A Domino Microwave-Assisted Protocol for the Synthesis of 2,6-Disubstituted Pyrimidinones

被引：7
作者：
Radi, Marco [1 ]
Casaluce, Gianni [1 ]
Botta, Maurizio [1 ,2 ]
机构：
[1] Univ Siena, Dipartimento Farm Chim Tecnol, I-53100 Siena, Italy
[2] Temple Univ, Sbarro Inst Canc Res & Mol Med, Philadelphia, PA 19122 USA
来源：
SYNLETT | 2011年 / 14期
关键词：
microwave; pyrimidinones; acetylenecarboxylates; S-DABO; N-DABO; REVERSE-TRANSCRIPTASE; GENERATION; INHIBITORS; REAGENTS; POTENT;
D O I：
10.1055/s-0030-1261174
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical microwave-assisted protocol for the synthesis of 2,6-disubstituted pyrimidinones has been developed. This approach is based on a domino Michael addition-cyclocondensation reaction between substituted thioureas/guanidines and acetylenecarboxylates. The application of such protocol for the synthesis of not easily accessible N-DABO derivatives as potential antiviral agents is also reported.
引用
收藏
页码：1997 / 2000
页数：4
相关论文
共 26 条
[1]   Highly active antiretroviral therapy: Current state of the art, new agents and their pharmacological interactions useful for improving therapeutic outcome [J].
Barbaro, G ;
Scozzafava, A ;
Mastrolorenzo, A ;
Supuran, CT .
CURRENT PHARMACEUTICAL DESIGN, 2005, 11 (14) :1805-1843
[2]  
BARTOCCINI G, 2010, THESIS U SIENA ITALY
[3]  
Boone LR, 2006, CURR OPIN INVESTIG D, V7, P128
[4]   6-ALKYL-2-METHOXY-4(3H)-PYRIMIDINONES AND 5,6-DIALKYL-2-METHOXY-4(3H)-PYRIMIDINONES IN THE TRANSFORMATIONS OF PYRIMIDINES - CONVERSION INTO 2-SUBSTITUTED "AMINO-CHLORO-PYRIMIDINE-DERIVATIVES AND 4-CHLORO-PYRIMIDINE-DERIVATIVES [J].
BOTTA, M ;
DEANGELIS, F ;
FINIZIA, G ;
GAMBACORTA, A ;
NICOLETTI, R .
SYNTHETIC COMMUNICATIONS, 1985, 15 (01) :27-34
[5]   SYNTHESIS, ANTIMICROBIAL AND ANTIVIRAL ACTIVITIES OF ISOTRIMETHOPRIM AND SOME RELATED DERIVATIVES [J].
BOTTA, M ;
ARTICO, M ;
MASSA, S ;
GAMBACORTA, A ;
MARONGIU, ME ;
PANI, A ;
LACOLLA, P .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1992, 27 (03) :251-257
[6]  
BOTTA M, 2007, Patent No. 2007043094
[7]   Slow-, tight-binding HIV-1 reverse transcriptase non-nucleoside inhibitors highly active against drug-resistant mutants [J].
Cancio, Reynel ;
Mai, Antonello ;
Rotili, Dante ;
Artico, Marino ;
Sbardella, Gianluca ;
Clotet-Codina, Imma ;
Este, Jose A. ;
Crespan, Emmanuele ;
Zanoli, Samantha ;
Hubscher, Ulrich ;
Spadari, Silvio ;
Maga, Giovanni .
CHEMMEDCHEM, 2007, 2 (04) :445-448
[8]   Synthesis of enantiomerically pure α-[4-(1-substituted)-1,2,3-triazol-4-yl]-benzylacetamides via microwave-assisted click chemistry:: towards new potential antimicrobial agents [J].
Castagnolo, Daniele ;
Dessi, Filippo ;
Radi, Marco ;
Botta, Maurizio .
TETRAHEDRON-ASYMMETRY, 2007, 18 (11) :1345-1350
[9]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[10]  
GUPTA KA, 1981, SYNTHESIS-STUTTGART, P905
123