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Synthesis 2001(14): 2059-2074
DOI: 10.1055/s-2001-18057
DOI: 10.1055/s-2001-18057
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Synthetic Applications of the Pyrolysis of Meldrum’s Acid Derivatives
Further Information
Received
11 July 2001
Publication Date:
09 August 2004 (online)
Publication History
Publication Date:
09 August 2004 (online)
Abstract
The pyrolysis of Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione) 1 derivatives in solution and in the gas-phase takes place by loss of acetone and carbon dioxide to provide ketene intermediates. In particular, methylene Meldrum’s acid derivatives 7 often provide methyleneketenes 8, which act as substrates for internal hydrogen transfer leading to cyclisation reactions. The availability of versatile synthetic routes to 7 (in particular R = heteroatom) has led to the efficient preparation of a diverse range of cyclic compounds such as quinolinones, 3-hydroxythiophenes, naphthols, azepin-3(2H)-ones or pyrrolizin-3-ones initiated respectively by 1,3- 1,4- 1,5- 1,6- or 1,7-prototropic shifts. These reactions are discussed in the context of a rigorous understanding of the chemistry of the ketene intermediates involved. Most of the work was published in the period 1980-2000 but important references to earlier literature are also included.
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1 Introduction
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2 Meldrum’s Acid Derivatives
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2.1 Cyclisations and Other Processes Preceded by a 1,3-Prototropic Shift
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2.2 Cyclisations Preceded by a 1,4-Prototropic shift
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2.3 Cyclisations Preceded by a 1,5-Prototropic Shift
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2.4 Cyclisations Preceded by a 1,6-Prototropic Shift and Related Reactions
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2.5 Cyclisations Preceded by a 1,7- Prototropic Shift
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2.6 Cyclisations Involving Remote Prototropic Shifts
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2.7 Eliminations and other Non-Cyclisation Processes
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3 Coda
Key words
heterocycles - hydrogen transfer - pericyclic reactions - Meldrum’s acid - pyrolysis
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