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Communication | Regular issue | Vol 16, No. 10, 1981, pp.1705-1712
Published online, 1st January, 1970
DOI: 10.3987/R-1981-10-1705
2-Methylene-3-phenacylbenzothiazoline: Dimerization and Reactions with Electron-deficient Acetylenes and Olefins

Otohiko Tsuge,* Minoru Tanaka, Hiroshi Simoharada, and Michihiko Noguchi

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


On treatment with triethylamine in acetonitrile at 0°C, 2-methy-3-phenacylbenzothiazolium bromide gave a dimer of 2-methylene-3-phenacylbenzothiazoline in a quantitative yield. The methylene base, generated in situ, reacted with electron-deficient acetylenes and olefins to give 3-substituted 2-phenylpyrrolo[2,1-b]benzothiazole via a Michael type adduct; in some cases Michael type adducts were isolated. On the other hand, the methylene base reacted with tetracyanoethylene to give 2-butadienylidenebenzothiazoline derivative, which on heating in acetic anhydride afforded 1-benzoyl-2-cyanopyrrolo[2,1-b]benzothiazole with the elimination of malononitrile.