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Communication | Regular issue | Vol 3, No. 10, 1975, pp.805-810
Published online, 1st January, 1970
DOI: 10.3987/R-1975-10-0805
Oxidative Cyclization of Nb-Dimethyltryptamine, 3-Indolepropanol, and 3-Indolepropnethiol with N-Bromo- or N-Chlorosuccinimide

Tohru Hino,* Hidetoshi Miura, Toru Nakamura, Ryoichi Murata, and Masako Nakagawa

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


The reaction of Nb-dimethyltryptomine (5b) with NBS in carbon tetrachloride yielded a quaternary salt of pyrrolo[2,3-b]indole (7b). The similar oxidative cyclization of 3-indolepropanol (5c) and 3-indolepropanethiol (5e) with NBS in methylene chloride gave pyrano- and thiopyranoindoles (7c and 7e). Further halogenation of 7c with NCS yielded a spirooxindole (12, Y=O) and a dichloride (l3), whereas 7e with NBS gave 12 (Y=S) and bromothiopyranoindole (14).