Synthesis and antibacterial activity of some novel triazolothienopyrimidines

Abstract

A novel series of some novel 5-substituted-1,2,4-triazolo[4,3-c]8,9,10- trihydrocyclopenta/8,9,10,11,12-pentahydrocyclohepta[ b]thieno[3,2-e]pyrimidin- 3-thiones has been synthesized. The intermediates 4-chloro-2-substituted-5,6,7- trihydrocyclopenta/5,6,7,8,9-pentahydrocyclohepta[b]thieno[2,3-d]pyrimidines were prepared by warming 2-substituted-5,6,7-trihydrocyclopenta/5,6,7,8,9- pentahydrocyclohepta[b]thieno[2,3-d]pyrimidin-4[3H]-ones with oxalyl chloride. Thieno[2,3-d]pyrimidin-4[3H]-ones were prepared by a novel, microwave assisted, solvent free, synthetic route under basic conditions hitherto unreported in the literature from ortho amino ester of thiophene. The chloro derivatives, without further purification, were hydrazinated to yield 2-substituted-4-hydrazino-5,6, 7-trihydrocyclopenta/5,6,7,8,9-pentahydrocyclohepta[b]thieno[2,3-d]pyrimidines. These compounds were cyclized with carbon disulphide to give the title compounds in quantitative yields. The final compounds were screened for antibacterial activity by Kirby Bauer's method using ampicillin as the standard against various gram positive and gram negative bacteria. All the compounds showed antibacterial activity comparable with the standard. © 2007 Pharmaceutical Society of Japan.