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Communication | Regular issue | Vol 14, No. 6, 1980, pp.779-782
Published online, 1st January, 1970
DOI: 10.3987/R-1980-06-0779
Photocyclization of N-3-Alkenylphthalimides. Effect of Alkyl Substitution on the Formation of Pyrroloisoindoles and Pyridoisoindoles

Minoru Machida, Kazuaki Oda, Kazuhiro Maruyama, Yasuo Kubo, and Yuichi Kanaoka*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

Photolysis of N-3-alkenylphthalimides 1 in methanol gave tetrahydro-5H-pyrrolo[2,1-a]isoindol-5-ones 2 and/or tetrahydropyrido[2,1-a]isoindol-6(2H)-ones 3 depending on the degree of substitution at the olefin carbons of 1. Electron transfer followed by the anti-Markownikoff addition of methanol is proposed as a possible mechanistic pathway.