Synthesis 2015; 47(18): 2791-2798
DOI: 10.1055/s-0034-1378737
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Isoxazolines and Isoxazoles Inspired by Fipronil

Daniel K. Miller
Department of Chemistry, Ball State University, Muncie, IN 47306-0445, USA   eMail: resammelson@bsu.edu
,
Christopher A. Bailey
Department of Chemistry, Ball State University, Muncie, IN 47306-0445, USA   eMail: resammelson@bsu.edu
,
Robert E. Sammelson*
Department of Chemistry, Ball State University, Muncie, IN 47306-0445, USA   eMail: resammelson@bsu.edu
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Publikationsverlauf

Received: 24. April 2015

Accepted after revision: 05. Juni 2015

Publikationsdatum:
29. Juli 2015 (online)


Abstract

Phenylpyrazoles (or arylpyrazoles) are known to be extremely potent as noncompetitive inhibitors of the GABA-gated chloride channel on the GABA receptor. This project involves the synthesis of novel isoxazole and isoxazoline heterocycles that have similar structural features to the commercially used phenylpyrazole, fipronil. Synthesis of the appropriately substituted styrenes and phenylacetylenes is followed by 1,3-dipolar cycloaddition reaction with several aliphatic nitrile oxides, which are prepared in situ from aldoximes with bleach. Relative reaction rates were determined for these specialized alkene and alkyne dipolarophiles.

Supporting Information

 
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