l-Proline catalyzed synthesis of densely functionalized pyrido[2,3- d]pyrimidines via three-component one-pot domino Knoevenagel aza-Diels–Alder reaction

Highly functionalized hitherto unreported pyrido[2,3- d]pyrimidines have been concisely synthesized in good yields via l-proline catalyzed one-pot three-component domino coupling of 6-amino-1,3-dimethyluracil, aldehydes, and dialkyl acetylenedicarboxylates under mild conditions for the first time. T...

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Veröffentlicht in:Tetrahedron 2011-08, Vol.67 (33), p.5935-5941
Hauptverfasser: Samai, Subhasis, Chandra Nandi, Ganesh, Chowdhury, Sushobhan, Singh, Maya Shankar
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Sprache:eng
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Zusammenfassung:Highly functionalized hitherto unreported pyrido[2,3- d]pyrimidines have been concisely synthesized in good yields via l-proline catalyzed one-pot three-component domino coupling of 6-amino-1,3-dimethyluracil, aldehydes, and dialkyl acetylenedicarboxylates under mild conditions for the first time. The MCR process involves Knoevenagel condensation followed by [4+2] cycloaddition reaction. No co-catalyst or activator is required for this MCR. The molecular structures of two representative pyrido[2,3- d]pyrimidines 4a and 4h were confirmed by single crystal X-ray diffraction. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.06.051