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
Format:	Artikel
Sprache:	eng
Schlagworte:	Aza-Diels–Alder reaction Chemistry Condensing Coupling (molecular) Diffraction Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Knoevenagel condensation l-Proline Molecular structure One-pot three-component reaction Organic chemistry Preparations and properties Pyrido[2,3- d]pyrimidine Single crystals Synthesis (chemistry) Tetrahedrons X-rays
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container_end_page	5941
container_issue	33
container_start_page	5935
container_title	Tetrahedron
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creator	Samai, Subhasis Chandra Nandi, Ganesh Chowdhury, Sushobhan Singh, Maya Shankar
description	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]
doi_str_mv	10.1016/j.tet.2011.06.051
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subjects	Aza-Diels–Alder reaction Chemistry Condensing Coupling (molecular) Diffraction Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Knoevenagel condensation l-Proline Molecular structure One-pot three-component reaction Organic chemistry Preparations and properties Pyrido[2,3- d]pyrimidine Single crystals Synthesis (chemistry) Tetrahedrons X-rays
title	l-Proline catalyzed synthesis of densely functionalized pyrido[2,3- d]pyrimidines via three-component one-pot domino Knoevenagel aza-Diels–Alder reaction
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