Polyphosphate ester-mediated synthesis of dihydropyrimidines. Improved conditions for the Biginelli reaction

被引:250
作者
Kappe, CO [1 ]
Falsone, SF [1 ]
机构
[1] Graz Univ, Inst Organ Chem, A-8010 Graz, Austria
关键词
Biginelli reaction; dihydropyrimidines; N-acyliminium ions; polyphosphate ester; calcium channel modulators;
D O I
10.1055/s-1998-1764
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dihydropyrimidines 7 are prepared in high yield by a one-pot condensation of aldehydes, acetoacetates, and ureas using a polyphosphate ester-mediated cyclocondensation reaction. Yields are significantly higher than utilizing classical Biginelli reaction conditions.
引用
收藏
页码:718 / 720
页数:3
相关论文
共 32 条
[1]  
[Anonymous], [No title captured]
[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]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[4]   SYNTHESIS OF CASEADINE METHYL ETHER [J].
CAVA, MP ;
LAKSHMIK.MV ;
MITCHELL, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2665-+
[5]   DIHYDROPYRIMIDINES - NOVEL CALCIUM-ANTAGONISTS WITH POTENT AND LONG-LASTING VASODILATIVE AND ANTIHYPERTENSIVE ACTIVITY [J].
CHO, H ;
UEDA, M ;
SHIMA, K ;
MIZUNO, A ;
HAYASHIMATSU, M ;
OHNAKA, Y ;
TAKEUCHI, Y ;
HAMAGUCHI, M ;
AISAKA, K ;
HIDAKA, T ;
KAWAI, M ;
TAKEDA, M ;
ISHIHARA, T ;
FUNAHASHI, K ;
SATOH, F ;
MORITA, M ;
NOGUCHI, T .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2399-2406
[6]  
DIXON LA, 1995, ENCY REAGENTS ORGANI, V6, P4166
[7]  
Ehsan A., 1967, PAKISTAN J SCI IND R, V10, P83
[8]   Ring conformation and ester orientation in dihydropyrimidinecarboxylates: a combined theoretical (ab initio, density functional) and X-ray crystallographic study [J].
Fabian, WMF ;
Semones, MA ;
Kappe, CO .
THEOCHEM-JOURNAL OF MOLECULAR STRUCTURE, 1998, 432 (03) :219-228
[9]   Researches on pyrimidines CXXXIII Some reactions and derivatives of 2-keto-4-phenyl-5-carbethoxy-6-methyl-1,2,3,4-tetrahydropyrimidine [J].
Folkers, K ;
Johnson, TB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :2886-2893
[10]   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