Synthesis and biological activity of carbamates derived from ethyl 1-[(phenylcarbonyl)amino]naphtho[2,1-b]furan-2-carboxylate

M. R. Hema, M. Ramaiaha, V. P.

Abstract

Ethyl 3-aminonaphtho[2,1-b]furan-2-carboxylate (1) on benzoylation, produced ethyl1- [(phenylcarbonyl)amino] naphtho[2,1-b]furan-2-carboxylate (2). Treatment of ester (2) with hydrazine hydrate gave N-[2- (hydrazilylcarbonyl)naphtho[2,1-b]furan-1-yl]benzamide (3), which on diazotization resulted in the formation of 1- [(phenylcarbonyl )amino] naphtho [2,1-b]furan-2-carbonyl azide (4). The azide (4) on Curtius rearrangement with alcohols and phenols afforded the corresponding carbamates,(5a-g). The structures of newly synthesized carbamates were confirmed by spectral and analytical data and were screened for their antimicrobial activity by agar diffusion method. Some of the carbamates were found to possess better antibacterial activity against bacteria V. cholerae and E. coli.