β-Diketo Building Blocks for MCRs-Based Syntheses of Heterocycles

  • Maria Mar Sanchez del Duque
  • Christophe Allais
  • Nicolas Isambert
  • Thierry ConstantieuxEmail author
  • Jean RodriguezEmail author
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 23)


In the context of sustainable chemistry, because of economic and ecological increasing pressure, domino multicomponent reactions (MCRs) constitute a central academic and industrial investigation domain in diversity-oriented synthesis of functionalized heterocycles. Although isocyanide-based MCRs generally predominate nowadays, the use of 1,3-dicarbonyls as substrates, proposed as early as 1882 by Hantzsch, proved to be highly efficient, but have been relatively unexplored until recently. In the last few years, such transformations received a growing attention as new useful methodologies valuable for the selective direct access to highly functionalized small organic molecules of primary synthetic and biological value. This review focuses on the more significant recent developments on the use of β-diketo building blocks for MCRs published in the last 5 years.


1,3-Dicarbonyls Biginelli reaction Hantzsch reaction Heterocyclic chemistry Knoevenagel condensation Mannich reaction Michael addition Multicomponent reactions 



Aminoethyl methylimidazolium


Bromodimethylsulfonium bromide


Butyl methylimidazolium


Cerium(IV) ammonium nitrate
















Enantiomeric excess


High performance liquid chromatography


2-Iodoxybenzoic acid




Lowest unoccupied molecular orbital


Michael addition-Aldolisation-Retro-Dieckmann


Multicomponent reaction


Molecular sieves






Para-toluenesulfonic acid


Ring closing metathesis


Room temperature


Tetrabutylammonium fluoride


Triethylbenzylammonium chloride




Tetramethylammonium hydroxide


Trimethylsilyl chloride





C.A. thanks the French Research Ministry for a fellowship award. CNRS (UMR 6263 iSm2 and RDR2 research network), National Research Agency (ANR), French Research Ministry, University Paul Cézanne and Ville de Marseille are acknowledged for financial support.


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Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  • Maria Mar Sanchez del Duque
    • 1
  • Christophe Allais
    • 1
  • Nicolas Isambert
    • 1
  • Thierry Constantieux
    • 1
    Email author
  • Jean Rodriguez
    • 1
    Email author
  1. 1.Institut des Sciences Moléculaires de Marseille, UMR CNRS 6263 iSm2Aix-Marseille Université – Centre Saint JérômeMarseille Cedex 20France

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