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Updated: Feb 24, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Ruthenium-Catalyzed Synthesis of 2H-Azirines from Isoxazolinones
Stefan Rieckhoff1, Marvin Titze1, Wolfgang Frey1
1Institut für Organische Chemie, Universität Stuttgart , Pfaffenwaldring 55, D-70569 Stuttgart, Germany.
Abstract:
2H-Azirines are synthetically versatile, highly strained, three-membered heterocycles containing an imino double bond. We report their efficient Ru-catalyzed synthesis using low catalyst loadings under neutral conditions from isoxazolinone substrates, which are readily accessible from β-ketoesters. The azirines were shown to be efficient precursors for functionalized pyridine, indole, dihydropyrrole, and pyrrolidine heterocycles.
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