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Updated: Jan 2, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Intramolecular azavinyl carbene-triggered rearrangement of furans
Anton S Makarov1, Maxim G Uchuskin1, A Stephen K Hashmi2,3
1Department of Chemistry , Perm State University , Bukireva 15 , 614990 Perm , Russia .
Abstract:
An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in one-pot starting from easily accessible (furan-2-ylmethyl)propargyl amines. An original method for the synthesis of highly functionalized indolizines from the obtained pyridines has been proposed.
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