The first proline-catalyzed Friedlander annulation: Regioselective synthesis of 2-substituted quinoline derivatives

被引:40
作者
Jiang, Biao [1 ]
Dong, Jia-jia [1 ]
Jin, Yun [1 ]
Du, Xiao-long [1 ]
Xu, Min [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
关键词
aldol reactions; quinoline; cyclization; proline;
D O I
10.1002/ejoc.200800121
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first proline-catalyzed Friedlander annulation for the synthesis of 2-substituted 4-trifluoromethyl quinoline derivatives is described. Excellent re gio selectivity as well as good yields were shown in a variety of cases, and a tandem aldol-cyclization pathway might be involved. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码:2693 / 2696
页数:4
相关论文
共 36 条
[1]  
[Anonymous], 2008, EUR J ORG CHEM
[2]  
Chambers RD, 1997, TOP CURR CHEM, V192, P1
[3]  
CHENG CC, 1982, ORG REACTIONS, V28, P37
[4]   A rhodium-catalyzed route for oxidative coupling and cyclization of 2-aminobenzyl alcohol with ketones leading to quinolines [J].
Cho, CS ;
Seok, HJ ;
Shim, SC .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (06) :1219-1222
[5]   Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
CHEMICAL COMMUNICATIONS, 2001, (24) :2576-2577
[6]   Synthesis of 2-substituted trifluoromethylquinolines for the evaluation of leishmanicidal activity [J].
Dade, J ;
Provot, O ;
Moskowitz, H ;
Mayrargue, J ;
Prina, E .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (04) :480-483
[7]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[8]   Regioselectivity of Friedlander quinoline syntheses [J].
Diedrich, Claas Lueder ;
Haase, Detlev ;
Saak, Wolfgang ;
Christoffers, Jens .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (10) :1811-1816
[9]   Highly regioselective Friedlander annulations with unmodified ketones employing novel amine catalysts: Syntheses of 2-substituted quinolines, 1,8-naphthyridines, and related heterocycles [J].
Dormer, PG ;
Eng, KK ;
Farr, RN ;
Humphrey, GR ;
McWilliams, JC ;
Reider, PJ ;
Sager, JW ;
Volante, RP .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :467-477
[10]   Friedlander synthesis of chiral alkyl-substituted 1,10-phenanthrolines [J].
Gladiali, S ;
Chelucci, G ;
Mudadu, MS ;
Gastaut, MA ;
Thummel, RP .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :400-405