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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Hexafluoroantimonic acid catalysis: formal [3+2+2] cycloaddition of aziridines with two alkynes
Ming-Bo Zhou1, Ren-Jie Song, Jin-Heng Li
1State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
Abstract:
A practical method for the synthesis of azepine derivatives, a typical seven-membered heterocyclic ring system, was developed and involves the use of hexafluoroantimonic acid to catalyze a formal [3+2+2] cycloaddition of aziridines with two alkynes. This method was applicable to two of the same or different terminal alkynes for the [3+2+2] cycloaddition with unactivated aziridines, and furnished the corresponding azepine derivatives in good yields with good levels of chemo- and regioselectivity. The mechanism was also discussed according to the results of the in situ HRMS and (1)H NMR analysis.
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