TY - JOUR
T1 - A new and practical method for the synthesis of 6-aryl-5,6-dihydropyrido[2, 3-d]pyrimidine-4,7(3H,8H)-diones
AU - Camarasa, Marta
AU - Barnils, Christian
AU - Puig De La Bellacasa, Raimon
AU - Teixidó, Jordi
AU - Borrell, José I.
N1 - Funding Information:
Acknowledgments Financial support by the Spanish Ministerio de Economia y Competividad Project SAF2010-C21617-C02 is greatly acknowledged. M. Camarasa wants to thank IQS for a scholarship.
PY - 2013/8
Y1 - 2013/8
N2 - A one step general synthetic methodology for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-diones (17{x} (G = NH 2) and 20{x } (G = SMe) is described. This methodology is based on reacting a 2-aryl-substituted acrylate (16{x}) with the corresponding 6-aminopyrimidin-4(3H) -one (13 (G=NH2)); 19 (G =SMe)) in presence of a base under microwave irradiation. The resulting pyrido[2,3-d ]pyrimidines present an aryl substituent at position C6, precisely the one directly related to the biological activity of such heterocycles. These protocols have been extended to other 2-alkyl-substituted and 3-alkyl (or aryl)-substituted acrylates but with lower yields.
AB - A one step general synthetic methodology for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-diones (17{x} (G = NH 2) and 20{x } (G = SMe) is described. This methodology is based on reacting a 2-aryl-substituted acrylate (16{x}) with the corresponding 6-aminopyrimidin-4(3H) -one (13 (G=NH2)); 19 (G =SMe)) in presence of a base under microwave irradiation. The resulting pyrido[2,3-d ]pyrimidines present an aryl substituent at position C6, precisely the one directly related to the biological activity of such heterocycles. These protocols have been extended to other 2-alkyl-substituted and 3-alkyl (or aryl)-substituted acrylates but with lower yields.
KW - 2-Aryl acrylates
KW - 4-Oxopyrido[2,3-d ]pyrimidines
KW - 6-Aminopyrimidine-4 (3H) -ones
KW - Michael addition
KW - Pyrido[2,3-d ]pyrimidines
UR - https://www.scopus.com/pages/publications/84880814089
UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000321912600011&DestLinkType=FullRecord&DestApp=WOS
U2 - 10.1007/s11030-013-9450-1
DO - 10.1007/s11030-013-9450-1
M3 - Article
C2 - 23709350
AN - SCOPUS:84880814089
SN - 1381-1991
VL - 17
SP - 525
EP - 536
JO - Molecular Diversity
JF - Molecular Diversity
IS - 3
ER -