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Synthesis 2013; 45(2): 260-264
DOI: 10.1055/s-0032-1317947
DOI: 10.1055/s-0032-1317947
paper
Mononuclear Heterocyclic Rearrangement of 5-Arylisoxazole-3-hydroxamic Acids into 3,4-Substituted 1,2,5-Oxadiazoles
Further Information
Publication History
Received: 15 October 2012
Accepted after revision: 05 December 2012
Publication Date:
18 December 2012 (online)
Abstract
By a series of successive transformations, 5-arylisoxazole-3-carboxylic acids (aryl = phenyl, p-tolyl, 2,5-dimethylphenyl) have been converted into 5-arylisoxazole-3-hydroxamic acids, which undergo rearrangement by the action of aqueous KOH to form 3,4-substituted 1,2,5-oxadiazoles. The structure of one of them, 1-(2,5-dimethylphenyl)-2-(4-hydroxy-1,2,5-oxadiazol-3-yl)ethanone, has been confirmed by single crystal X-ray analysis.
Key words
isoxazoles - 1,2,5-oxadiazoles - furazans - rearrangement - crystal structure - hydroxamic acidsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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