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Issue 15, 1997
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Synthesis of pyrrolizin-3-ones by flash vacuum pyrolysis ofpyrrol-2-ylmethylidene Meldrum’s acid derivatives and3-(pyrrol-2-yl)propenoic esters

Abstract

Monosubstituted pyrrolizin-3-ones 1 with substituents at the 1-, 5-, 6- or 7-positions are prepared in excellent yield by flash vacuum pyrolysis (FVP) of appropriate Meldrum’s acid derivatives 2. The mechanism involves formation of the pyrrol-2-ylmethylideneketene 29, which can also be generated thermally from 3-(pyrrol-2-yl)propenoate esters (e.g. 30). This alternative route has been used to make a range of 2-substituted pyrrolizin-3-ones, again in excellent yield. The 3-oxo-3H-pyrrolizine-2-carboxylic acid 42 could not be made in this way owing to facile decarboxylation to pyrrolizinone 1, and extension to the formation of the azaazulenone 48 was again unsuccessful.

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Article type: Paper
DOI: 10.1039/A701749I
Citation: J. Chem. Soc., Perkin Trans. 1, 1997, 2195-2202
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    Synthesis of pyrrolizin-3-ones by flash vacuum pyrolysis of pyrrol-2-ylmethylidene Meldrum’s acid derivatives and 3-(pyrrol-2-yl)propenoic esters

    S. E. Campbell, M. C. Comer, P. A. Derbyshire, X. L. M. Despinoy, H. McNab, R. Morrison, C. C. Sommerville and C. Thornley, J. Chem. Soc., Perkin Trans. 1, 1997, 2195
    DOI: 10.1039/A701749I

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