1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-azetines as thiocyanate equivalents |
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Authors: | Karl Hemming Musharraf N Khan Paul A O'Gorman Arnaud Pitard |
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Institution: | Institute for Materials, Medicines and Molecular Sciences, Division of Chemistry, School of Applied Sciences, University of Huddersfield, West Yorkshire, HD1 3DH, United Kingdom |
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Abstract: | 1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1-azetines gave a series of oxadiazabicyclo3.2.0]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. |
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