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N-Heterocyclic carbene (NHC)-catalyzed tandem imine umpolung–aza-Michael addition–oxidation of β-carboline cyclic imines

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Abstract

Herein we describe an NHC-catalyzed umpolung of β-carboline-based cyclic imines for their conversion to the corresponding N-substituted cyclic amides. The key to the success of this transformation appears to be that NHC upon reaction with the imine concomitantly goes through the generation of an aza-Breslow intermediate and aza-Michael addition followed by oxidation with molecular oxygen to deliver the N-substituted amide products. The developed method has enabled the synthesis of various biologically relevant β-carboline-1-one derivatives in good yields.

Graphical abstract: N-Heterocyclic carbene (NHC)-catalyzed tandem imine umpolung–aza-Michael addition–oxidation of β-carboline cyclic imines

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Article information


Submitted
13 Jan 2020
Accepted
23 Jan 2020
First published
23 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

N-Heterocyclic carbene (NHC)-catalyzed tandem imine umpolung–aza-Michael addition–oxidation of β-carboline cyclic imines

K. Satyam, B. Harish, J. B. Nanubolu and S. Suresh, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00321B

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