Synthesis of 2-Aminoindoles through Gold-Catalyzed C-H Annulations of Sulfilimines with N-Arylynamides

被引：58

作者：

Tian, Xianhai ^{[1
]}

Song, Lina ^{[1
]}

Rudolph, Matthias ^{[1
]}

Rominger, Frank ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 11期

关键词：

FORMAL 3+2 CYCLOADDITION; NUCLEOPHILIC NITRENOIDS; 2-ALKYNYL ARYLAZIDES; SELECTIVE SYNTHESIS; ACCESS; YNAMIDES; CARBENES; ALKYNES; FUNCTIONALIZATION; DERIVATIVES;

D O I：

10.1021/acs.orglett.9b01501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new gold-catalyzed C-H annulation of sulfilimines with N-phenylynamides is presented. As key intermediates of this operationally simple reaction, the in situ generated a-imino gold carbenes insert into the ortho C-H bonds of the phenyl groups to afford 2-aminoindoles bearing a variety of substitution patterns in high selectivities. This reaction offers a facile approach to biologically important 2-aminoindoles by using inexpensive and readily available starting materials.

引用

页码：4327 / 4330

页数：4

共 92 条

[1] Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates Dedicated to Professor Dr Julius Rebek, Jr. on the occasion of his 75th birthday. [J].

Aguilar, Enrique ;

Santamaria, Javier .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (09) :1513-1540

[2] Regiodivergent Control in the Gold(I) Catalyzed Synthesis of 7-Pyrazolylindoles from 1-Propargyl-1H-benzotriazoles and Ynamides through α-Imino Gold(I) Carbene Complexes [J].

Allegue, Dario ;

Gonzalez, Jairo ;

Fernandez, Sergio ;

Santamaria, Javier ;

Ballesteros, Alfredo .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (04) :758-768

[3]

[Anonymous], 2015, SYNTHESIS

[4] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[5] Synthesis and antiproliferative activity of [1,2,3,5]tetrazino-[5,4-a]indoles, a new class of azolo-tetrazinones [J].

Barraja, P ;

Diana, P ;

Lauria, A ;

Montalbano, A ;

Almerico, AM ;

Dattolo, G ;

Cirrincione, G .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (02) :295-300

[6] Gold-Catalyzed Oxidative Cyclizations of cis-3-En-1-ynes To Form Cyclopentenone Derivatives [J].

Bhunia, Sabyasachi ;

Ghorpade, Satish ;

Huple, Deepak B. ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) :2939-2942

[7] Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo .

CHEMICAL REVIEWS, 2011, 111 :PR215-PR283

[8] Metal-Free Oxidation/C(sp3)-H Functionalization of Unactivated Alkynes Using Pyridine-N-Oxide as the External Oxidant [J].

Chen, Dian-Feng ;

Han, Zhi-Yong ;

He, Yu-Ping ;

Yu, Jie ;

Gong, Liu-Zhu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (49) :12307-12310

[9] Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: highly efficient synthesis of functionalized oxazoles [J].

Chen, Ming ;

Sun, Ning ;

Chen, Haoyi ;

Liu, Yuanhong .

CHEMICAL COMMUNICATIONS, 2016, 52 (37) :6324-6327

[10] Nucleophilic Nitrenoids Through π-Acid Catalysis: Providing a Common Basis for Rapid Access into Diverse Nitrogen Heterocycles [J].

Davies, Paul W. ;

Garzon, Miguel .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (08) :694-708

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