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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 16期

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

页码：2693 / 2696

页数：4

共 36 条

[11]

Hiyama T., 2000, ORGANOFLUORINE COMPO, DOI DOI 10.1007/978-3-662-04164-2

[12] Friedlander approach for the incorporation of 6-bromoquinoline into novel chelating ligands [J].

Hu, YZ ;

Zhang, D ;

Thummel, RP .

ORGANIC LETTERS, 2003, 5 (13) :2251-2253

[13] Zn(II)-mediated alkynylation-cyclization of o-trifluoroacetyl anilines:: One-pot synthesis of 4-trifluoromethyl-substituted quinoline derivatives [J].

Jiang, B ;

Si, YG .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9449-9451

[14]

Jones G., 1977, CHEM HETEROCYCLIC 1, V32, P181

[15] 4-(trifluoromethyl)quinoline derivatives [J].

Lefebvre, O ;

Marull, M ;

Schlosser, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (11) :2115-2121

[16] REGIOSELECTIVE SYNTHESIS OF TRIFLUOROMETHYL SUBSTITUTED QUINOLINES FROM TRIFLUOROACETYL ACETYLENES [J].

LINDERMAN, RJ ;

KIROLLOS, KS .

TETRAHEDRON LETTERS, 1990, 31 (19) :2689-2692

[17] Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents [J].

List, B .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :548-557

[18]

MANSKE RHF, 1953, ORG REACTIONS, V7, P59

[19] RuCl2(dmso)4 catalyzes the solvent-free indirect Friedlander synthesis of polysubstituted quinolines from alcohols [J].

Martinez, Ricardo ;

Ramon, Diego J. ;

Yus, Miguel .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (10) :1599-1605

[20] A mild and efficient one-step synthesis of quinolines [J].

McNaughton, BR ;

Miller, BL .

ORGANIC LETTERS, 2003, 5 (23) :4257-4259

← 1 2 3 4 →