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Paper | Regular issue | Vol 75, No. 12, 2008, pp.2937-2948
Published online, 10th July, 2008
DOI: 10.3987/COM-08-11426
Synthesis and Antimicrobial Evaluation of Some Bis(thioxopyridine), Bis(pyrazolo[3,4-b]pyridine), Bis(thieno[2,3-b]pyridine), Bis(1,3,4-Thiadiazole) and Bisthiophene Derivatives

Nabila A. Kheder, Yahia N. Mabkhot, and Ahmad M. Farag*

*Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt


Condensation of the N,N’-(ethane-1,2-diyl)bis(cyanoacetamide) (1) with aromatic aldehydes gave the corresponding N,N’-ethane-1,2-diyl)- bis(2-cyano- 3-phenylacrylamide) derivatives 2a-c. The latter products react with 2-cyanothioacetamide to afford 1,2-bis(4-aryl-3,5-dicyano-6-mercapto-2-oxo-1,2- dihydropyridin-1-yl)ethane derivatives 5a-c. Treatment of 1,2-bis(3,5-dicyano- 6-mercapto-2-oxo-4-phenyl-1,2-dihydropyridin-1-yl)ethane (5a) or its S-methyl derivative 6 with hydrazine hydrate afforded 1,2-bis(3-amino-5-cyano-6,7- dihydro-7-methyl-6-oxo-4-phenyl-1H-pyrazolo[3,4-b]pyridin-1-yl)ethane (7). Reaction of bis(6-mercaptopyridine) 5b with chloroacetone gave the 1,2- bis[2-acetyl-3-amino-6,7-dihydro-5-cyano-4-(4-methoxyphenyl)-6-oxothieno[2,3-b]pyridine-7-yl]ethane (9). Treatment of the bis(cyanoacetamide) 1 with phenyl isothiocyanate afforded N,N’-(ethane-1,2-diyl)bis[2-cyano-3-mercapto-3-(phenyl amino)acrylamide] (11) which reacts with hydrazonoyl halides 12a,b or haloketones 15a-c to give the corresponding N,N’-(ethane-1,2-diyl)bis[2-cyano- 2-(3,5-disubstituted-2(3H)-1,3,4-thiadiazolylidene)acetamides] 14a,b or N,N’-(ethane-1,2-diyl)bis[4-amino-5-substituted-2-(phenylamino)thiophene-3-carboxamide] 16a-c derivatives, respectively. Antimicrobial evaluation of selected example of the newly synthesized compounds was carried out.