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Synthesis 2006(17): 2799-2814
DOI: 10.1055/s-2006-942549
DOI: 10.1055/s-2006-942549
REVIEW
© Georg Thieme Verlag Stuttgart · New York3,5-Dihalo-2(1H)-pyrazinones: Versatile Scaffolds in Organic Synthesis
Weitere Informationen
Received
7 February 2006
Publikationsdatum:
15. August 2006 (online)
Publikationsverlauf
Publikationsdatum:
15. August 2006 (online)
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.
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1 Introduction
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2 Synthesis of 3,5-Dihalo-2(1H)-pyrazinones
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3 Functionalisation of the Scaffold
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3.1 Functionalisation at C3
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3.2 Functionalisation at C5
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3.3 Deblocking of N1
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3.4 Alkylation of N1
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4 Diels-Alder Reactions
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4.1 Cycloaddition Reactions with Alkynes
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4.2 Cycloaddition Reactions with Alkenes
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5 Application of 2(1H)-Pyrazinones in Drug and Peptidomimetic Design
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6 Solid-Phase Chemistry
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7 Conclusion
Key words
pyrazinone - Diels-Alder reaction - nucleophilic aromatic substitution - cross-coupling reactions - peptidomimetic chemistry
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