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 language | English |
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Pages (from-to) | 3833-3837 |
Number of pages | 5 |
Journal | Organic Letters |
Volume | 20 |
Issue number | 13 |
DOIs | |
State | Published - Jul 6 2018 |