One-Pot Synthesis of Indole-3-acetic Acid Derivatives through the Cascade Tsuji-Trost Reaction and Heck Coupling

被引：19

作者：

Chen, Dongsheng ^{[1
,2
]}

Chen, Yuanyuan ^{[1
,2
]}

Ma, Zhilong ^{[1
,2
]}

Zou, Lei ^{[1
,2
]}

Li, Jianqi ^{[1
,2
]}

Liu, Yu ^{[1
,2
]}

机构：

[1] China State Inst Pharmaceut Ind, Novel Technol Ctr Pharmaceut Chem, Shanghai Inst Pharmaceut Ind, 285 Gebaini Rd, Shanghai 201203, Peoples R China

[2] China State Inst Pharmaceut Ind, Shanghai Engn Res Ctr Pharmaceut Proc, Shanghai Inst Pharmaceut Ind, 285 Gebaini Rd, Shanghai 201203, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 12期

关键词：

SUBSTITUTED INDOLES; PALLADIUM; HETEROCYCLES; SYSTEMS; ACIDS; ARYL; CONSTRUCTION; CYCLIZATION; AZAINDOLES; PLATFORM;

D O I：

10.1021/acs.joc.8b01056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical palladium-mediated cascade Tsuji- Trost reaction/Heck coupling of N-Ts o-bromoanilines with 4-acetoxy-2-butenonic acid derivatives using a Pd(OAc)(2)/P(o-tol)(3)/DIPEA system is described for a straightforward synthesis of indole-3-acetic acid derivatives. This methodology was successfully applied to synthesize various substituted indole/azaindole-3-acetic acid derivatives and Almotriptan, which is a drug for the acute treatment of migraines. Moreover, a plausible cyclization mechanism has been proposed.

引用

页码：6805 / 6814

页数：10

共 51 条

[1] Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles [J].

Alex, Karolin ;

Tillack, Annegret ;

Schwarz, Nicolle ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2304-2307

[2] Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles [J].

Arisawa, Mitsuhiro ;

Terada, Yukiyoshi ;

Takahashi, Kazuyuki ;

Nakagawa, Masako ;

Nishida, Atsushi .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) :4255-4261

[3] N-(2-Bromophenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzenesulfonamide [J].

Arshad, Muhammad Nadeem ;

Khan, Islam Ullah ;

Holman, K. Travis ;

Asiri, Abdullah M. ;

Rafique, H. M. .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 :O2356-U467

[4] Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].

Barluenga, Jose ;

Rodriguez, Felix ;

Fananas, Francisco J. .

CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048

[5] First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems [J].

Beller, M ;

Fischer, H ;

Kuhlein, K ;

Reisinger, CP ;

Herrmann, WA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 520 (1-2) :257-259

[6] Synthesis of 5-(sulfamoylmethyl)indoles [J].

Bosch, J ;

Roca, T ;

Armengol, M ;

Fernández-Forner, D .

TETRAHEDRON, 2001, 57 (06) :1041-1048

[7]

BREDT AB, 1982, CANCER, V50, P1430, DOI 10.1002/1097-0142(19821001)50:7<1430::AID-CNCR2820500732>3.0.CO

[8]

2-U

[9] SYNTHESES OF SOME SUBSTITUTED INDOLE-3-ACETIC ACIDS [J].

BULLOCK, MW ;

HAND, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (22) :5852-5854

[10] A general synthesis of substituted indoles from cyclic enol ethers and enol lactones [J].

Campos, KR ;

Woo, JCS ;

Lee, S ;

Tillyer, RD .

ORGANIC LETTERS, 2004, 6 (01) :79-82

← 1 2 3 4 5 6 →