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Synthesis 2012(2): 159-174  
DOI: 10.1055/s-0031-1289636
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Carbo- and Heterocycles via Coupling-Isomerization Reactions

Thomas J. J. Müller*
Institut für Organische Chemie und Makromolekular Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany
Fax: +49(211)8114324; e-Mail: ThomasJJ.Mueller@uni-duesseldorf.de;
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Publikationsverlauf

Received 20 September 2011
Publikationsdatum:
05. Dezember 2011 (online)

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Abstract

The coupling-isomerization reaction is an unusual outcome of the Sonogashira coupling of propargyl alcohols, N-tosyl­amines, or ethers with preferentially electron-deficient (hetero)aryl halides. As a result, chalcones, enimines and allenyl ethers are generated in situ. The former two are readily transformed into heterocycles in consecutive cyclization and cyclocondensations in a one-pot fashion, whereas the latter are excellent entries into pericyclic domino processes for the rapid construction of complex polycyclic scaffolds.

1 Introduction

2 Michael Systems by Coupling-Isomerization Reactions (CIR)

2.1 EWG-Substituted Propenones by CIR

2.2 EWG-Substituted Propenimines by CIR

2.3 General Microwave-Assisted Coupling-Isomerization Reaction (MACIR)

3 Multicomponent Synthesis of Heterocycles by CIR-Cyclocondensation Sequences

3.1 Pyrazolines by CIR-Cyclocondensation Sequence

3.2 Pyrimidines by CIR-Cyclocondensation Sequence

3.3 Benzoheteroazepines by CIR-Cyclocondensation Sequence

3.4 Furans and Pyrroles by CIR-Stetter-Cyclocondensation Sequences

3.4.1 1,4-Diketones by CIR-Stetter Sequence

3.4.2 Furans by CIR-Stetter-Cyclocondensation Sequence

3.4.3 Pyrroles by CIR-Stetter-Cyclocondensation Sequence

3.5 Annelated and Substituted Pyridines by CIR-Cycloaddition-Cyclocondensation Sequence

3.6 Annelated and Substituted Pyridines by CIR-Cycloaddition Sequence

4 Domino Syntheses Initiated by CIR

4.1 CIR Domino Syntheses of 2-Substituted Quinolines

4.2 CIR-Diels-Alder Domino Syntheses of Polycyclic Skeletons

4.3 Mechanistic Dichotomies in CIR Domino Syntheses

5 Conclusions

Key words

alkynes - cross-coupling - domino reaction - isomerization - multicomponent reaction

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