A new substrate for the Biginelli cyclocondensation:: Direct preparation of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones from a β-keto carboxylic acid

被引:117
作者
Bussolari, JC [1 ]
McDonnell, PA [1 ]
机构
[1] RW Johnson Pharmaceut Res Inst, Raritan, NJ 08869 USA
关键词
D O I
10.1021/jo005512a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:6777 / 6779
页数:3
相关论文
共 24 条
[1]  
[Anonymous], 1978, TRANSITION STATES BI
[2]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS - 2-HETEROSUBSTITUTED 4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
SCHWARTZ, J ;
MORELAND, S ;
HEDBERG, A ;
GOUGOUTAS, JZ ;
MALLEY, MF ;
FLOYD, DM .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1510-1515
[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]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[5]  
COOPER K, Patent No. 11281
[6]   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
[7]   Application of the tethered Biginelli reaction for enantioselective synthesis of batzelladine alkaloids. Absolute configuration of the tricyclic guanidine portion of batzelladine B [J].
Franklin, AS ;
Ly, SK ;
Mackin, GH ;
Overman, LE ;
Shaka, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1512-1519
[8]   Solid phase synthesis of dihydropyrimidinones and pyrimidinone carboxylic acids from malonic acid resin [J].
Hamper, BC ;
Gan, KZ ;
Owen, TJ .
TETRAHEDRON LETTERS, 1999, 40 (27) :4973-4976
[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]  
Johnson T.B., 1933, J AM CHEM SOC, V55, P3784, DOI DOI 10.1021/JA01336A054