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Paper | Regular issue | Vol 94, No. 12, 2017, pp.2229-2246
Published online, 10th October, 2017
DOI: 10.3987/COM-17-13793
Cationic Au(I)-Catalyzed Cycloisomerization of N-(2-Alkynylphenyl)indolines for the Construction of Indolobenzazepine Skeleton

Mamoru Ito, Daisuke Inoue, Ryosuke Kawasaki, Kyalo Stephen Kanyiva, and Takanori Shibata*

*Chemistry and Biochemistry, Advanced Research Center of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

An intramolecular reaction of N-(2-alkynylphenyl)indolines proceeded efficiently to give indolo[1,7-ab][1]benzazepine derivatives in high to excellent yields by cationic Au(I)-catalyzed 7-endo-dig selective cycloisomerization along with DDQ oxidation. The present transformation could be used for the intramolecular reaction of N-(2-alkynylphenyl)-1,2,3,4-tetrahydroquinoline and N-(2-alkynylphenyl)-N-methylaniline, and construction of a dibenzazepine skeleton was achieved.