Synthesis of polysubstituted cyclopenta[b] indoles via relay gold(I)/Bronsted acid catalysis

被引：57

作者：

Dhiman, Seema ^{[1
]}

Ramasastry, S. S. V. ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, SAS Nagar 140306, Punjab, India

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 03期

关键词：

NONREARRANGED MONOTERPENOID UNIT; SIMPLE INDOLE ALKALOIDS; ONE-POT SYNTHESIS; BOND FUNCTIONALIZATION; GOLD CATALYSIS; ALCOHOLS; ACCESS; CYCLOISOMERIZATION; INDOLODITERPENES; KETONES;

D O I：

10.1039/c4cc08174a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient relay catalytic process involving Au(I)/ Bronsted acid to access various polysubstituted cyclopentannulated indoles from easily accessible 1-(2-aminophenyl) prop-2-ynols and readily available 1,3-dicarbonyls has been developed. In an unprecedented event, the intermediate 2-indolylmethyl cations undergo the cation-Ene reaction with various 1,3-dicarbonyls followed by an intramolecular FriedelCrafts- type reaction generating functionalized cyclopenta[b] indoles.

引用

页码：557 / 560

页数：4

共 64 条

[1] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[2] An Enzymatic Cyclopentyl[b]indole Formation Involved in Scytonemin Biosynthesis [J].

Balskus, Emily P. ;

Walsh, Christopher T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) :14648-+

[3] Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds [J].

Bandini, Marco .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) :1358-1367

[4] Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9533-9537

[5] Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids [J].

Banwell, Martin G. ;

Ma, Xinghua ;

Taylor, Rebecca M. ;

Willis, Anthony C. .

ORGANIC LETTERS, 2006, 8 (21) :4959-4961

[6] Gold: a relatively new catalyst [J].

Bond, GC .

CATALYSIS TODAY, 2002, 72 (1-2) :5-9

[7] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[8] Electronic Effect Directed Au(I)-Catalyzed Cyclic C2-H Bond Functionalization of 3-Allenylindoles [J].

Chen, Bo ;

Fan, Wu ;

Chai, Guobi ;

Ma, Shengming .

ORGANIC LETTERS, 2012, 14 (14) :3616-3619

[9] Palladium-Catalyzed Approach for the General Synthesis of (E)-2-Arylmethylidene-N-tosylindolines and (E)-2-Arylmethylidene-N-tosyl/nosyltetrahydroquinolines: Access to 2-Substituted Indoles and Quinolines [J].

Chowdhury, Chinmay ;

Das, Bimolendu ;

Mukherjee, Sanjukta ;

Achari, Basudeb .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11) :5108-5119

[10] A Novel Approach to Indoloditerpenes by Nazarov Photocyclization: Synthesis and Biological Investigations of Terpendole E Analogues [J].

Churruca, Fatima ;

Fousteris, Manolis ;

Ishikawa, Yuichi ;

Rekowski, Margarete von Wantoch ;

Hounsou, Candide ;

Surrey, Thomas ;

Giannis, Athanassios .

ORGANIC LETTERS, 2010, 12 (09) :2096-2099

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