1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-Azetines as thiocyanate equivalents

Karl Hemming, Musharraf N. Khan, Paul A. O'Gorman, Arnaud Pitard

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1- azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences.

Original languageEnglish
Pages (from-to)1279-1284
Number of pages6
JournalTetrahedron
Volume69
Issue number4
Early online date7 Dec 2012
DOIs
Publication statusPublished - 28 Jan 2013

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