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Communication | Special issue | Vol 5, No. 1, 1976, pp.261-266
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0261
Stereochemistry of Nonoxidative Photocyclization of Indole-2-carboxanilides to an Indolo[2,3-c]quinoline System

Yuichi Kanaoka,* Sadao Nakao, and Yasumaru Hatanaka

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan


Nonoxidative photocyclization of indole-2-carboxanilides (1a and 1b) yielded mainly the 6a-11b cis isomers of indolo[2,3-c]quinolin-6-one 5. By contrast, from the N-methyl homologs (1c and 1d) only the trans isomers 4 were obtained. The mechanism was explained in terms of the dual pathways involving a sigmatropic 1,5-hydrogen shift and a competing “solvent-mediated” course.