An efficient and environmentally friendly method for synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by Bi(NO3)3•5H2O

被引：52

作者：

Khodaei, MM ^{[1
]}

Khosropour, AR ^{[1
]}

Beygzadeh, M ^{[1
]}

机构：

[1] Razi Univ, Dept Chem, Kermanshah 67149, Iran

来源：

SYNTHETIC COMMUNICATIONS | 2004年 / 34卷 / 09期

关键词：

aldehydes; Lewis acids; catalysts; Biginelli; Bi(NO3)(3);

D O I：

10.1081/SCC-120030742

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bismuth nitrate pentahydrate catalyzes the three component condensation reaction of an aromatic aldehyde, urea and beta-ketoester or a beta-diketone under solvent-free conditions to afford the corresponding dihydropyrimidinones (DHPMs) in high yields. The present method is also effective for the selective condensation of aryl aldehydes in the presence of aliphatic aldehydes.

引用

收藏

页码：1551 / 1557

页数：7

相关论文

共 28 条

[1] 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

[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] A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate [J].

Bhatia, KA ;

Eash, KJ ;

Leonard, NM ;

Oswald, MC ;

Mohan, RS .

TETRAHEDRON LETTERS, 2001, 42 (46) :8129-8132

[4] 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

[5] Bismuth nitrate pentahydrate:: a new and environmentally benign reagent for guanidylation of N-benzoylthioureas [J].

Cunha, S ;

de Lima, BR ;

de Souza, AR .

TETRAHEDRON LETTERS, 2002, 43 (01) :49-52

[6]

Fan XS, 2002, J CHEM RES-S, P436

[7] PHARMACOLOGICAL PROFILE OF THE DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS SQ-32,547 AND SQ-32,946 [J].

GROVER, GJ ;

DZWONCZYK, S ;

MCMULLEN, DM ;

NORMANDIN, DE ;

PARHAM, CS ;

SLEPH, PG ;

MORELAND, S .

JOURNAL OF CARDIOVASCULAR PHARMACOLOGY, 1995, 26 (02) :289-294

[8] 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

[9]

Jin TS, 2002, J CHEM RES-S, P37

[10]

Kappe CO, 1997, TETRAHEDRON, V53, P2803