Tetrahedron

Iodine-mediated cyclisation of thiobenzamides to produce benzothiazoles and benzoxazoles

NK Downer-Riley, YA Jackson

Index: Downer-Riley, Nadale K.; Jackson, Yvette A. Tetrahedron, 2007 , vol. 63, # 41 p. 10276 - 10281

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Citation Number: 33

Abstract

Iodine, which is available as a crystalline solid, is easier to handle and less toxic than liquid bromine. The ability of iodine to act as an oxidant as well as a Lewis acid has been exploited in the cyclisation of thiols and disulfides to produce benzothiophenes, dihydronaphthothiophenes, dihydronaphthopyrans and thiazinones. 6, 7 and 8 The use of iodine in cyclisation of thiobenzamides to benzothiazoles, however, has not been reported. We ...