Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates.: One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones

被引:281
作者
Lu, J [1 ]
Bai, YJ [1 ]
机构
[1] NW Univ Xian, Dept Chem, Shaanxi Prov Key Lab Physicoinorgan Chem, Xian 710069, Shaanxi, Peoples R China
来源
SYNTHESIS-STUTTGART | 2002年 / 04期
关键词
Biginelli reaction; dihydropyrimidine-2(1H)-ones; nickel chloride hexahydrate; ferric chloride hexahydrate;
D O I
10.1055/s-2002-20956
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of 3.4-dihydropyrimidinones from the aldehyde. beta-keto ester and urea in ethanol. using ferric chloride hexahydrate or nickel chloride hexahydrate as the catalyst, is described. Compared with the classical Biginelli reaction conditions, this new method has the advantage of excellent yields (53-97%) and short reaction time (4-5 hours).
引用
收藏
页码:466 / 470
页数:5
相关论文
共 33 条
[1]   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
[2]  
Christoffers J, 2001, SYNLETT, P723
[3]   Iron(III) catalysis of the Michael reaction of 1,3-dicarbonyl compounds and enones [J].
Christoffers, J .
CHEMICAL COMMUNICATIONS, 1997, (10) :943-944
[4]  
CHRISTOFFERS J, 2000, CHEM COMMUN, P701
[5]   Parallel synthesis of dihydropyrimidinones using Yb(III)-resin and polymer-supported scavengers under solvent-free conditions. A green chemistry approach to the Biginelli reaction [J].
Dondoni, A ;
Massi, A .
TETRAHEDRON LETTERS, 2001, 42 (45) :7975-7978
[6]  
Eynde J. J. V., 1997, HETEROCYCLES, V45, P1967
[7]   Researches on pyrimidines CXXXIV The reaction of phenylacetaldehyde and acetophenone with urea [J].
Folkers, K ;
Johnson, TB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :3361-3368
[8]   Researches on pyrimidines CXXX Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines [J].
Folkers, K ;
Harwood, HJ ;
Johnson, TB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1932, 54 :3751-3758
[9]   Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones [J].
Hu, EH ;
Sidler, DR ;
Dolling, UH .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3454-3457
[10]  
KAPPE CO, 1993, TETRAHEDRON, V49, P6937