Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

Abstract

This review examines sequential processes involving α,β-ynones and α,β-ynoates containing proximate nucleophiles as useful building blocks for the synthesis of heterocyclic derivatives through conjugate-addition-type, pericyclic and transition-metal-catalyzed transfer hydrogenation, hydroarylation, hydrovinylation, or hydroalkynylation reactions followed by heterocyclization.

1 Introduction

2 Conjugate Addition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

2.1 Conjugate Addition–Annulation Reactions of β-(2-Amino­aryl or Heteroaryl)-α,β-Ynones

2.2 Sequential Reactions of γ-Hydroxy-α,β-Acetylenic Esters with Nucleophilic Reagents

2.3 Sequential Electrophilic Addition–Annulation Processes of α,β-Ynones Containing Proximate Nucleophiles

3 Cycloaddition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

3.1 [2+2] and [4+2] Cycloaddition–Annulation Reactions

3.2 1,3-Dipolar Cycloaddition–Annulation Reactions

4 Transition-Metal-Catalyzed Addition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

4.1 Palladium-Catalyzed Transfer Hydrogenation–Heterocyclization Processes

4.2 Palladium-Catalyzed Hydroarylation–Heterocyclization Processes

4.3 Rhodium-Catalyzed Hydroarylation–Heterocyclization Processes

4.4 Copper-Catalyzed Hydroarylation–Heterocyclization Processes

4.5 Transition-Metal-Catalyzed Hydrovinylation–Heterocyclization Processes

4.6 Transition-Metal-Catalyzed Hydroalkynylation–Heterocyclization Processes

5 Conclusion

Key words

aminoalkynones - hydroxyalkynoates - sequential reactions - annulation - heterocycles

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