Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines

  1. Yelong Lei and
  2. Jiaxi XuORCID Logo

Submitting author affiliation: Beijing University of Chemical Technology, Beijing, China

Beilstein Arch. 2021, 202179. https://doi.org/10.3762/bxiv.2021.79.v1

Published 16 Nov 2021

  • Preprint

Abstract

Alkyl 2-diazo-3-oxoalkanoates generate alkoxycarbonylketenes, which undergo an electrophilic ring expansion with aziridines to afford alkyl 2-(oxazolin-2-yl)alkanoates in good to excellent yields under microwave irradiation. The method can be also applied in the synthesis of 2-(oxazolin-2-yl)alkanamides and 1-(oxazolin-2-yl)alkylphosphonates.

Keywords: aziridine; diazooxoester; diazo compound; ketene; oxazoline; ring expansion

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Lei, Y.; Xu, J. Beilstein Arch. 2021, 202179. doi:10.3762/bxiv.2021.79.v1

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