.12%.	

8‐Amino‐3‐benzoyl‐7‐(benzothiazol‐2‐yl)‐1,6‐diphenylpyrido	
[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one	 	 (11d):	 Color:	
Red	 (from	ethanol).	 Yield:	 75%.	M.p.:	 90‐92	 °C.	 FT‐IR	 (KBr,	,	
cm‐1):	3479,	3394	(NH2),	3050	(CH,	aromatic),	1689	(CO),	1593	
(C=N).	 1H	NMR	 (300	MHz,	DMSO‐d6,	 δ,	 ppm):	 5.22	 (s,	 br.,	 2H,	
NH2),	7.12‐8.11	(m,	19H,	ArH's).	Anal.	calcd.	for	C34H21N7O2S:	C,	
69.02;	 H,	 3.58;	 N,	 16.57;	 S,	 5.42.	 Found:	 C,	 69.11;	 H,	 3.50;	 N,	
16.65;	S,	5.50%.	

8‐Amino‐N‐phenyl‐7‐(benzothiazol‐2‐yl)‐5‐oxo‐1,6‐diphenyl	
pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐3‐carboxamide	
(11e):	Color:	Yellow	(from	ethanol).	Yield:	75%.	M.p.:	180‐182	
°C.	FT‐IR	(KBr,	,	cm‐1):	3382,	3159,	3109	(NH,	NH2),	3020	(CH,	
aromatic),	 1647	 (CO),	 1600	 (C=C),	 1531	 (C=C).	 1H	 NMR	 (300	
MHz,	DMSO‐d6,	δ,	ppm):	6.45	(s,	br.,	3H,	NH,	NH2),	7.12‐8.11	(m,	
19H,	ArH's).	Anal.	 calcd.	 for	C34H22N8O2S:	 C,	 67.31;	H,	 3.66;	N,	
18.47;	S,	5.29.	Found:	C,	67.21;	H,	3.60;	N,	18.40;	S,	5.20%.	

8‐Amino‐3‐(2‐benzofuroyl)‐7‐(4‐phenylthiazol‐2‐yl)‐1,6‐di‐
phenylpyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one	
(12a):	Color:	Red	(from	ethanol).	Yield:	80%.	M.p.:	185‐187	°C.	
FT‐IR	 (KBr,	 ,	 cm‐1):	 3425,	 3363	 (NH2),	 3062	 (CH,	 aromatic),	
1660	 (CO).	 1H	NMR	 (300	MHz,	DMSO‐d6,	 δ,	ppm):	4.92	 (s,	 br.,	
2H,	 NH2),	 7.00‐8.18	 (m,	 21H,	 ArH's).	 Anal.	 calcd.	 for	
C38H23N7O3S:	 C,	 69.39;	 H,	 3.52;	 N,	 14.91;	 S,	 4.88.	 Found:	 C,	
69.29;	H,	3.61;	N,	14.78;	S,	4.93%.	

	
	



Abdel‐Aziem	et	al.	/	European	Journal	of	Chemistry	3	(4)	(2012)	455‐460	 457	
 

	

	
	

Scheme	2
	
	
Ethyl	 8‐amino‐7‐(4‐phenylthiazol‐2‐yl)‐5‐oxo‐1,6‐diphenyl	

pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐3‐carboxylate	
(12b):	 Color:	 Yellow	 (from	 N,N‐dimethylformamide).	 Yield:	
85%.	M.p.:	290‐292	°C.	FT‐IR	(KBr,	,	cm‐1):	3471,	3394	(NH2),	
3043	 (CH,	 aromatic),	 1743,	 1697	 (C=O),	 1600	 (C=N),	 1546	
(C=C).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	1.21	(t,	3H,	J	=	7.5	
Hz,	CH3),	4.35	(q,	2H,	J=	7.5	Hz,	CH2),	7.22‐8.20	(m,	18H,	ArH's	
and	 NH2).	 Anal.	 calcd.	 for	 C32H23N7O3S:	 C,	 65.63;	 H,	 3.96;	 N,	
16.74;	S,	5.48.	Found:	C,	65.70;	H,	3.88;	N,	16.82;	S,	5.57%.	

8‐Amino‐3‐acetyl‐7‐(4‐phenylthiazol‐2‐yl)‐1,6‐diphenyl	
pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one	 	 (12c):	
Color:	Red	(from	ethanol).	Yield:	80%.	M.p.:	180‐182	°C.	FT‐IR	

(KBr,	 ,	 cm‐1):	 3471,	 3394	 (NH2),	 3043	 (CH,	 aromatic),	 1697	
(C=O),	1600	(C=C).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	2.10	
(s,	3H,	COCH3),	4.21	(brs,	2H,	NH2),	7.24‐8.02	(m,	16H,	ArH's).	
Anal.	calcd.	for	C31H21N7O2S:	C,	67.01;	H,	3.81;	N,	17.65;	S,	5.77.	
Found:	C,	67.10;	H,	3.89;	N,	17.57;	S,	5.67%.	

8‐Amino‐3‐benzoyl‐7‐(4‐phenylthiazol‐2‐yl)‐1,6‐diphenyl	
pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one	 (12d):	
Color:	Red	(from	ethanol).	Yield:	80%.	M.p.:	110‐112	°C.	FT‐IR	
(KBr,	 ,	 cm‐1):	 3425,	 3386	 (NH2),	 3062	 (CH,	 aromatic),	 1708	
(C=O),	1596	(C=N),	1554	(C=C).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	
ppm):	 4.88	 (s,	 br.,	 2H,	 NH2),	 7.27‐8.30	 (m,	 21H,	 ArH's	 and	



458	 Abdel‐Aziem	et	al.	/	European	Journal	of	Chemistry	3	(4)	(2012)	455‐460	
	
thiazole	H‐5).	Anal.	calcd.	for	C36H23N7O2S:	C,	70.00;	H,	3.75;	N,	
15.87;	S,	5.19.	Found:	C,	70.10;	H,	3.65;	N,	15.77;	S,	5.27%.	
	
2.2.3. 7‐amino‐3‐(2‐benzofuroyl)‐1‐phenyl‐[1,2,4]triazolo	
[4,3‐a]pyrimidin‐5(1H)‐one	(13)	
	

A	 mixture	 of	 compound	 1	 (5	 mmol),	 the	 appropriate	
hydrazonoyl	halides	5a	(5	mmol)	and	triethylamine	 (5	mmol)	
in	chloroform	were	heated	under	reflux	for	10	hrs.	The	excess	
solvent	 was	 evaporated	 and	 the	 residue	 was	 triturated	 with	
ethanol	 (10	 mL).	 The	 solid	 formed	 was	 filtered	 off	 and	
crystallized	 from	 ethanol	 to	 give	 compound	 13	 (Scheme	 2).	
Color:	Red	(from	ethanol).	Yield:	80%.	M.p.:	150‐152	°C.	FT‐IR	
(KBr,	 ,	 cm‐1):	 3421,	 3379	 (NH2),	 3055	 (CH,	 aromatic),	 1631	
(C=O).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	4.94	(s,	1H,	H‐6),	
6.21	(s,	br.,	2H,	NH2),	7.39‐8.51	(m,	10H,	ArH's).	Anal.	calcd.	for	
C20H13N5O3:	C,	64.69;	H,	3.53;	N,	18.86.	Found:	C,	64.60;	H,	3.47;	
N,	18.78%.	
	
2.2.4.	Alternative	synthesis	of	compounds	10‐12	
	

A	 mixture	 of	 the	 appropriate	 13a‐e	 7‐amino‐1‐phenyl‐5‐
oxo‐1,2,4‐triazolo[4,3‐a]pyrimidine	 [26]	13	 (5	mmol)	 and	 the	
appropriate	of	arylidene	2a‐c	(5	mmol)	in	absolute	ethanol	(10	
mL)	containing	triethylamine	was	heated	under	reflux	for	3	h.	
The	 reaction	mixture	was	 concentrated	 and	 cooled.	 The	 solid	
obtained	 was	 filtered	 off,	 washed	 with	 ethanol	 and	
recrystallized	 from	a	proper	solvent	to	give	products	 identical	
in	 all	 aspects	 (M.p.,	 mixed	 m.p.	 and	 spectra)	 with	 the	
corresponding	products	obtained	by	method	A	(Scheme	2).		
	
2.2.5.	10‐(1,3‐Diphenyl‐1H‐pyrazol‐4‐yl)‐2,7‐dithioxo‐
2,3,7,8,9,10‐hexahydro‐1H,6H‐1,3,6,8,9‐pentaaza‐
anthracene‐4,5‐dione	(15)	
	

To	 a	 solution	 of	 6‐amino	 thiouracil	 (1),	 (5	 mmol)	 in	
methanol	 (10	 mL)	 and	 concentrated	 hydrochloric	 acid	 (0.4	
mL),	compound	14	was	added	and	stirred	at	room	temperature	
for	4	h,	 the	solid	 that	obtained	was	collected	by	 filtration	and	
crystallized	from	N,N‐dimethylformamide	to	give	compound	15	
(Scheme	 3).	 Color:	 Orange.	 Yield:	 75%.	 M.p.:	 >300	 °C.	 FT‐IR	
(KBr,,	 cm‐1):	 3444,	 3321,	 3200	 (NH),	 3058	 (CH,	 aromatic),	
1654	(C=O).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	4.76	(s,	1H,	
CH),	7.24‐7.82	(m,	11H,	ArH's	and	pyrazole	H‐5)),	11.95	(s,	2H,	
2NH),	 14.07	 (s,	 br.,	 3H,	 3NH).	 13C	 NMR	 (75	MHz,	DMSO‐d6,	 δ,	
ppm):	 21.65,	 100.11,	 115.21,	 122.64,	 124.23,	 125.85,	 127.35,	
127.89,	 129.42,	 136.472,	 137.54,	 138.29,	 145.11,	 155.20,	
172.98.	Anal.	calcd.	for	C24H17N7O2S2:	C,	57.70;	H,	3.43;	N,	19.63;	
S,	12.84.	Found:	C,	57.62;	H,	3.34;	N,	19.53;	S,	12.93%.	
	
	

	
	

Scheme	3	

2.2.6.	Synthesis	of	compounds	16a‐c	
	

A	 mixture	 of	 compound	 15	 (5	 mmol),	 the	 appropriate	
hydrazonoyl	halides	5a‐c	(5	mmol)	and	triethylamine	(5	mmol)	
in	chloroform	were	heated	under	reflux	for	10	hrs.	The	excess	
solvent	 was	 evaporated	 and	 the	 residue	 was	 triturated	 with	
ethanol	 (10	 mL).	 The	 solid	 formed	 was	 filtered	 off	 and	
crystallized	 from	 a	 proper	 solvent	 to	 give	16a‐c,	 respectively	
(Scheme	3).	

3,7‐Bis‐(benzofuran‐2‐carbonyl)‐5‐(1,3‐diphenyl‐1H‐pyrazol‐
4‐yl)‐1,9‐diphenyl‐5,11‐dihydro‐1H,9H‐1,2,3a,6a,8,9,10,11,12‐
nonaaza‐dicyclopenta[b,i]anthracene‐4,6‐dione	 (16a):	 Color:	
Red	(from	ethanol).	Yield:	75%.	M.p.:	202‐204	°C.	FT‐IR	(KBr,	,	
cm‐1):	 3328	 (NH),	 3062	 (CH,	 aromatic),	 1662	 (CO).	 1H	 NMR	
(300	MHz,	 DMSO‐d6,	 δ,	 ppm):	 4.45	 (s,	 1H,	 CH),	 7.01‐8.23	 (m,	
31H,	ArH's),	11.88	(s,	br.,	1H,	NH).	Anal.	calcd.	for	C56H33N11O6:	
C,	70.36;	H,	3.48;	N,	16.12.	Found:	C,	70.26;	H,	3.39;	N,	16.03%. 

5‐(1,3‐Diphenyl‐1H‐pyrazol‐4‐yl)‐4,6‐dioxo‐1,9‐diphenyl‐
5,6,9,11‐tetrahydro‐1H,4H‐1,2,3a,6a,8,9,10,11,12‐nonaaza‐
dicyclopenta[b,i]anthracene‐3,7‐dicarboxylic	 acid	 diethyl	 ester	
(16b):	Color:	Orange	(from	ethanol).	Yield:	80%.	M.p.:	180‐182	
°C.	FT‐IR	(KBr,	,	cm‐1):	3328	(NH),	3062	(CH,	aromatic),	1735,	
1674	 (CO's),	 1647	 (C=N),	 1600	 (C=C).	 1H	 NMR	 (300	 MHz,	
DMSO‐d6,	 δ,	ppm):	1.07	 (t,	 6H,	 J	 =	7Hz,	 2CH3),	4.40	 (q,	4H,	 J	 =	
7Hz,	2CH2),	6.20	(s,	1H,	CH‐9),	6.88‐8.08	(m,	21H,	ArH's),	11.27	
(s,	 1H,	 NH).	 Anal.	 calcd.	 for	 C44H33N11O6:	 C,	 65.10;	 H,	 4.10;	 N,	
18.98.	Found:	C,	65.19;	H,	4.00;	N,	18.89%.	

3,7‐Diacetyl‐5‐(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐1,9‐diphenyl‐
5,11‐dihydro‐1H,9H‐1,2,3a,6a,8,9,10,11,12‐nonaaza‐dicyclo	
penta[b,i]anthracene‐4,6‐dione	 (16c):	 Color:	 Orange	 (from	
ethanol).	 Yield:	 83%.	 M.p.:	 268‐270	 °C.	 FT‐IR	 (KBr,	 ,	 cm‐1):	
3394	(NH),	3058	(CH,	aromatic),	1631	(CO).	1H	NMR	(300	MHz,	
DMSO‐d6,	δ,	ppm):	2.72	(s,	6H,	2CH3CO),	5.12	(s,	1H,	CH),	7.12‐
8.11	 (m,	 21H,	 ArH's),	 11.87	 (s,	 br.,	 1H,	 NH).	 Anal.	 calcd.	 for	
C42H29N11O4:	 C,	 67.10;	 H,	 3.89;	 N,	 20.50.	 Found:	 C,	 67.19;	 H,	
3.80;	N,	20.42%.	
	
2.2.7.	Synthesis	of	compound	18a‐c	
		

A	mixture	of	compound	17	 [27]	(5	mmol),	the	appropriate	
hydrazonoyl	halides	5a‐c	(5	mmol)	and	triethylamine	(5	mmol)	
in	chloroform	were	heated	under	reflux	for	10	hrs.	The	excess	
solvent	 was	 evaporated	 and	 the	 residue	 was	 triturated	 with	
ethanol	 (10	 mL).	 The	 solid	 formed	 was	 filtered	 off	 and	
crystallized	 from	 a	 proper	 solvent	 to	 give	 compound	 18a‐c,	
respectively	(Scheme	4).	

3,7‐Bis‐(benzofuran‐2‐carbonyl)‐1,9‐diphenyl‐5,11‐dihydro‐
1H,9H‐1,2,3a,6a,8,9,10,11,12‐nonaaza‐dicyclopenta[b,i]anthrax‐
cene‐4,6‐dione	(18a):	Color:	White	 (from	ethanol).	Yield:	70%.	
M.p.:	 158‐160	 °C.	 FT‐IR	 (KBr,	 ,	 cm‐1):	 3120	 (NH)	 1724,	
1681(C=O),	1604	(C=C).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	
3.66	 (s,	 2H,	 CH2),	 7.17‐8.12	 (m,	 20H,	ArH's),	 11.87	 (s,	 br.,	 1H,	
NH).	 Anal.	 calcd.	 for	 C41H23N9O6:	 C,	 66.76;	 H,	 3.14;	 N,	 17.09.	
Found:	C,	66.68;	H,	3.24;	N,	17.12%.		

4,6‐Dioxo‐1,9‐diphenyl‐5,6,9,11‐tetrahydro‐1H,4H‐1,2,3a,6a,	
8,9,10,11,12‐nonaaza‐dicyclopenta[b,i]‐anthracene‐3,7‐dicar‐
boxylic	 acid	 diethyl	 ester	 (18b):	 Color:	 Yellow	 (from	 ethanol).	
Yield:	70%.	M.p.:	138‐140	°C.	FT‐IR	(KBr,	,	 cm‐1):	3386	(NH),	
1747	(C=O	ester),	1681	(C=O),	1600	(C=N).	1H	NMR	(300	MHz,	
DMSO‐d6,	δ,	ppm):	1.14	(t,	6H,	J	=	7	Hz,	2CH3),	3.56	(s,	2H,	CH2),	
4.13	(q,	4H,	J	=	7	Hz,	2CH2),	6.99‐7.35	(m,	10H,	ArH's),	10.8	(s,	
1H,	NH).	Anal.	calcd.	for	C29H23N9O6:	C,	58.68;	H,	3.91;	N,	21.24.	
Found:	C,	58.78;	H,	4.00;	N,	21.31%.	

3,7‐Diacetyl‐1,9‐diphenyl‐5,11‐dihydro‐1H,9H‐1,2,3a,6a,8,9,	
10,11,12‐nonaaza‐dicyclopenta[b,i]anthracene‐4,6‐dione	 (18c):	
Color:	White	(from	ethanol).	Yield:	68%.	M.p.:	200‐202	°C.	FT‐
IR	(KBr,	,	cm‐1):	3120	(NH),	1724,	1681(C=O),	1604	(C=N).	1H	
NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	2.35	(s,	6H,	2CH3),	3.65	(s,	
2H,	CH2),	7.02‐7.54	(m,	10H,	ArH's),	12.08	(s,	1H,	NH).		

	



Abdel‐Aziem	et	al.	/	European	Journal	of	Chemistry	3	(4)	(2012)	455‐460	 459	
 

	
Table	1.	The	antimicrobial	activity	of	the	newly	synthesized	compounds	*.	

Sample	No	

Microorganism	/	Mean	of	zone	diameter,	nearest	whole	mm	
Gram‐positive	bacteria	 Gram‐negative	bacteria Fungi
Bacillus	Subtilis	
(ATCC	6635)	

Escherichia	coli	
(ATCC	25922)	

Candida	Albicans	
(ATCC	10231)	

Aspergillus	
Fumigatus	

1	mg/mL	 0.5	mg/mL	 1	mg/mL 0.5	mg/mL 1	mg/mL 1	mg/mL 1	mg/mL	 0.5	mg/mL
4a	 11	(L)	 7	(L)	 ‐	 ‐ ‐ ‐ ‐	 ‐	
4b	 13	(L)	 7	(L)	 ‐	 ‐ 13	(I) 10	(I) 12	(I)	 8	(I)
4c	 10	(L)	 8	(L)	 ‐	 ‐ ‐ ‐ ‐	 ‐	
10b	 ‐	 ‐	 12	(I) 7	(I) ‐ ‐ 11	(L)	 7	(L)
10c	 ‐	 ‐	 ‐	 ‐ ‐ ‐ ‐	 ‐	
11a	 ‐	 ‐	 14	(I)	 11	(I)	 ‐	 ‐	 ‐	 ‐	
11c	 ‐	 ‐	 ‐	 ‐ ‐ ‐ ‐	 ‐	
12a	 11	(L)	 8	(L)	 ‐	 ‐	 ‐	 ‐	 ‐	 ‐	
12c	 ‐	 ‐	 ‐	 ‐	 ‐	 ‐	 ‐	 ‐	
18a	 ‐	 ‐	 ‐	 ‐	 ‐	 ‐	 ‐	 ‐	
18b	 10	(L)	 7	(L)	 ‐	 ‐ 11	(L) 7	(L) ‐	 ‐	
Control	#	 35	 38	 38 27 35 35 37	 26
*	Identified	on	the	basis	of	routine	culture,	morphological	and	microscopical	characteristics:	‐	=	No	effect,	L:	Low	activity	(Mean	of	zone	diameter	≤1/3	of	mean	
zone	diameter	of	control),	I:	intermediate	activity	=	(Mean	of	zone	diameter	≤2/3	of	mean	zone	diameter	of	control),	H:	High	activity	=	(Mean	of	zone	diameter	
>2/3	of	mean	zone	diameter	of	control).	
#	Chloramphencol	in	the	case	of	Gram‐positive	bacteria,	Cephalothin	in	the	case	of	Gram‐negative	bacteria	and	Cycloheximide	in	the	case	of	fungi.	

	
	

Anal.	calcd.	for	C27H19N9O4:	C,	60.79;	H,	3.59;	N,	23.63.	Found:	C,	
60.70;	H,	3.50;	N,	23.54%.	
	

NNHPh

X
O

R

N

N

N
H

N

N

N
N N

N

O O

PhPh

ROC COR

18
17

N
H

HN

N
H

N
H

NH

OO

SS

5a, R = benzofuran-2-yl
b, R = OC2H5
c, R = CH3

N

N

H2N N
N

O

Ph

COR

CH2O, HCl

5a-c

13

	
Scheme	4	

	
2.3.	Antimicrobial	activity	
	

The	 tested	 compounds	 were	 dissolved	 in	 DMF	 and	
prepared	 in	 two	concentrations;	50	and	100	mg/mL	and	 then	
10	 μL	 of	 each	 preparation	 was	 dropped	 on	 disk	 of	 6	 mm	 in	
diameter	 and	 the	 concentrations	 became	 0.5	 and	 1.0	mg/mL,	
respectively.	Uniform	size	filter	paper	disks	(6	mm	in	diameter)	
were	 impregnated	 by	 volume	 (10	 μL)	 from	 the	 specific	
concentration	of	dissolved	compounds	and	carefully	placed	on	
inoculated	agar	surface.	After	incubation	for	36	hrs	at	27	°C	in	
the	case	of	bacteria	and	for	48	hrs	at	24	°C	in	the	case	of	fungi,	
inhibition	 of	 the	 organisms	 which	 evidenced	 by	 clear	 zone	
surround	each	disk	was	measured	and	used	to	calculate	mean	
of	inhibition	zone	[28].	
	
3.	Results	and	discussion 
	
3.1.	Synthesis	
	

Condensation	of	6‐aminothiouracil	(1)	with	the	appropriate	
amount	of	benzylidene	malononitril	(2a),	2‐(benzo[d]thiazol‐2‐
yl)‐3‐phenylacrylonitrile	 (2b)	 and	 3‐phenyl‐2‐(4‐phenyl‐
thiazol‐2‐yl)acrylonitrile	 (2c)	 in	 ethanol	 containing	 triethyl‐
amine	 under	 reflux	 gave	 7‐amino‐6‐substituted	 5‐phenyl‐2,3‐
dihydro‐2‐thioxo‐pyrido[2,3‐d]	 pyrimidin‐4(1H)‐one,	 4a‐c,	
respectively	 (Scheme	 1).	 Structures	 4a‐c	 were	 confirmed	 by	
elemental	analyses,	spectral	data	and	chemical	transformation.		

Thus,	 treatment	 of	 pyrido[2,3‐d]	 pyrimidine	derivative	4a	
with	 C‐benzofuran‐2oyl‐N‐phenylhydrazonoyl	 bromide	 5a	 in	
boiling	chloroform	containing	triethylamine	afforded	8‐Amino‐

3‐(benzofuran‐2‐yl‐carbonyl)‐7‐cyano‐5‐oxo‐1,6‐diphenyl‐1,5‐
dihydropyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine	 (10a).	
Structure	 of	 compound	 10a	 was	 elucidated	 via	 elemental	
analysis,	spectral	data	and	alternative	synthesis.	Thus,	reaction	
of	compound	2a	with	7‐amino‐3‐(1‐benzofuran‐2‐yl‐carbonyl)‐
1‐phenyl[1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one	 (13a),	
which	 was	 prepared	 via	 reaction	 of	 compound	 1	 with	
compound	5a,	 in	boiling	ethanolic	 triethylamine	gave	product	
identical	 in	 all	 aspects	 (M.p.,	 mixed	 m.p.,	 and	 spectra)	 with	
compound	10a.		

The	mechanism	outlined	in	Scheme	2	seems	to	be	the	most	
plausible	pathway	for	the	formation	of	compound	10a	from	the	
reaction	 of	 compound	4a	 with	 compound	5a	 or	 nitrile	 imine	
6a,	which	was	prepared	 in	situ	by	 treatment	of	compound	5a	
with	 triethylamine,	 the	 reaction	 involves	 the	 initial	 formation	
of	 thiohydrazonate	 7a,	 which	 undergoes	 intermolecular	
cyclization	as	soon	as	it	is	formed	to	yield	the	intermediate	8a	
or	via	1,3‐dipolar	cycloaddition	of	nitrilimine	6a	to	C=S	double	
bond	of	4a	to	give	final	product	compound	10a	via	elimination	
of	hydrogen	sulphide.		

Analogously,	 the	 appropriate	 hydrazonoyl	 halides	 5b‐e	
reacted	 with	 the	 appropriate	 4a‐c	 in	 boiling	 chloroform	 in	
presence	of	catalytical	amount	of	triethylamine	gave	compound	
10b‐e,	11a‐e	and	12a‐d,	respectively	(Scheme	2).	

Also,	 reaction	 of	 compound	 1	 with	 1,3‐diphenyl‐1H‐
pyrazole‐4‐carbaldehyde	 (14)	 in	 methanol	 containing	 few	
drops	 of	 hydrochloric	 acid	 led	 to	 the	 formation	 of	 10‐(1,3‐
Diphenyl‐1H‐pyrazol‐4‐yl)‐2,7‐dithioxo‐2,3,7,8,9,10‐hexa‐
hydro‐1H,6H‐1,3,6,8,9‐pentaaza‐anthracene‐4,5‐dione	 (15)	
(Scheme	4).	Structure	compound	15	was	confirmed	by	spectral	
data,	 elemental	 analyses	 and	 chemical	 transformation.	 Thus,	
compound	15	 react	 with	 hydrazonoyl	 halides	5a‐c	 in	 boiling	
chloroform	 to	 give	 16a‐c,	 respectively.	 1H	 NMR	 spectrum	 of	
compound	16b	 showed	 signals	 at	 1.07	 (t,	 3H,	 J	 =	 7	 Hz,	 CH3),	
4.40	(q,	2H,	J	=	7	Hz	CH2),	6.02	(s,	1H,	CH‐9),	6.88‐8.08	(m,	10H,	
ArH's),	11.27	(s,	1H,	NH)	ppm.		

Moreover,	 reaction	 of	 2,8‐dithioxo‐2,3,7,8,9,10‐hexahydro‐
pyrido[2,3‐d:6,5‐d']dipyrimidine‐4,6(1H,5H)‐dione	 (17)	 [29]	
with	 the	 appropriate	 hydrazonoyl	 halides	 5a‐c	 were	 carried	
out	 in	chloroform	under	reflux	 for	along	 time	gave	compound	
18a‐c	 (Scheme	 4).	 Structures	 18	 were	 inferred	 from	 their	
spectral	 data,	 elemental	 analyses	 and	 alternative	 synthesis.	
Thus	 1H	NMR	 spectrum	of	18b	 showed	 signals	 at	 δ	 =	1.14	 (t,	
6H,	J	=	7	Hz,	2CH3),	3.56	(s,	2H,	CH2),	4.13	(q,	4H,	J	=	7	Hz,	2CH2),	
6.99‐7.35	 (m,	 10H,	 ArH's),	 10.8	 (s,	 1H,	 NH).	 Its	 IR	 spectrum	
revealed	bands	at	3386	(NH)	1747	(CO	ester),	1681	(CO),	1600	
(C=C).	 Thus,	 compound	 13b	 reacted	 with	 formaldehyde	 in	
presence	 of	 hydrochloric	 acid	 gave	 product	 identical	 in	 all	
aspect	(M.p.,	mixed	m.p.,	and	spectra)	with	compound	18b.	



460	 Abdel‐Aziem	et	al.	/	European	Journal	of	Chemistry	3	(4)	(2012)	455‐460	
	
3.2.	Antimicrobial	activity	
	

The	 tested	 microorganisms	 were	 Gram‐positive	 bacteria:	
Staphylococcus	 Aureus	 (ATCC	 25923)	 and	 Bacillus	 Subtilis	
(ATCC	6635),	Gram‐negative	bacteria:	Salmonella	typhimurium	
(ATCC	 14028)	 and	 Escherichia	 coli	 (ATCC	 25922),	 Fungus:	
Candida	Albicans	(ATCC	10231)	and	Aspergillus	fumigatus.	

In	 general,	 (for	 high	 and	 low	 concentrations)	 compounds	
4a‐c,	12a	 and	18b	were	capable	 low	 inhibition	against	Gram‐
positive	bacteria	Bacillus	Subtilis	and	compounds	10b	and	11a	
were	 capable	 intermediate	 inhibition	 against	 Gram‐negative	
bacteria	 Escherichia	 coli	 whereas	 compound	 4a	 show	
intermediate	 inhibition	 against	 yeast	 and	 fungi	 (Table	 1).	
Staphylococcus	 Aureus	 (ATCC	 25923)	 and	 Salmonella	
typhimurium	 (ATCC	 14028)	 are	 no	 effect	 for	 all	 synthesized	
compounds.	
	
4.	Conclusion	
	

The	 present	 work	 describes	 the	 study	 of	 reactions	 of	
hydrazonoyl	 halides	 towards	 some	 pyridodipyrimidinethione	
derivatives	 to	 give	 pyridotriazolopyrimidines	 derivatives	 in	 a	
good	yield	with	some	biological	activity.	
	
References	
	
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1988,	48,	91‐101.		
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