L-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines

被引：51

作者：

Jiang, Huanfeng ^{[1
]}

Mai, Ronghuan ^{[1
]}

Cao, Hua ^{[1
]}

Zhu, Qiuhua ^{[1
]}

Liu, Xiaohang ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 23期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; 3-COMPONENT DOMINO SYNTHESIS; MULTICOMPONENT REACTIONS; HANTZSCH REACTION; REDUCTIVE AMINATION; POLYHYDROQUINOLINE DERIVATIVES; MANNICH REACTION; ALDER REACTIONS; ALDOL REACTIONS; IONIC LIQUID;

D O I：

10.1039/b914659h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly functionalized multisubstituted 1,4-dihydropyridines 5 have been concisely synthesized in moderate to good yields via L-proline-catalyzed one-pot multicomponent reactions (MCRs) of alkynoates or alkynones 1, amines 2, beta-dicarbonyl compounds 3 and aldehydes 4 under mild conditions. The MCR process involves hydroamination/Knoevenagel condensation/Michael-type addition/intramolecular cyclization processes and leads to the formation of 1,4-dihydropyridines 5. The molecular structure of 5ckaa was confirmed by single-crystal X-ray diffraction. This method is energy saving and environmentally friendly, providing easy access to diverse multisubstituted polyfunctional 1,4-dihydropyridines.

引用

页码：4943 / 4953

页数：11

共 79 条

[1] Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media
Abdolmohammadi, Shahrzad
Balalaie, Saeed
[J]. TETRAHEDRON LETTERS, 2007, 48 (18) : 3299 - 3303
[2] Solid supported synthesis of structurally diverse dihydropyrido[2,3-d]pyrimidines using microwave irradiation
Agarwal, A
Chauhan, PMS
[J]. TETRAHEDRON LETTERS, 2005, 46 (08) : 1345 - 1348
[3] The proline-catalyzed asymmetric Amination of branched aldehydes
Baumann, Thomas
Vogt, Henning
Braese, Stefan
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (02) : 266 - 282
[4] Boer Rainer, 1995, Drugs of the Future, V20, P499
[5] BOEVIG A, 2004, ANGEW CHEM INT EDIT, V43, P1109
[6] Bossert F., 1981, ANGEW CHEM-GER EDIT, V93, P755
[7] Bretzel R.G., 1992, DRUGS PUT, V17, P465
[8] BRETZEL RG, 1993, AM J KIDNEY DIS, V21, P53
[9] Magnesium nitride as a convenient source of ammonia: Preparation of dihydropyridines
Bridgwood, Katy L.
Veitch, Gemma E.
Ley, Steven V.
[J]. ORGANIC LETTERS, 2008, 10 (16) : 3627 - 3629
[10] Synthesis of 1,2-dihydropyridines using vinyloxiranes as masked dienolates in imino-aldol reactions
Brunner, Bernhard
Stogaitis, Nicole
Lautens, Mark
[J]. ORGANIC LETTERS, 2006, 8 (16) : 3473 - 3476

← 1 2 3 4 5 6 7 8 →