20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

Abstract

Acrylamides are versatile building blocks that are easily obtained from readily available starting materials. During the last 20 years, these valuable substrates bearing a nucleophilic nitrogen atom and an electrophilic double bond have proven to be efficient domino partners, leading to a wide variety of complex aza-heterocycles of synthetic relevance. In this non-exhaustive review, metal-free and metal-triggered reactions followed by an annulation will be presented; these two approaches allow good modulation of the reactivity of the polyvalent acrylamides.

1 Introduction

2 Metal-Free Annulations

2.1 Domino Reactions Triggered by a Michael Addition

2.2 Domino Reactions Triggered by an Aza-Michael Addition

2.3 Domino Processes Triggered by an Acylation Reaction

2.4 Domino Reactions Triggered by a Baylis–Hillman Reaction

2.5 Cycloadditions and Domino Reactions

2.6 Miscellaneous Domino Reactions

3 Metal-Triggered/Mediated Annulations

3.1 Zinc-Promoted Transformations

3.2 Rhodium-Catalyzed Functionalization/Annulation Cascades

3.3 Cobalt-Catalyzed Functionalization/Annulation Cascades

3.4 Ruthenium-Catalyzed Functionalization/Annulation Cascades

3.5 Iron-Catalyzed Functionalization/Annulation Cascades

3.6 Palladium-Catalyzed Functionalization/Annulation Cascades

3.7 Copper-Catalyzed Transformations

3.8 Transition Metals Acting in Tandem in Domino Processes

4 Radical Cascade Reactions

5 Conclusion

Key words

acrylamides - domino reactions - cascade reactions - N-heterocycles - metal catalysis

Publication History

Received: 04 December 2020

Accepted after revision: 10 May 2021

Accepted Manuscript online:
10 May 2021

Article published online:
29 June 2021

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