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

Author:

Comesse SébastienORCID,Alahyen Ismail,Benhamou Laure,Dalla Vincent,Taillier Catherine

Abstract

AbstractAcrylamides 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 Introduction2 Metal-Free Annulations2.1 Domino Reactions Triggered by a Michael Addition2.2 Domino Reactions Triggered by an Aza-Michael Addition2.3 Domino Processes Triggered by an Acylation Reaction2.4 Domino Reactions Triggered by a Baylis–Hillman Reaction2.5 Cycloadditions and Domino Reactions2.6 Miscellaneous Domino Reactions3 Metal-Triggered/Mediated Annulations3.1 Zinc-Promoted Transformations3.2 Rhodium-Catalyzed Functionalization/Annulation Cascades3.3 Cobalt-Catalyzed Functionalization/Annulation Cascades3.4 Ruthenium-Catalyzed Functionalization/Annulation Cascades3.5 Iron-Catalyzed Functionalization/Annulation Cascades3.6 Palladium-Catalyzed Functionalization/Annulation Cascades3.7 Copper-Catalyzed Transformations3.8 Transition Metals Acting in Tandem in Domino Processes4 Radical Cascade Reactions5 Conclusion

Funder

Centre National de la Recherche Scientifique

Région Normandie

URCOM

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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