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Communication | Regular issue | Vol 3, No. 7, 1975, pp.553-556
Published online, 1st January, 1970
DOI: 10.3987/R-1975-07-0553
Photochemical Synthesis of Indolo[2,1-a]isoindole Derivatives by the Cyclization of N-(o-Tolyl)phthalimides

Yuichi Kanaoka,* Chieko Nagasawa, Hideo Nakai, Yasuhiko Sato, Hiroshi Ogiwara, and Tomishige Mizoguchi

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

Abstract

On irradiation, N-(o-tolyl)phthalimides 1 possessing a variety of substituents on the benzene rings afforded indolo[2,l-a]isoindole derivatives 2 (or 3) in most cases. Phthalimides with electron-donating groups on the A ring resisted to the cyclization. The photochemical behavior of 1 qualitatively parallels that of phenyl ketones.