An Efficient Solvent-Free Microwave-Assisted Synthesis of Cinnamamides by Amidation Reaction Using Phenylboronic Acid/Lewis Base Co-catalytic System - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2019

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

Résumé

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 alpha,beta-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.

Domaines

Chimie
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Dates et versions

hal-02359980 , version 1 (12-11-2019)

Identifiants

Citer

Khadidja Khaldoun, Abdelmounaim Safer, Salima Saidi-Besbes, Bertrand Carboni, Remy Le Guevel, et al.. An Efficient Solvent-Free Microwave-Assisted Synthesis of Cinnamamides by Amidation Reaction Using Phenylboronic Acid/Lewis Base Co-catalytic System. Synthesis: Journal of Synthetic Organic Chemistry, 2019, 51 (20), pp.3891-3900. ⟨10.1055/s-0039-1690132⟩. ⟨hal-02359980⟩
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