3,5-Dihalo-2(1H)-pyrazinones: Versatile Scaffolds in Organic Synthesis

Vijaykumar G. Pawar; Wim M. De Borggraeve

doi:10.1055/s-2006-942549

REVIEW

3,5-Dihalo-2(1H)-pyrazinones: Versatile Scaffolds in Organic Synthesis

Vijaykumar G. Pawar, Wim M. De Borggraeve*
Chemistry Department, Molecular Design and Synthesis, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Fax: +32(16)327990; e-Mail: Wim.DeBorggraeve@chem.kuleuven.be;

Abstract

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Abstract

3,5-Dihalo-2(1H)-pyrazinones have proven to be versatile scaffolds in organic synthesis. This review describes the methods to synthesise and functionalise these compounds. Applications of the 2(1H)-pyrazinone scaffold in peptide mimicry and drug design are discussed.

1 Introduction
2 Synthesis of 3,5-Dihalo-2(1H)-pyrazinones
3 Functionalisation of the Scaffold
3.1 Functionalisation at C³
3.2 Functionalisation at C⁵
3.3 Deblocking of N¹
3.4 Alkylation of N¹
4 Diels-Alder Reactions
4.1 Cycloaddition Reactions with Alkynes
4.2 Cycloaddition Reactions with Alkenes
5 Application of 2(1H)-Pyrazinones in Drug and Peptidomimetic Design
6 Solid-Phase Chemistry
7 Conclusion

Key words

pyrazinone - Diels-Alder reaction - nucleophilic aromatic substitution - cross-coupling reactions - peptidomimetic chemistry

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