Tetrahedron Letters

Synthesis of 4, 5-disubstituted-3-trihalomethylisothiazoles

MP Zawistoski, SM Decker, DA Griffith

Index: Zawistoski, Michael P.; Decker, Shannon M.; Griffith, David A. Tetrahedron Letters, 2009 , vol. 50, # 52 p. 7286 - 7287

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Citation Number: 3

Abstract

Herein, we describe the synthesis of 4, 5-disubstituted-3-trihalomethylisothiazoles from trihaloacetonitriles and 2-cyanothioacetamides or 2-ethoxycarbonylthioacetamides. The reactivity of the necessary trihaloacetonitriles has a significant impact on the observed reaction pathways. Reactions with CF3CN require an oxidant to mediate cyclization, while CCl3CN functions as both the reactant and oxidant.