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Updated: Apr 15, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of Multisubstituted Diazatricyclic Molecules Via Intramolecular Cycloaddition of Cyclic Azomethine Ylides
Yui Irie1, Kosuke Mizuno1, Nariyoshi Umekubo1
1Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8601, Japan.
Abstract:
Diazatricyclic molecules were synthesized from a 4-hydroxyproline derivative. The hydroxy group was transformed into an amino group, onto which an allyl substituent was introduced. Cross-metathesis enabled further substitution on the allyl moiety. Condensation of the resulting 4-aminoproline derivatives with aldehydes generated azomethine ylides that underwent intramolecular cycloaddition to form the tricyclic framework. Functional groups embedded within the tricyclic framework served as handles for further derivatization.
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