Synthesis of bridged benzoazabicyclic compounds using radical translocation/cyclization reactions of 1-alkynyl-2-(o-iodobenzoyl)tetrahydroisoquinolines

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(i...

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Published inHeterocycles Vol. 52; no. 2; pp. 571 - 574
Main Authors Ikeda, M, Hamada, M, El Bialy, SAA, Matsui, K, Kawakami, S, Nakano, Y, Bayomi, SMM, Sato, T
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.02.2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DERIVATIVES
CYCLIZATION
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Summary: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.
ISSN:0385-5414
DOI:10.3987/COM-99-S91