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DOI: 10.1055/s-0031-1289636
Synthesis of Carbo- and Heterocycles via Coupling-Isomerization Reactions
Publication History
Publication Date:
05 December 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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