Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries

2-Pyridone and 2-quinolone analogues are well-known biologically active heterocyclic scaffolds. Libraries of 3,5,6-substituted 2-pyridone derivatives are generated by rapid microwave assisted solution phase methods using a one-pot, two-step protocol. The three-component condensation of CH–acidic car...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 39; pp. 8633 - 8644
Main Authors Gorobets, Nikolay Yu, Yousefi, Behrooz H., Belaj, Ferdinand, Kappe, C.Oliver
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.09.2004
Elsevier
Subjects
2-Pyridones
2-Quinolones
Chemistry
Chemistry, Organic
Microwave synthesis
Multi-component reactions
Physical Sciences
Science & Technology
Multi-component reactions
Microwave synthesis
2-Pyridones
2-Quinolones
MILRINONE
ENAMINOKETONES
ONE-POT SYNTHESIS
multi-component reactions
2-pyridones
REVERSE-TRANSCRIPTASE INHIBITORS
INOTROPIC AGENTS
2-PYRIDONE-CONTAINING PEPTIDOMIMETICS
BIOLOGICAL EVALUATION
microwave synthesis
CARDIOTONIC AGENTS
DERIVATIVES
2-quinolones
STRUCTURE-BASED DESIGN
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Summary:2-Pyridone and 2-quinolone analogues are well-known biologically active heterocyclic scaffolds. Libraries of 3,5,6-substituted 2-pyridone derivatives are generated by rapid microwave assisted solution phase methods using a one-pot, two-step protocol. The three-component condensation of CH–acidic carbonyl compounds, N, N-dimethylformamide dimethylacetal and methylene active nitriles, leads to 2-pyridones and fused analogues in moderate to good overall yields and high purities. The proposed mechanism of this novel multi-component reaction, structure elucidation of products and intermediates are discussed. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.05.100