Issue 15, 2021

Indolizine synthesis via radical cyclization and demethylation of sulfoxonium ylides and 2-(pyridin-2-yl)acetate derivatives

Abstract

A novel radical cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and sulfoxonium ylides is developed, which provides a straightforward access to structurally diverse methylthio-substituted indolizine. A series of 1,2,3-trisubstituted indolizines are readily synthesized in modest yields. In this process, sulfoxonium ylides undergo disproportionation and produce a type of indolizine derivative which has not been seen before. This route reveals a novel discovery that DMSO does not drop off from sulfoxonium ylides.

Graphical abstract: Indolizine synthesis via radical cyclization and demethylation of sulfoxonium ylides and 2-(pyridin-2-yl)acetate derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
09 Apr 2021
Accepted
31 May 2021
First published
03 Jun 2021

Org. Chem. Front., 2021,8, 4177-4182

Indolizine synthesis via radical cyclization and demethylation of sulfoxonium ylides and 2-(pyridin-2-yl)acetate derivatives

K. Su, X. Guo, L. Zhu, Y. Liu, Y. Lu and B. Chen, Org. Chem. Front., 2021, 8, 4177 DOI: 10.1039/D1QO00550B

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