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Synthesis 2016; 48(17): 2681-2704
DOI: 10.1055/s-0035-1560451
DOI: 10.1055/s-0035-1560451
review
Aza-Michael Addition of Imidazole Analogues
Further Information
Publication History
Received: 17 May 2016
Accepted after revision: 06 June 2016
Publication Date:
15 August 2016 (online)
§ 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
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