New Approaches to Nitrogen Containing Heterocycles: Enantioselective Organocatalyzed Synthesis of Dihydropyridines (DHP's), Quinolizidine Derivatives and Dihydropyrimidines (DHPM's)

被引:0
作者
Hoai Thu Pham [1 ]
Chataigner, Isabelle [2 ]
Renaud, Jean-Luc [1 ]
机构
[1] Univ Caen ENSICAEN, UMR CNRS LCMT 6507, F-14050 Caen, France
[2] Univ Rouen, UMR CNRS COBRA 6014, F-76821 Mont St Aignan, France
关键词
Dihydropyridines; Dihydropyrimidines; Quinolizidines; Chiral Bronsted acids; Chiral thioureas; Proline type derivatives; CALCIUM-CHANNEL BLOCKERS; SOLVENT-FREE CONDITIONS; BETA-ENAMINO ESTERS; ONE-POT SYNTHESIS; BIGINELLI REACTION; BRONSTED ACID; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; PICTET-SPENGLER; ALPHA; BETA-UNSATURATED ALDEHYDES;
D O I
10.2174/138527212802651322
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrogen-containing heterocycles, and more specifically the chiral ones, possess various biological and pharmaceutical properties. Among the approaches to these compounds, the organocatalyzed asymmetric multicomponent reaction has emerged as a powerful tool. This review will focus on the later development to chiral dihydropyridines, dihydropyrimidines and quinolizidines via asymmetric organocatalyzed synthesis.
引用
收藏
页码:1754 / 1775
页数:22
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共 119 条
[1]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[2]   An asymmetric synthesis of a 4-substituted-1,4-dihydropyridine [J].
Ashworth, I ;
Hopes, P ;
Levin, D ;
Patel, I ;
Salloo, R .
TETRAHEDRON LETTERS, 2002, 43 (28) :4931-4933
[3]   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
[4]   In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective α1A receptor antagonists for the treatment of benign prostatic hyperplasia [J].
Barrow, JC ;
Nantermet, PG ;
Selnick, HG ;
Glass, KL ;
Rittle, KE ;
Gilbert, KF ;
Steele, TG ;
Homnick, CF ;
Freidinger, RM ;
Ransom, RW ;
Kling, P ;
Reiss, D ;
Broten, TP ;
Schorn, TW ;
Chang, RSL ;
O'Malley, SS ;
Olah, TV ;
Ellis, JD ;
Barrish, A ;
Kassahun, K ;
Leppert, P ;
Nagarathnam, D ;
Forray, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (14) :2703-2718
[5]   Organocatalysis-after the gold rush [J].
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189
[6]   Searching for balanced hybrid NO-donor 1,4-dihydropyridines with basic properties [J].
Boschi, D ;
Caron, G ;
Visentin, S ;
Di Stilo, A ;
Rolando, B ;
Fruttero, R ;
Gasco, A .
PHARMACEUTICAL RESEARCH, 2001, 18 (07) :987-991
[7]   Asymmetric Aza-[3+3] Annulation in the Synthesis of Indolizidines: An Unexpected Reversal of Regiochemistry [J].
Buchanan, Grant S. ;
Dai, Huifang ;
Hsung, Richard P. ;
Gerasyuto, Aleksey I. ;
Scheinebeck, Casi M. .
ORGANIC LETTERS, 2011, 13 (16) :4402-4405
[8]   Cooperative and Enantioselective NbCl5/Primary Amine Catalyzed Biginelli Reaction [J].
Cai, Yong-Feng ;
Yang, Hua-Meng ;
Li, Li ;
Jiang, Ke-Zhi ;
Lai, Guo-Qiao ;
Jiang, Jian-Xiong ;
Xu, Li-Wen .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (26) :4986-4990
[9]   Highly enantioselective organocatalytic Biginelli reaction [J].
Chen, Xiao-Hua ;
Xu, Xiao-Ying ;
Liu, Hua ;
Cun, Lin-Feng ;
Gong, Liu-Zhu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14802-14803
[10]   The development of asymmetric primary amine catalysts based on cinchona alkaloids [J].
Chen, Ying-Chun .
SYNLETT, 2008, (13) :1919-1930