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Updated: Feb 22, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
(4+3) Cycloaddition Reactions of N-Alkyl Oxidopyridinium Ions
Chencheng Fu1, Nestor Lora1, Patrick L Kirchhoefer1
1Department of Chemistry, University of Missouri-Columbia, Columbia, MO, 65211, USA.
Abstract:
N-Methylation of methyl 5-hydroxynicotinate followed by reaction with a diene in the presence of triethylamine afforded (4+3) cycloadducts in good to excellent yields. High regioselectivity was observed with 1-substituted and 1,2-disubstituted butadienes. Density functional theory calculations indicate that the cycloaddition involves concerted addition of the diene onto the oxidopyridinium ion. The process provides rapid access to bicyclic nitrogenous structures resembling natural alkaloids.
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