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Paper | Special issue | Vol 95, No. 2, 2017, pp.844-861
Published online, 8th December, 2016
DOI: 10.3987/COM-16-S(S)53
Nucleophilic Substitution Reactions on Indole Nucleus: Formation of (3a,8a-cis)-1,2,3,3a,8,8a-Hexahydropyrrolo[2,3-b]indoles Having a Substituent at the 3a-Position

Fumio Yamada, Aya Goto, Masakazu Hasegawa, Kensuke Kobayashi, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan

Abstract

Various nucleophiles, such as indole, 1,2,3-trimethoxybenzene, anisole, phenol, and pyrrole, reacted with 1-hydroxy-Nb-trifluoroacetyltryptamine under the presence of mesyl chloride to give novel series of (3a,8a-cis)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles having a substituent at the 3a-position. Their structures and by-products were strictly determined.