New protocol for Biginelli reaction-a practical synthesis of Monastrol

被引:75
作者
Bose, DS [1 ]
Sudharshan, M [1 ]
Chavhan, SW [1 ]
机构
[1] Indian Inst Chem Technol, Fine Chem Lab, Div Organ Chem 3, Hyderabad 500007, Andhra Pradesh, India
关键词
mitotic; monastrol; Biginelli reaction; benzyltriethylammonium chloride; multicomponent reaction; dihydropyrimidin-2(1H)-ones;
D O I
10.3998/ark.5550190.0006.325
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, efficient, and cost-effective method has been developed for the synthesis of 3,4-dihydropyrimidin- 2(1H)-ones by a one-pot three component cyclocondensation reaction of 1,3 dicarbonyl compound, aldehyde, and urea using benzyltriethylammonium chloride as the catalyst, under solvent-free conditions: the scope of this protocol is utilized for the synthesis of mitotic Kinesin EG5 inhibitor monastrol.
引用
收藏
页码:228 / 236
页数:9
相关论文
共 36 条
[1]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .2. 3-SUBSTITUTED-4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
KIMBALL, SD ;
FLOYD, DM ;
MORELAND, S ;
SWANSON, BN ;
GOUGOUTAS, JZ ;
SCHWARTZ, J ;
SMILLIE, KM ;
MALLEY, MF .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2629-2635
[2]   SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
OREILLY, BC ;
SCHWARTZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5898-5907
[3]   1,4-CYCLOADDITION OF 1,3-DIAZABUTADIENES WITH ENAMINES - AN EFFICIENT ROUTE TO THE PYRIMIDINE RING [J].
BARLUENGA, J ;
TOMAS, M ;
BALLESTEROS, A ;
LOPEZ, LA .
TETRAHEDRON LETTERS, 1989, 30 (34) :4573-4576
[4]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[5]  
2-A
[6]   A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF [J].
Bigi, F ;
Carloni, S ;
Frullanti, B ;
Maggi, R ;
Sartori, G .
TETRAHEDRON LETTERS, 1999, 40 (17) :3465-3468
[7]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[8]   A remarkable rate acceleration of the one-pot three-component cyclo-condensation reaction at room temperature: An expedient synthesis of mitotic Kinesin Eg5 inhibitor monastrol [J].
Bose, DS ;
Kumar, RK ;
Fatima, L .
SYNLETT, 2004, (02) :279-282
[9]   Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction:: Comparison of ethanol, water, and solvent-free conditions [J].
Bose, DS ;
Fatima, L ;
Mereyala, HB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :587-590
[10]  
Bose DS, 2001, J CHEM RES, P36