M. Gad-Elkareem, Abu-Bakr A. El-Adasy
Jan 29, 2010
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Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
Ethyl 5-cyano-6-mercaptonicotinate derivatives 1a,b reacted with the N-[4-(aminosulfonyl) phenyl]-2-chloroacetamide derivatives 2a,b to give the ethyl 6-[(2-{[4-(aminosulfonyl) phenyl]amino}-2-oxoethyl)thio]nicotinate derivatives 3a–d. Cyclization of 3a–d afforded the corresponding ethyl 3-amino-2-({[4-(aminosulfonyl)phenyl]amino}carbonylthieno[2,3-b] pyridine-5-carboxylate derivatives 4a–d. Ethyl 3-[4-(amino-sulfonyl)phenyl]-4-oxopyrido [3′,2′:4,5]thieno[3,2-d]pyrimidine-8-carboxylate derivatives 5a–d and ethyl 3-[4-(amino- sulfonyl)phenyl]-4-oxopyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]-triazine-8-carboxylate derivat- ives 6a–d were prepared from 4a–d. Reaction of 1a,b with chloroacetonitrile (7) and condensation of the thus formed 3-aminothienopyridines 8a,b with dimethylformamide-dimethylacetal (DMF-DMA) yielded the corresponding ethyl 2-cyano-3-{[(N, N-dimethylamino)methylene]amino}thieno[2,3-b]pyridine-5-carboxylate derivatives 9a,b. Reaction of compounds 9a,b with the sulfadiazine (10) gave ethyl 4-{[4-(amino- sulfonyl)phenyl]amino}pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine-8-carboxylate derivatives 12a,b. Antibacterial activity was screened for some of the newly synthesized compounds. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.