Oxidative Cascade Reaction of N-Aryl-3-alkylideneazetidines and Carboxylic Acids: Access to Fused Pyridines

Wangshui Cai, Shuang Wang, Hitesh B. Jalani, Junxian Wu, Hongjian Lu, Guigen Li

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

A versatile silver-promoted oxidative cascade reaction of N-aryl-3-alkylideneazetidines with carboxylic acids is reported, providing a very efficient pathway to functionalized fused pyridines. This method allows introduction of fused pyridine ring systems to heterocycles, drugs, and natural products. A mechanistic study revealed that silver salt is essential for the chemo- and regioselective ring expansion, sequential oxidative nucleophilic additions, and oxidative aromatization. This approach represents the first example of the strained N-heterocycles undergoing a cascade reaction with a π bond and a nucleophile together.

Original languageEnglish
Pages (from-to)3833-3837
Number of pages5
JournalOrganic Letters
Volume20
Issue number13
DOIs
StatePublished - Jul 6 2018

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