Towards the synthesis of C-glycosylated dihydropyrimidine libraries via the three-component Biginelli reaction.: A novel approach to artificial nucleosides

被引：37

作者：

Dondoni, A ^{[1
]}

Massi, A ^{[1
]}

Sabbatini, S ^{[1
]}

机构：

[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 27期

关键词：

Biginelli reaction; dihydropyrimidines; C-glycosides; multicomponent reaction;

D O I：

10.1016/S0040-4039(01)00769-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis acid catalyzed (BF3. Et2O, CuCl, AcOH) one-pot three-component cyclocondensation of urea with C-glycosylated aldehydes and beta -keto esters (Biginelli reaction) in a combinatorial manner afforded three different series of 3,4-dihydropyrimidin-2(1H)-ones bearing C-glycosyl moieties at C4, C6, and at both C4 and C6. (C) 2001 Elsevier Science Ltd. AH rights reserved.

引用

页码：4495 / 4497

页数：3

共 25 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
ATWAL, KS
SWANSON, BN
UNGER, SE
FLOYD, DM
MORELAND, S
HEDBERG, A
OREILLY, BC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) : 806 - 811
[2] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .2. 3-SUBSTITUTED-4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES
ATWAL, KS
ROVNYAK, GC
KIMBALL, SD
FLOYD, DM
MORELAND, S
SWANSON, BN
GOUGOUTAS, JZ
SCHWARTZ, J
SMILLIE, KM
MALLEY, MF
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) : 2629 - 2635
[3] Chu C.K., 1993, Nucleosides and Nucleotides as Antitumor and Antiviral Agents
[4] SUGAR BETA-KETOESTERS - NEW CHIRONS IN THE SYNTHESIS OF 6-DEOXYHEPTULOSURONO-7,4-LACTONES
DHAVALE, DD
BHUJBAL, NN
JOSHI, P
DESAI, SG
[J]. CARBOHYDRATE RESEARCH, 1994, 263 (02) : 303 - 307
[5] Formylation of carbohydrates and the evolution of synthetic routes to artificial oligosaccharides and glycoconjugates
Dondoni, A
[J]. PURE AND APPLIED CHEMISTRY, 2000, 72 (09) : 1577 - 1588
[6] THIAZOLE-BASED SYNTHESIS OF FORMYL C-GLYCOSIDES
DONDONI, A
SCHERRMANN, MC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6404 - 6412
[7] DONDONI A, UNPUB TETRAHEDRON
[8] FERNANDEZ MV, 1988, HETEROCYCLES, V27, P2133
[9] FERNANDEZ MV, 1986, HETEROCYCLES, V24, P679
[10] 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

← 1 2 3 →