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Updated: Apr 26, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
[3 + 3]-cycloaddition reactions of α-acidic isocyanides with 1,3-dipolar azomethine imines
Juan Du1, Xianxiu Xu, Yifei Li
1Department of Chemistry, Northeast Normal University , Changchun 130024, China.
Abstract:
α-Acidic isocyanides are versatile reagents in organic synthesis, especially for the synthesis of five-membered heterocycles via [3 + 2]-cycloaddition reactions with activated multiple bonds. In this communication, the first [3 + 3]-cross-cycloaddition of α-acidic isocyanides with 1,3-dipolar azomethine imines to generate a series of 1,2,4-triazine derivatives with significant regiochemical control under mild catalytic reaction conditions is described. This new strategy shows that α-acidic isocyanides can also be taken as potent reagents for the synthesis of six-membered heterocycles through [3 + 3]-cross-cycloaddition reactions with 1,3-dipoles.
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