Utility of 3-Aroylprop-2-enoic acid in Heterocyclic Synthesis

Abstract

3-Aroylprop-2-enoic acid derivative (1) reacted with 1,2-diaminobenzene, 2,3-diaminopyridine, and 4-quinazolinone to give the adducts (3, 4) and (6), respectively. Treatment of (6) with hydroxylamine gave the adducts (8). The Michael addition of chromone derivative, ethyl cyanoacetate, malononitrile, 3,5-dimethylpyrazole and 3-methyl pyrazolin-5-one to (1) yielded the adducts (10-12), (14-16), (19) and (20). Reacting (19) and (20) with hydroxylamine gave (21) as an isomeric mixture and (22), respectively. Treatment of (19) and (20) with hydrazine hydrate afforded (26) and (25) as a tautomeric mixture, respectively. Structures of all new compounds are evidenced by microanalytical and spectral data.