Tetrahedron

Microwave-induced generation and reactions of nitrile sulfides: an improved method for the synthesis of isothiazoles and 1, 2, 4-thiadiazoles

EAF Fordyce, AJ Morrison, RD Sharp, RM Paton

Index: Fordyce, Euan A.F.; Morrison, Angus J.; Sharp, Robert D.; Paton, R. Michael Tetrahedron, 2010 , vol. 66, # 35 p. 7192 - 7197

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Citation Number: 13

Abstract

The 1, 3-dipolar cycloaddition reactions of nitrile sulfides, generated by microwave-assisted decarboxylation of 1, 3, 4-oxathiazol-2-ones, have been investigated. By this approach ethyl 1, 2, 4-thiadiazole-5-carboxylates 3 were prepared in good yield by cycloaddition of the nitrile sulfides to ethyl cyanoformate. Similarly, reaction of benzonitrile sulfide with dimethyl acetylenedicarboxylate (DMAD) afforded dimethyl 3-phenylisothiazole-4, 5-dicarboxylate ( ...