Catalyst-free synthesis of highly functionalized triazole hexahydroquinoline carbohydrazide scaffolds via four-component cyclocondensation reaction

Abstract

A new class of multi-functional triazole hexahydroquinoline carbohydrazide named 2-amino-7,7-dimethyl-5-oxo-4-phenyl-1-(4H-1,2,4-triazol-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carbohydrazide has been synthesized by a novel multi-component process involving the reaction of dimedone, 3-amino-1,2,4-triazole, various benzaldehyde with cyanoacetohydrazide under mild conditions in the stoichiometric melt and chloroform in sequence. The simple one-pot process, straight product isolation without applying tedious purification procedures, progression of the reaction without using any catalyst, the application of diverse aldehydes causing a high molecular diversity, the existence of several nitrogen atoms in the product structure, and the possibility of creating multiple hydrogen bonding in the final compound are attractive specifications of the present strategy.

Keywords: Catalyst-free approach; Cyanoacetohydrazide; Four-component reaction; Hexahydroquinoline carbohydrazide; Triazole.