Cycloaddition reactions of nitrile sulfides with acetylenic esters. Synthesis of isothiazolecarboxylates

RK Howe, TA Gruner, LG Carter…

Index: Howe,R.K. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 3736 - 3742

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Citation Number: 50

Abstract

Ehidence is reported for production of nitrile sulfides as reactive intermediates in the thermolysis of 1, 3, 4-oxathi-azol-2-ones. The nitrile sulfides were trapped with dimethyl acetylenedicarboxylate to give good yields of dimethyl 3-sribstituted-4, 5- isothiazoledicarboxylates 6a-t. The diacids 7a-r were readily converted to 3-substituted-4- isothiazolecarboxylic acids Sa-r by thermal decarboxylation. 3-Aryl-4- ...