Issue 9, 2024

Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines

Abstract

Herein, we report a metal-free, scalable, and cascade protocol for constructing polysubstituted pyridines from N,N-dimethyl enaminones and α,β-unsaturated sulfonylketimines by cleaving C–N/N–S bonds. This efficient methodology (up to 96% yield) assembles multi-substituted pyridines, including those containing pharmacologically important cores, via cycloaddition rather than a radical pathway. Significantly, this is a rare example of rapidly forming polysubstituted pyridines under metal-free conditions through C–N/N–S bond cleavage of tertiary enaminones.

Graphical abstract: Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines

Supplementary files

Article information

Article type
Research Article
Submitted
04 Dec 2023
Accepted
08 Mar 2024
First published
10 Mar 2024

Org. Chem. Front., 2024,11, 2607-2612

Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines

X. Li, Q. Pang, Y. Zhang, Y. Li, Q. Yang, X. Lin, X. Xie and W. Huang, Org. Chem. Front., 2024, 11, 2607 DOI: 10.1039/D3QO02001K

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