An Efficient One-pot Two-component Protocol for Regio- and Chemoselective Synthesis of 5-Aryloyl-1,3,7,9-tetraalkyl-2,8-dithioxo-2,3,8,9-tetrahydro-1H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(5H,7H)-diones

被引:16
作者
Rimaz, Mehdi [1 ]
Rabiei, Hossein [1 ]
Khalili, Behzad [2 ]
Prager, Rolf H. [3 ]
机构
[1] Payame Noor Univ, Dept Chem, Tehran, Iran
[2] Univ Guilan, Dept Chem, Fac Sci, Rasht, Iran
[3] Flinders Univ S Australia, Sch Chem Phys & Earth Sci, Adelaide, SA 5001, Australia
关键词
3 COMPONENT SYNTHESIS; MULTICOMPONENT REACTIONS; REGIOSELECTIVE SYNTHESIS; SULFUR ANALOGS; CHEMISTRY; 4-HYDROXYCOUMARIN; DERIVATIVES; LIBRARIES;
D O I
10.1071/CH13438
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel symmetric fused pyrano[2,3-d]pyrimidine derivatives were synthesized in 75-92 % yield by a one-pot two-component reaction of arylglyoxals and 1,3-dialkyl-2-thiobarbituric acids in ethanol at room temperature. This is the first protocol to be reported for the synthesis of 5-aryloyl-1,3,7,9-tetraalkyl-2,8-dithioxo-2,3,8,9-tetrahydro-1H-pyrano[2,3-d:6,5-d ']dipyrimidine-4,6(5H,7H)-diones and the significant features of the present protocol are simplicity, high yields, a simple isolation procedure, and high chemoselectivity.
引用
收藏
页码:283 / 288
页数:6
相关论文
共 49 条
[1]   Pd-assisted multicomponent synthesis of heterocycles [J].
Balme, G ;
Bossharth, E ;
Monteiro, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111
[2]  
Bannwarth W., 2000, COMBINATORIAL CHEM
[3]   4-hydroxycoumarin in heterocyclic synthesis -: Part III.: Synthesis of some new pyrano[2,3-d]pyrimidine, 2-substituted[1,2,4]triazolo[1,5-c]pyrimidine and pyrimido[1,6-b][1,2,4]triazine derivatives [J].
Bedair, AH ;
El-Hady, NA ;
Abd El-Latif, MS ;
Fakery, AH ;
El-Agrody, AM .
FARMACO, 2000, 55 (11-12) :708-714
[4]   ASYMMETRIC-SYNTHESIS .3. SYNTHESIS OF (2R)-(+)-2,3-DIHYDRO-2,6-DIMETHYL-4H-PYRAN-4-ONE, A HOMOLOG OF PHEROMONES OF A SPECIES IN THE HEPIALIDAE FAMILY [J].
BIANCHI, G ;
TAVA, A .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1987, 51 (07) :2001-2002
[5]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[6]  
2-A
[7]   Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents [J].
Bollini, Mariela ;
Domaoal, Robert A. ;
Thakur, Vinay V. ;
Gallardo-Macias, Ricardo ;
Spasov, Krasimir A. ;
Anderson, Karen S. ;
Jorgensen, William L. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (24) :8582-8591
[8]  
Brown D. J., 1984, COMPREHENSIVE HETERO, V3, P443
[9]   Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from Methyleneaziridines Using a Four-Component Reaction [J].
Cariou, Claire C. A. ;
Clarkson, Guy J. ;
Shipman, Michael .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (24) :9762-9764
[10]   Multi-component syntheses of heterocycles by transition-metal catalysis [J].
D'Souza, Daniel M. ;
Mueller, Thomas J. J. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108