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Updated: Aug 6, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis and cross-coupling reactions of 7-azaindoles via a new donor-acceptor cyclopropane
Xiaomei Zheng1, Michael A Kerr
1Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Abstract:
[reaction: see text] A new type of donor-acceptor cyclopropane has been prepared from commercially available cyclopropane-1,1-diesters. This cyclopropane reacts with triflic anhydride to produce an isolable tristrifloxy intermediate which when treated with primary amines gives 6-trifloxy-7-azaindolines which in turn can be dehydrogenated to the azaindoles. The 6-trifloxy substituent can be used to introduce diversity at this position via a variety of cross-coupling reactions thus preparing potentially interesting compounds based on the important 7-azaindole pharmacophore.
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