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Synthesis 2017; 49(19): 4478-4488
DOI: 10.1055/s-0036-1590822
DOI: 10.1055/s-0036-1590822
paper
Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2H-azirines
We gratefully acknowledge the financial support of the Russian Science Foundation (Grant No. 17-13-01078). This research used resources of the ‘Magnetic Resonance Research Centre’, the ‘Chemical Analysis and Materials Research Centre’, the ‘Centre for X-ray Diffraction Studies’ and the ‘Chemistry Educational Centre’ of the Research Park of St. Petersburg State University.Further Information
Publication History
Received: 17 May 2017
Accepted after revision: 03 June 2017
Publication Date:
03 August 2017 (online)
Abstract
A convenient gram-scale method for the preparation of 2-halo-2H-azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh2(Piv)4, while FeCl2·4H2O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.
Key words
azirines - isoxazoles - haloheterocycles - rhodium(II) carboxylates - iron(II) chloride - catalysis - isomerizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590822.
- Supporting Information
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For recent reviews on 2H-azirine chemistry, see: