Reaction between 2,2′-dithiodianiline and activated alkynes. Synthesis of 4H-1,4-benzothiazines

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Abstract
By the title reaction acetylenic esters (2a–c), ketones (2d–g), and the nitrile (2h) gave in all cases the corresponding 4H-1,4-benzothiazines (3) together with other products whose nature depends on the alkyne used. Thus benzothiazoline and/or benzothiazole, benzothiazepine, and vinylsulphides were obtained in the representative cases (2c, f, h) studied in detail. Some of these latter compounds have been independently synthesised by reaction of 2-aminobenzenethiol with corresponding alkyne (2). In particular conditions by the reactions between 2,2′-dithiodianiline (1) and alkynes (2f, d) we isolated bisenamine compounds (19) and (20) respectively and their intermediacy in formation of the corresponding benzothiazines (3f) and (3d) was achieved. The mechanisms of the observed reactions are also suggested.

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