Aza-Michael Addition of Imidazole Analogues

^§ These authors contributed equally.

Abstract

This review summarizes methods of N-functionalization of imidazole and its derivatives through simple aza-Michael addition. Apart from advances in the development of efficient additives applied for this transformation, examples of this reaction’s applicability in the synthesis of biologically relevant molecules are presented.

1 Introduction

2 Method Development for Aza-Michael Addition of Imidazole Analogues­

2.1 Reactions Promoted by Catalysts

2.2 Aza-Michael Addition on Solid Support

2.3 Reactions Promoted by Base

2.4 Reactions Catalyzed by Enzymes

2.5 Reaction Promoted by Ionic Liquids

2.6 Microwave-, Pressure-, and Ultrasound-Assisted Aza-Michael Addition­

2.7 Asymmetric Aza-Michael Addition

3. Applications of Aza-Michael Addition

3.1 Addition to Doubly Activated Michael Acceptors; Side Reactions

3.2 Synthesis of Amino Acids Using Aza-Michael Addition

3.3 Domino Transformations Including Aza-Michael Addition

3.4 Application of Aza-Michael Addition in the Synthesis of Biologically­ Relevant Compounds

4 Conclusions

Key words

aza-Michael addition - imidazole - benzimidazole - purines - nitrogen nucleophiles

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