An Efficient Solvent-Free Microwave-Assisted Synthesis of Cinnamamides by Amidation Reaction Using Phenylboronic Acid/Lewis Base Co-catalytic System

Abstract

A microwave-assisted dehydrative amide condensation reaction is reported as an efficient access to cinnamamide derivatives under solvent-free conditions. This protocol between conjugated carboxylic acids and amines is based on the use of a co-catalytic system, including the presence of the commercially available phenylboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO), with a complete chemoselectivity in favor of the corresponding α,β-unsaturated amides. The implementation of the reaction needs no special precaution, and less reactive amines, such as substituted anilines, are also efficient under these conditions. A series of novel conjugated amides have been evaluated for their cytotoxic activities against several human cancer cell lines.

Key words

cinnamamide derivatives - direct amide formation - boronic acid - microwave heating - catalytic system

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