Tetrahedron

Regioselective hydrodehalogenation of 3, 5-dihaloisothiazole-4-carbonitriles: synthesis of 3-haloisothiazole-4-carbonitriles

HA Ioannidou, PA Koutentis

Index: Ioannidou, Heraklidia A.; Koutentis, Panayiotis A. Tetrahedron, 2011 , vol. 67, # 19 p. 3348 - 3354

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Citation Number: 6

Abstract

Abstract 3, 5-Dibromoisothiazole-4-carbonitrile 1 treated with Zn or In dust (5 equiv) and HCO 2 H undergoes regioselective hydrodebromination to give 3-bromoisothiazole-4- carbonitrile 3 in 70–74% yield. Similarly, 5-bromo and iodo 3-chloroisothiazole-4- carbonitriles 8 and 9 give 3-chloroisothiazole-4-carbonitrile 4 in 77 and 85% yields, respectively. Also hydrodeamination of 5-amino-3-chloroisothiazole-4-carbonitrile 7 using ...