Synthesis of bridged azabicyclic compounds using radical translocation reactions of 1-(o-halogenobenzoyl)-2-(prop-2-enyl)- and -(prop-2-ynyl)-piperidines

被引：27

作者：

Ikeda, M

Kugo, Y

Sato, T

机构：

[1] Kyoto Pharmaceutical University, Misasagi, Yamashina

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 15期

关键词：

D O I：

10.1039/p19960001819

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)piperidine-2-carboxylate upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave regioselectively the 8-aza-bicyclo[3.2.1] octane 14a (a 5-exo cyclisation product) in quantitative yield as a diastereomeric mixture (66:34), 1-(o-Bromobenzoyl)-2-(prop-2-enyl)piperidine 13 also gave the 8-azabicyclo[3,2,1]octane 16 (75% as a diastereomeric mixture), along with the pyrido [2,1-a]isoindolone 17 (10%) and the simple reduction product 18 (5%), 1-(o-Iodobenzoyl)-2-[3-(trimethylsilyl)prop-2-ynyl]piperidine 23 afforded, in addition to the pyrido[2,1-a]isoindolone 25 (18%), the 8-azabicyclo-[3.2.1]octane 24 (75%) which was converted into the 6-oxo derivative 27. For comparison, the behaviour of the azetidine congener 31 was also examined.

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页码：1819 / 1824

页数：6

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