Synthesis and Antibacterial Activity of N-Substituted 2-(Benzylimino)-4-styryl-2,5-dihydrofuran-3-carboxamides

Previously unknown N-substituted 2-(benzylimino)-4-styryl-2,5-dihydrofuran-3-carboxamides were synthesized by reaction of 2-imino-2,5-dihydrofuran-3-carboxamides with benzylamine in glacial acetic acid. It was found that a part of benzylamine reacts as a nucleophile at the imino group and that the other part undergoes oxidation followed by dehydration to generate benzylimine which acts as a synthetic equivalent of benzaldehyde toward the 4-methyl group. The synthesized compounds were characterized by IR and NMR spectra and elemental analyses. 2-(Benzylimino)-N,5,5-trimethyl-4-(2-phenylethenyl)-2,5-dihydrofuran-3-carboxamide was also synthesized independently by reaction of previously reported 2-imino-4-(2-phenylethenyl)-N,5,5-trimethyl-2,5-dihydrofuran-3-carboxamide with benzylamine in glacial acetic acid.