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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 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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-02359980
Contributor : Laurent Jonchère <>
Submitted on : Tuesday, November 12, 2019 - 4:00:03 PM
Last modification on : Wednesday, January 29, 2020 - 1:22:02 AM

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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, Georg Thieme Verlag, 2019, 51 (20), pp.3891-3900. ⟨10.1055/s-0039-1690132⟩. ⟨hal-02359980⟩

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