Efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones over silica sulfuric acid as a reusable catalyst under solvent-free conditions

被引：55

作者：

Salehi, P

Dabiri, M

Zolfigol, MA

Ali, M

Fard, B

机构：

[1] Shahid Beheshti Univ, Dept Phytochem Aromat & Med Plants, Tehran, Iran

[2] Shahid Beheshti Univ Med Sci, Inst Drug Res, Tehran, Iran

[3] Shahid Beheshti Univ, Fac Sci, Dept Chem, Tehran 1983963113, Iran

[4] Bu Ali Sina Univ, Fac Sci, Dept Chem, Hamadan 65174, Iran

来源：

HETEROCYCLES | 2003年 / 60卷 / 11期

关键词：

D O I：

10.3987/COM-03-9837

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,4-Dihydropyrimidin-2(1H)-ones and their sulfur analogues are efficiently synthesized by the three-component condensation of beta-dicarbonyl compounds, aromatic and aliphatic aldehydes, and urea or thiourea in the presence of catalytic amounts of silica sulfuric acid under solvent-free conditions in high yields. The catalyst is recyclable and can be used several times without any decrease in the products yields.

引用

收藏

页码：2435 / 2440

页数：6

相关论文

共 36 条

[1]

ATWAL KS, 1987, HETEROCYCLES, V26, P1189

[2] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .3. 3-CARBAMOYL-4-ARYL-1,2,3,4-TETRAHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS ORALLY EFFECTIVE ANTIHYPERTENSIVE AGENTS [J].

ATWAL, KS ;

SWANSON, BN ;

UNGER, SE ;

FLOYD, DM ;

MORELAND, S ;

HEDBERG, A ;

OREILLY, BC .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :806-811

[3] 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

[4] 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

[5] 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

[6]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[7]

Falsone FS, 2001, ARKIVOC, V2, P1111

[8] Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction [J].

Fu, NY ;

Yuan, YF ;

Cao, Z ;

Wang, SW ;

Wang, JT ;

Peppe, C .

TETRAHEDRON, 2002, 58 (24) :4801-4807

[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] Synthesis and reactions of Biginelli compounds, part 19 - X-ray structure, conformational analysis, enantioseparation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol [J].

Kappe, CO ;

Shishkin, OV ;

Uray, G ;

Verdino, P .

TETRAHEDRON, 2000, 56 (13) :1859-1862

← 1 2 3 4 →