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Communication | Special issue | Vol 52, No. 2, 2000, pp.571-574
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S91
Synthesis of Bridged Benzoazabicyclic Compounds Using Radical Translocation/Cyclization Reactions of 1-Alkynyl-2-(o-iodobenzoyl)tetrahydroisoquinolines

Masazumi Ikeda,* Masahiro Hamada, Serry A. A. El Bialy, Katsuaki Matsui, Shimpei Kawakami, Yuka Nakano, Said M. M. Bayomi, and Tatsunori Sato

*Kyoto Pharmaceutical University, Misasagi-Shichonocho, Yamashina, Kyorto 607-8414, Japan

Abstract

Bu3SnH-mediated radical translocation/cyclization reactions of 1-alkynyl-2-(o-iodobenzoyl)tetrahydroisoquinolines were examined. The 1-[3-(trimethylsilyl)prop-2-ynyl]- (10a) and 1-[4-(trimethylsilyl)but-3-ynyl]-1,2,3,4-tetrahydroisoquinoline derivatives (10b), with Bu3SnH in the presence of azobis(isobutyronitrile) in boiling toluene, gave regioselectively the 6,7,8,9-tetrahydro-5H-benzocyclohepten-5,8-imine (12a) and 5,6,7,8,9,10-hexahydrobenzocycloocten-5,9-imine (12b), respectively.