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

被引：282

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

页码：466 / 470

页数：5

共 33 条

[1] SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES
ATWAL, KS
ROVNYAK, GC
OREILLY, BC
SCHWARTZ, J
[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
Christoffers, J
[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
Dondoni, A
Massi, A
[J]. 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
Folkers, K
Johnson, TB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 : 3361 - 3368
[8] Researches on pyrimidines CXXX Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines
Folkers, K
Harwood, HJ
Johnson, TB
[J]. 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
Hu, EH
Sidler, DR
Dolling, UH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) : 3454 - 3457
[10] KAPPE CO, 1993, TETRAHEDRON, V49, P6937

← 1 2 3 4 →