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

TETRAHEDRON

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Article

Hemming, Karl¹  Khan, Musharraf N.¹  O'Gorman, Paul A.¹  Pitard, Arnaud¹ 

[1] Univ Huddersfield, Sch Appl Sci, Div Chem, Inst Mat Med & Mol Sci, Huddersfield HD1 3DH, W Yorkshire, England

关键词: Azetine;    Nitrile oxide;    1,2,4-Oxadiazole;    Cycloreversion;    Azide;    1,2,3-Triazole;   

DOI  :  10.1016/j.tet.2012.12.007

来源: Elsevier

【 摘 要 】

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. (c) 2012 Elsevier Ltd. All rights reserved.

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