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Updated: Dec 28, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Direct access to vicinally functionalized and N-trifluoroacetylated (bicyclic)ketopiperazines using a readily
Antonio Moreno1, Timothy K Beng1
1Department of Chemistry, Central Washington University, Ellensburg, WA 98926, USA. Timothy.beng@cwu.edu.
Abstract:
Functionalized 2-piperazinones play essential roles as conformationally-constrained peptidomimetics by mimicking inverse γ-turns in peptides. Here, we describe an efficient, scalable, stereoselective, modular, and chemoselective annulation protocol between a novel N-trifluoroacetyl anhydride and several reactive partners, including lactim ethers, imidoyl chlorides, aryl aldimines, and 1,3-azadienes, leading to vicinally functionalized (bicyclic) 2-piperazinones.
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