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Synthesis 2006(17): 2799-2814  
DOI: 10.1055/s-2006-942549
REVIEW
© Georg Thieme Verlag Stuttgart · New York

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;
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Publikationsverlauf

Received 7 February 2006
Publikationsdatum:
15. August 2006 (online)

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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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