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

Khan, Musharraf, Pitard, Arnaud, O'Gorman, P.A. and Hemming, Karl (2013) 1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-azetines as thiocyanate equivalents. Tetrahedron, 69 (4). pp. 1279-1284. ISSN 0040-4020

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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.

Item Type: Article
Uncontrolled Keywords: Azetine, Nitrile oxide, "1,2,4-Oxadiazole", Cycloreversion, Azide, "1,2,3-Triazole"
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
Related URLs:
Depositing User: Karl Hemming
Date Deposited: 02 Jan 2013 13:43
Last Modified: 03 Dec 2016 09:34
URI: http://eprints.hud.ac.uk/id/eprint/16411

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