Conversion of imino-1, 2, 3-dithiazoles into 2-cyanobenzothiazoles, cyanoimidoyl chlorides and diatomic sulfur

RF English, OA Rakitin, CW Rees…

Index: English, Russell F.; Rakitin, Oleg A.; Rees, Charles W.; Vlasova, Olga G. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 3 p. 201 - 205

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Citation Number: 48

Abstract

Primary aromatic amines condense with 4, 5-dichloro-1, 2, 3-dithiazolium chloride 1 to give high yields of the N-aryl imines 2 which on heating give 2-cyanobenzothiazoles 3, thus providing a simple two-step route to these heterocycles from the appropriate aniline. This thermolysis is favoured by electron donating substituents in the aniline ring, and retarded by electron withdrawing groups in favour of a second pathway in which both dithiazole sulfur ...