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

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Synthesis of Heterocycles via Multicomponent Reactions I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 23))

Abstract

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.

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Abbreviations

aemim:

Aminoethyl methylimidazolium

BDMS:

Bromodimethylsulfonium bromide

bmim:

Butyl methylimidazolium

CAN:

Cerium(IV) ammonium nitrate

cat:

Catalyst

DABCO:

Diazabicyclo[2.2.2]octane

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCE:

Dichloroethane

DHP:

Dihydropyridine

DHPM:

Dihydropyrimidinone

DMF:

Dimethylformamide

ee:

Enantiomeric excess

HPLC:

High performance liquid chromatography

IBX:

2-Iodoxybenzoic acid

L*:

Ligand

LUMO:

Lowest unoccupied molecular orbital

MARDi:

Michael addition-Aldolisation-Retro-Dieckmann

MCR:

Multicomponent reaction

MS:

Molecular sieves

MW:

Microwave

PFO:

Perfluorooctanoate

p-TSA:

Para-toluenesulfonic acid

RCM:

Ring closing metathesis

rt:

Room temperature

TBAF:

Tetrabutylammonium fluoride

TEBA:

Triethylbenzylammonium chloride

THF:

Tetrahydrofurane

TMAH:

Tetramethylammonium hydroxide

TMSCl:

Trimethylsilyl chloride

Yb:

Ytterbium

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Acknowledgments

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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  1. Institut des Sciences Moléculaires de Marseille, UMR CNRS 6263 iSm2, Aix-Marseille Université – Centre Saint Jérôme, Service 531, 13397, Marseille Cedex 20, France

    Maria Mar Sanchez del Duque, Christophe Allais, Nicolas Isambert, Thierry Constantieux & Jean Rodriguez

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  1. Maria Mar Sanchez del Duque
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  2. Christophe Allais
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  3. Nicolas Isambert
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  4. Thierry Constantieux
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  5. Jean Rodriguez
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Correspondence to Thierry Constantieux or Jean Rodriguez .

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  1. Fac. Sciences, Dept. Chemistry &, VU University Amsterdam, De Boelelaan 1083, Amsterdam, 1081 HV, Netherlands

    Romano V. A. Orru

  2. Faculty of Sciences, Section of Synthetic &, VU University Amsterdam, Amsterdam, 1081 HV, Netherlands

    Eelco Ruijter

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del Duque, M.M.S., Allais, C., Isambert, N., Constantieux, T., Rodriguez, J. (2010). β-Diketo Building Blocks for MCRs-Based Syntheses of Heterocycles. In: Orru, R., Ruijter, E. (eds) Synthesis of Heterocycles via Multicomponent Reactions I. Topics in Heterocyclic Chemistry, vol 23. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_26

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