Synthesis and antimicrobial activity of a novel series of condensed thienopyrimidines

Abstract

Alkylation of 2-thioxo-5,6,7,8-tetrahydrobenzothieno[2,3-d]
pyrimidin-4(3)-one (2) gave the -alkylating products 3-5.
Reaction of 3-carboxamide 1 with terphthaloyl, isophthaloyl
chloride and benzoin afforded bisthienopyrimidines 6, 7 and pyrrolopyrimidineone 9, respectively. Condensation of 1 with aromatic aldehydes afforded compounds 11ac. Alkylation of compounds 11a–c with allyl bromide resulted in -alkyl thienopyrimidine derivatives 12a–c.
Alkylation of 11a,b with 4-bromobutyl acetate gave
butylacetate derivatives 13a,b. which were deacetylated
to provide 14a,b. All the newly synthesized compounds
were characterized by the IR, 1H, 13C NMR and elemental
analyses. Selected members of these compounds were
screened for antimicrobial activity.