Sugars in Multicomponent Reactions: A Toolbox for Diversity-Oriented Synthesis

Abstract

Multicomponent reactions (MCRs) cover strategically employed chemical transformations that incorporate three or more reactants in one pot leading to a functionalized final product. Thus, it is an ideal tool to achieve high levels of complexity, diversity, yields of desired products, atom economy, and reduced reaction times. Sugars belong to the class of naturally occurring compounds with fascinating applications in the field of drug discovery due to the presence of various hydroxy groups and well-defined stereochemistry. However, their potential in MCRs has been realized only recently. This account describes recent advances in the synthesis of sugar-derived heterocycles synthesized by MCRs. We hope to encourage the synthetic and medicinal chemistry community to apply this powerful MCR chemistry to generate novel glycoconjugate challenges.

1 Introduction

2 Synthesis of Various Functionalized Sugar Compounds

2.1 Passerini and Ugi Multicomponent Reactions

2.2 Petasis Reaction

2.3 Hantzsch Reaction

2.4 Domino Ferrier–Povarov Reaction

2.5 Marckwald Reaction

2.6 Groebke–Blackburn–Bienaymé (GBB) Reaction

2.7 Prins–Ritter Reaction

2.8 Debus–Radziszewski Imidazole Synthesis Reaction

2.9 Mannich Reaction

2.10 A³-Coupling Reaction

2.11 [3+2]-Cycloaddition Reactions

2.12 Miscellaneous Reactions

3 Conclusion

Key words

sugars - multicomponent reactions - isocyanides - aldehydes - domino reactions

Publikationsverlauf

Eingereicht: 22. November 2022

Angenommen nach Revision: 17. Januar 2023

Artikel online veröffentlicht:
02. März 2023

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