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

DOI: 10.1039/p19960001819

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1819 - 1824 (1996)

Update date:2022-07-30

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Authors:

Ikeda, Masazumi

Kugo, Yasuhiro

Sato, Tatsunori

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Article abstract of DOI:10.1039/p19960001819

Methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)piperidine-2-carboxylate 8a, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave regioselectively the 8-azabicyclo[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.

Full text of DOI:10.1039/p19960001819

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