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

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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… Click to show full 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.

Keywords: sulfoxonium ylides; sulfoxonium; cyclization; acetate derivatives; pyridin acetate; indolizine synthesis

Journal Title: Organic chemistry frontiers
Year Published: 2021

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