Sulfonated Carbon Catalyzed Biginelli Reaction for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and -thiones

被引:65
作者
Moghaddas, Maryam [1 ]
Davoodnia, Abolghasem [1 ]
Heravi, Majid M. [2 ]
Tavakoli-Hoseini, Niloofar [1 ]
机构
[1] Islamic Azad Univ, Dept Chem, Mashhad Branch, Mashhad, Iran
[2] Alzahra Univ, Dept Chem, Sch Sci, Tehran, Iran
关键词
sulfonated carbon; solid acid; Biginelli reaction; heterogeneous catalysis; solvent-free condition; SOLVENT-FREE CONDITIONS; ACIDIC IONIC LIQUID; REUSABLE CATALYST; SOLID ACID; 1,2,4,5-TETRASUBSTITUTED IMIDAZOLES; 12-TUNGSTOPHOSPHORIC ACID; EFFICIENT; DIHYDROPYRIMIDINONES; DERIVATIVES; GREEN;
D O I
10.1016/S1872-2067(11)60377-X
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A sulfonated carbon material was shown to be a highly efficient, eco-friendly, and recyclable solid acid catalyst for the Biginelli reaction of beta-ketoester, aldehyde, and urea or thiourea under solvent-free conditions. It gave 3,4-dihydropyrimidin-2(1H)-ones and -thiones in good to excellent yields. This method has the advantages of a simple procedure with easy work-up, short reaction time, and high yields. The catalyst can be recycled after a simple work-up and was reused four times without substantial reduction in activity.
引用
收藏
页码:706 / 710
页数:5
相关论文
共 42 条
[21]   A catalytic method for synthesis of Biginelli-type 3,4-dihydropyrimidin-2 (1H)-one using 12-tungstophosphoric acid [J].
Heravi, MM ;
Derikvand, F ;
Bamoharram, FF .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 242 (1-2) :173-175
[22]   CuI as reusable catalyst for the Biginelli reaction [J].
Kalita, Hima Rani ;
Phukan, Prodeep .
CATALYSIS COMMUNICATIONS, 2007, 8 (02) :179-182
[23]  
KAPPE CO, 1993, TETRAHEDRON, V49, P6937
[24]   Solvent-Free Heterocyclic Synthesis [J].
Martins, Marcos A. P. ;
Frizzo, Clarissa P. ;
Moreira, Dayse N. ;
Buriol, Lilian ;
Machado, Pablo .
CHEMICAL REVIEWS, 2009, 109 (09) :4140-4182
[25]   Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen [J].
Mayer, TU ;
Kapoor, TM ;
Haggarty, SJ ;
King, RW ;
Schreiber, SL ;
Mitchison, TJ .
SCIENCE, 1999, 286 (5441) :971-974
[26]   A novel sulfonated carbon composite solid acid catalyst for biodiesel synthesis [J].
Mo, Xunhua ;
Lotero, Edgar ;
Lu, Changqing ;
Liu, Yijun ;
Goodwin, James G. .
CATALYSIS LETTERS, 2008, 123 (1-2) :1-6
[27]   Acid-catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon [J].
Okamura, Mai ;
Takagaki, Atsushi ;
Toda, Masakazu ;
Kondo, Junko N. ;
Domen, Kazunari ;
Tatsumi, Takashi ;
Hara, Michikazu ;
Hayashi, Shigenobu .
CHEMISTRY OF MATERIALS, 2006, 18 (13) :3039-3045
[28]   Water-tolerant solid acid catalysts [J].
Okuhara, T .
CHEMICAL REVIEWS, 2002, 102 (10) :3641-3665
[29]   NOVEL ALKALOIDS FROM THE SPONGE BATZELLA SP - INHIBITORS OF HIV GP120-HUMAN CD4 BINDING [J].
PATIL, AD ;
KUMAR, NV ;
KOKKE, WC ;
BEAN, MF ;
FREYER, AJ ;
DEBROSSE, C ;
MAI, S ;
TRUNEH, A ;
FAULKNER, DJ ;
CARTE, B ;
BREEN, AL ;
HERTZBERG, RP ;
JOHNSON, RK ;
WESTLEY, JW ;
POTTS, BCM .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1182-1188
[30]   Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones [J].
Reddy, CV ;
Mahesh, M ;
Raju, PVK ;
Babu, TR ;
Reddy, VVN .
TETRAHEDRON LETTERS, 2002, 43 (14) :2657-2659