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Paper | Regular issue | Vol 36, No. 1, 1993, pp.123-132
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6191
Intramolecular Diels-Alder Reaction of 3-Formimidoylindoles: Synthesis of Fused Pyridoindole Compounds

Yasuo Shimoji,* Toshihiko Hashimoto, Yoji Furukawa, and Hiroaki Yanagisawa

*Sankyo Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan


Intramolecular Diels-Alder reaction of 3-formimidoylindoles having olefinic substituents at the 1-position of the indole ring gave stereoselectively fused pyridoindole compounds. Double bond migration from 2,3,3a,4,12,12a,12b,12c-octahydrobenz[de]indolo[3,2,1-ij][1,6]naphthyridin-11(1H)-ones (4) to 2,3,3a,4,5,12,12a,12b-octahydrobenz[de]indolo[3,2,1-ij][1,6]naphthyridin-11(1H)-one (5) was performed using 10% Pd-C as a catalyst.