Synthesis and antibacterial activity of 2-{[3-phenyl-7-substituted-2-(phenylimino)-2,3-dihydro[1,3]thiazoIo[4,5-d]pyrimidin-5-yl]imino}-3-ethoxyphthalimido-1,3-thiazolidin-4-one

摘要

In the present investigation, desired fused ring system 2-{[3-phenyl-7-substituted-2-(phenylimino)-2,3-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl]imino}-3-ethoxyphthalimido-1,3-thiazolidin-4-one-(6a-e) have been described. N,N'-Diphenylthiourea is converted to 3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one (1) by the reaction with chloroacetic acid and sodium acetate in acetic acid. This on Claisen condensation with various aromatic aldehydes gave corresponding 5-arylidene derivatives (2a-c). These are treated with guanidine nitrate to furnish 2-aminopyrimidine derivatives (3a-e). These when reacted with ammonium thiocyanate in dilute HCl, 1-[3-phenyl-7-substituted-2-(phenylimino)-2,3-dihydro[1,3]thiazoIo[4,5-d]pyrimidin-5-yl]thiourca (4a-e) are yielded. These compounds are converted to corresponding thiazolidinone derivatives (5a-e) by cyclisation with chloroacetic acid and sodium acetate. Subsequent condensation of 5a-c with bromoethoxyphthalimide gave the title compounds 6a-c. The structures of synthesized compounds have been confirmed by spectral and analytical studies. Six compounds have been studied for antibacterial activity which show moderate to weaker activity.