Tetrahedron

Cycloadditions of nitrile oxides to amidoximes. A general synthesis of 3, 5-disubstituted 1, 2, 4-oxadiazole-4-oxides.

P Quadrelli, AG Invernizzi, M Falzoni, P Caramella

Index: Quadrelli, Paolo; Invernizzi, Anna Gamba; Falzoni, Mario; Caramella, Pierluigi Tetrahedron, 1997 , vol. 53, # 5 p. 1787 - 1796

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Citation Number: 27

Abstract

The cycloaddition of nitrile oxides to amidoximes is a general method for the sinthesis of 3, 5- disubstituted 1, 2, 4-oxadiazole-4-oxides with the same or different substituents. The yields are only moderate since an equivalent amount of the nitrile oxide is consumed by reaction with the amine released in the fragmentation of the primary cycloadducts and reforms the amidoxime. With excess nitrile oxides the 1, 2, 4-oxadiazole-4-oxides undergo a ...

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