Synthesis of Indoles via Electron-Catalyzed Intramolecular C-N Bond Formation

被引：23

作者：

Bugaenko, Dmitry I. ^{[1
]}

Dubrovina, Anastasia A. ^{[1
]}

Yurovskaya, Marina A. ^{[1
]}

Karchava, Alexander V. ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119234, Russia

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 23期

关键词：

METAL-FREE SYNTHESIS; H ACTIVATION; MULTISUBSTITUTED INDOLES; AMINATION; HETEROCYCLES; DERIVATIVES; ANNULATION; IDENTIFICATION; ALKALOIDS; MECHANISM;

D O I：

10.1021/acs.orglett.8b02784

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new protocol for the preparation of N-substituted indole-3-carboxylates has been developed. The key C-N bond formation occurs under transition-metal-free conditions employing a t-BuOK/DMF system without special initiators or additives. Across a number of substrates, indoles were afforded in yields higher or comparable to those obtained under transition-metal catalyzed conditions. While demonstrating high functional group tolerance, new conditions are particularly attractive for manufacturing halogenated indoles that cannot be made in a pure form using other metal-based catalytic methods.

引用

页码：7358 / 7362

页数：5

共 71 条

[31] Electron-Catalyzed Coupling of Magnesium Amides with Aryl Iodides [J].

Kiriyama, Kazuya ;

Okura, Keisho ;

Tamakuni, Fumiko ;

Shirakawa, Eiji .

CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (18) :4519-4522

[32] Copper-Catalyzed Synthesis of lndoles and Related Heterocycles in Renewable Solvents [J].

Koenig, Stefan G. ;

Dankwardt, John W. ;

Liu, Yanbing ;

Zhao, Hang ;

Singh, Surendra P. .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (06) :1359-1363

[33] Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles [J].

Kumar, S. Vijay ;

Saraiah, B. ;

Parameshwarappa, G. ;

Ila, H. ;

Verma, Girijesh K. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) :7961-7978

[34] Copper-Catalyzed Synthesis of Multisubstituted Indoles through Tandem Ullmann-Type C-N Formation and Cross-dehydrogenative Coupling Reactions [J].

Li, Yue ;

Peng, Jinsong ;

Chen, Xin ;

Mo, Baichuan ;

Li, Xue ;

Sun, Peng ;

Chen, Chunxia .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (09) :5288-5294

[35] Copper-catalyzed N-alkylation of indoles by N-tosylhydrazones [J].

Ling, Li ;

Cao, Jing ;

Hu, Jianfeng ;

Zhang, Hao .

RSC ADVANCES, 2017, 7 (45) :27974-27980

[36]

Magano J, 2013, TRANSITION METAL-CATALYZED COUPLINGS IN PROCESS CHEMISTRY: CASE STUDIES FROM THE PHARMACEUTICAL INDUSTRY, P1

[37] Resonating valence bond ground state in oxygen-functionalized phenalenyl-based neutral radical molecular conductors [J].

Mandal, SK ;

Samanta, S ;

Itkis, ME ;

Jensen, DW ;

Reed, RW ;

Oakley, RT ;

Tham, FS ;

Donnadieu, B ;

Haddon, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1982-1994

[38] Identification of indole derivatives exclusively interfering with a G protein-independent signaling pathway of the prostaglandin D2 receptor CRTH2 [J].

Mathiesen, JM ;

Ulven, T ;

Martini, L ;

Gerlach, LO ;

Heinemann, A ;

Kostenis, E .

MOLECULAR PHARMACOLOGY, 2005, 68 (02) :393-402

[39] FERRIC CHLORIDE-CATALYZED SYNTHESIS OF INDOLES USING THE INTRAMOLECULAR AMINATION OF ARYL BROMIDES [J].

Melkonyan, F. S. ;

Topolyan, A. P. ;

Karchava, A. V. ;

Yurovskaya, M. A. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (09) :1158-1160

[40] Simple synthesis of methyl 1-(1,1-dimethyl-prop-2-en-1-yl)-1h-indole-3-carboxylate [J].

Melkonyan, F. S. ;

Topolyan, A. P. ;

Karchava, A. V. ;

Yurovskaya, M. A. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (10) :1288-1290

← 1 2 3 4 5 6 7 8 →