p-TsOH promoted Fischer indole synthesis of multi-substituted 2-trifluoromethyl indole derivatives

被引：25

作者：

Jiang, Haizhen ^{[1
]}

Wang, Yangli ^{[1
]}

Wan, Wen ^{[1
,2
]}

Hao, Jian ^{[1
,2
]}

机构：

[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorme Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 14期

基金：

中国国家自然科学基金;

关键词：

Fluorinated indoles; Fluorinated ketoesters; Fischel indole synthesis; BEARING METHOXYCARBONYL; FLUORINE; ACCESS;

D O I：

10.1016/j.tet.2010.01.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A p-TsOH promoted one-pot synthesis of multi-substituted 2-trifluoromethyl indole derivatives, for instance, 2-trifluoromethy1-3-phenylindoles, 2-trifluoromethyl-indole-3-propanoates, and 2-trifluoromethyl-indole-3-butanoates from reactions of 1,1,1-traluoro-3-phenylacetone and simply prepared omega-trifluoromethyl substituted and epsilon-ketoesters with aryl hydrazines via Fischer indole synthesis has been developed (C) 2010 Elsevier Ltd All iights reserved

引用

页码：2746 / 2751

页数：6

共 37 条

[1] Elaboration of 2-(trifluoromethyl)indoles via a cascade coupling/condensation/deacylation process [J].

Chen, Yu ;

Wang, Yuji ;

Sun, Zheming ;

Ma, Dawei .

ORGANIC LETTERS, 2008, 10 (04) :625-628

[2] GENERATION AND REACTIONS OF TRIFLUOROACETIMIDOYL RADICALS [J].

DANOH, Y ;

MATTA, H ;

UEMURA, J ;

WATANABE, H ;

UNEYAMA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (05) :1497-1507

[3] Synthesis and antitumor activity of novel cyclopropapyrroloindole (CPI) derivatives bearing methoxycarbonyl and trifluoromethyl groups [J].

Fukuda, Y ;

Furuta, H ;

Shiga, F ;

Oomori, Y ;

Kusama, Y ;

Ebisu, H ;

Terashima, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (13) :1683-1688

[4] Novel seco cyclopropa[c]pyrrolo [3,2-e]indole bisalkylators bearing a 3,3′-arylenebisacryloyl group as a linker [J].

Fukuda, Y ;

Seto, S ;

Furuta, H ;

Ebisu, H ;

Oomori, Y ;

Terashima, S .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (09) :1396-1406

[5] Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups [J].

Fukuda, Y ;

Furuta, H ;

Kusama, Y ;

Ebisu, H ;

Oomori, Y ;

Terashima, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (08) :1448-1458

[6]

FURSTNER A, 1994, J ORG CHEM, V59, P5215

[7] Grignard cyclization reaction of fluorinated N-arylimidoyl chlorides:: A novel and facile access to 2-fluoroalkyl indoles [J].

Ge, Fenglian ;

Wang, Zengxue ;

Wan, Wen ;

Hao, Jian .

SYNLETT, 2007, (03) :447-450

[8] SYNTHESIS, CHEMISTRY, AND PHOTOCHEMICAL SUBSTITUTIONS OF 6,11-DIHYDRO-5H-PYRROLO[2,1-B][3]BENZAZEPIN-11-ONES [J].

GIRARD, Y ;

ATKINSON, JG ;

BELANGER, PC ;

FUENTES, JJ ;

ROKACH, J ;

ROONEY, CS ;

REMY, DC ;

HUNT, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (19) :3220-3234

[9]

Gribble G.W., 1996, COMPREHENSIVE HETERO, V2, P207, DOI DOI 10.1016/B978-008096518-5.00043-5

[10]

Harriman G. C. B., 2002, Patent, Patent No. [WO2002072549, 2002072549]

← 1 2 3 4 →