Phenylphosphinic acid-catalyzed synthesis of 6-unsubstituted dihydropyrimidinones under solvent-free conditions

被引:3
作者
Alinezhad, Heshmatollah [1 ]
Tajbakhsh, Mahmood [1 ]
Zare, Mahboobeh [2 ]
Mousavi, Mahboobeh [1 ]
机构
[1] Univ Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar, Iran
[2] Amol Univ Special Modern Technol, Fac Sci & Herbs, Dept Basic Sci, Amol, Iran
关键词
ENAMINONES;
D O I
10.1002/hc.21327
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Phenylphosphinic acid is found to catalyze the three-component condensation of an aldehyde, enaminone, and urea or thiourea to afford the corresponding 6-unsubstituted dihydropyrimidinones in high to excellent yields. This methodology is simple and fast synthetic route for the preparation of interesting class of heterocycles.
引用
收藏
页码:290 / 294
页数:5
相关论文
共 25 条
[1]   Enaminones in Heterocyclic Synthesis: A Novel Route to Tetrahydropyrimidines, Dihydropyridines, Triacylbenzenes and Naphthofurans under Microwave Irradiation [J].
Al-Mousawi, Saleh Mohammed ;
El-Apasery, Morsy Ahmed ;
Elnagdi, Mohamed H. .
MOLECULES, 2010, 15 (01) :58-67
[2]   One-pot regioselective synthesis of 1,4,5-trisubstituted pyrazoles under solvent-free conditions without catalyst [J].
Alinezhad, Heshmatollah ;
Tajbakhsh, Mahmood ;
Zare, Mahboobeh .
MONATSHEFTE FUR CHEMIE, 2012, 143 (06) :947-950
[3]   A chemo- and regio-selective three-component dihydropyrimidinone synthesis [J].
Bailey, Chris D. ;
Houlden, Chris E. ;
Bar, Gregory L. J. ;
Lloyd-Jones, Guy C. ;
Booker-Milburn, Kevin I. .
CHEMICAL COMMUNICATIONS, 2007, (28) :2932-2934
[4]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[5]   p-Sulfonic acid calixarenes as efficient and reusable organocatalysts for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/-thiones [J].
da Silva, Daniel L. ;
Fernandes, Sergio A. ;
Sabino, Adao A. ;
de Fatima, Angelo .
TETRAHEDRON LETTERS, 2011, 52 (48) :6328-6330
[6]   A One-Pot Biginelli Synthesis of 6-Unsubstituted 5-Aroylpyrimidin-2(1H)-ones and 6-Acetyl-1,2,4-triazin-3(2H)-ones [J].
Darwish, Elham Sayed ;
Abdelhamid, Ismail Abdelshafy ;
Nasra, Miead Adel ;
Abdel-Gallil, Fathy Mohamed ;
Fleita, Daisy Hanna .
HELVETICA CHIMICA ACTA, 2010, 93 (06) :1204-1208
[7]  
Hassaneen HME, 2013, CURR ORG SYNTH, V10, P974
[8]  
Kolosov M. A., 2005, ZH ORG FARM KHIM, V3, P17
[9]   Tunable carbon-carbon and carbon-sulfur cross-coupling of boronic acids with 3,4-dihydropyrimidine-2-thiones [J].
Lengar, A ;
Kappe, CO .
ORGANIC LETTERS, 2004, 6 (05) :771-774
[10]   Nucleosides and nucleotides .152. 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil as a broad spectrum antitumor nucleoside [J].
Matsuda, A ;
Hattori, H ;
Tanaka, M ;
Sasaki, T .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (16) :1887-1892