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Palladium-Copper Catalyzed Alkyne Activation as an Entry to Multicomponent Syntheses of Heterocycles

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Synthesis of Heterocycles via Multicomponent Reactions II

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 25))

Abstract

Alkynones and chalcones are of paramount importance in heterocyclic chemistry as three-carbon building blocks. In a very efficient manner, they can be easily generated by palladium-copper catalyzed reactions: ynones are formed from acid chlorides and terminal alkynes, and chalcones are synthesized in the sense of a coupling-isomerization (CI) sequence from (hetero)aryl halides and propargyl alcohols. Mild reaction conditions now open entries to sequential and consecutive transformations to heterocycles, such as furans, 3-halo furans, pyrroles, pyrazoles, substituted and annelated pyridines, annelated thiopyranones, pyridimines, meridianins, benzoheteroazepines and tetrahydro-β-carbolines, by consecutive coupling-cyclocondensation or CI-cyclocondensation sequences, as new diversity oriented routes to heterocycles. Domino reactions based upon the coupling-isomerization reaction (CIR) have been probed in the synthesis of antiparasital 2-substituted quinoline derivatives and highly luminescent spiro-benzofuranones and spiro-indolones.

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Abbreviations

Ac:

Acetyl

AcO:

Acetyloxy

atm:

Atmosphere [bar]

Boc:

Tert-butyloxycarbonyl

Bu:

Butyl

CNS:

Central nervous system

COX-2:

Cyclooxygenase-2

Δ:

Heating

DBU:

Diazabicyclo[5.4.0]undecene

DFT:

Density functional theory

DMF:

N,N-dimethylformamide

DME:

1,2-Dimethoxyethane

equiv:

Equivalent(s)

EWG:

Electron-withdrawing group

Et:

Ethyl

GC-MS:

Gas chromatography-mass spectrometry

Hal:

Halogen

HIV:

Human immunodeficiency virus

HMG-CoA:

3-Hydroxy-3-methyl-glutaryl-CoA

kobs :

Observed rate constant

L:

Ligand

LUMO:

Lowest unoccupied molecular orbital

MCR:

Multicomponent reaction

Me:

Methyl

MW:

(Heated in a) microwave (oven)

nCR:

n-Component reaction

NMP:

N-Methylpyrrolidone

Nu:

Nucleophile

OLED:

Organic light emitting diode

π:

Conjugated π-electron system

Ph:

Phenyl

Pr:

Propyl

PTSA:

p-Toluenesulfonic acid

R:

Organic substituent

r.t.:

Room temperature (20°C)

THF:

Tetrahydrofuran

THP:

Tetrahydropyranyl

TLC:

Thin layer chromatography

TBDMS:

Tert-butyldimethylsilyl

Tos:

p-Tolylsulfonyl

TMS:

Trimethylsilyl

UV:

Ultraviolet

vis:

Visible

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Acknowledgments

The work summarized in this account was continuously supported by the Deutsche Forschungsgemeinschaft, the MORPHOCHEM AG, Merck Serono GmbH, the Fonds der Chemischen Industrie, and the Dr.-Otto-Röhm Gedächtnisstiftung. The dedication, the intellectual input and the skill of the group members and students who actually carried out the research in the laboratories is gratefully acknowledged.

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  1. Institut für Organische Chemie und Makromolekulare Chemie der Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225, Düsseldorf, Germany

    Thomas J. J. Müller

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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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Müller, T.J.J. (2010). Palladium-Copper Catalyzed Alkyne Activation as an Entry to Multicomponent Syntheses of Heterocycles. In: Orru, R., Ruijter, E. (eds) Synthesis of Heterocycles via Multicomponent Reactions II. Topics in Heterocyclic Chemistry, vol 25. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_43

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