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Updated: Jul 7, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Breaking Azacalix[4]arenes into Induline Derivatives
Zhongrui Chen1, Gabriel Canard1, Olivier Grauby1
1Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), UMR 7325 CNRS Aix-Marseille Université, Campus de Luminy, Case 913, F-13288 Marseille, France.
Abstract:
Tetraamino-tetranitro-azacalixarene 5 is at the crossroad of two different families of compounds depending on the conditions and the agent used to reduce the NO2 groups: (1) azacalixphyrin 7 in neutral medium, or (2) phenazinium of type 8 in acidic medium. The key role of the N-substituted amino functions at the periphery is highlighted by investigating octaaminoazacalixarene as a model compound, and by using the corresponding tetrahydroxy-tetranitro-azacalixarene 15 as a precursor, which behaves differently.
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