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

被引：56

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
Arcadi, Antonio
[J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3266 - 3325
[2] An Enzymatic Cyclopentyl[b]indole Formation Involved in Scytonemin Biosynthesis
Balskus, Emily P.
Walsh, Christopher T.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) : 14648 - +
[3] Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds
Bandini, Marco
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) : 1358 - 1367
[4] Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles
Bandini, Marco
Eichholzer, Astrid
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) : 9533 - 9537
[5] Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids
Banwell, Martin G.
Ma, Xinghua
Taylor, Rebecca M.
Willis, Anthony C.
[J]. ORGANIC LETTERS, 2006, 8 (21) : 4959 - 4961
[6] Gold: a relatively new catalyst
Bond, GC
[J]. CATALYSIS TODAY, 2002, 72 (1-2) : 5 - 9
[7] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
Cacchi, S
Fabrizi, G
[J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
[8] Electronic Effect Directed Au(I)-Catalyzed Cyclic C2-H Bond Functionalization of 3-Allenylindoles
Chen, Bo
Fan, Wu
Chai, Guobi
Ma, Shengming
[J]. 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
Chowdhury, Chinmay
Das, Bimolendu
Mukherjee, Sanjukta
Achari, Basudeb
[J]. 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
Churruca, Fatima
Fousteris, Manolis
Ishikawa, Yuichi
Rekowski, Margarete von Wantoch
Hounsou, Candide
Surrey, Thomas
Giannis, Athanassios
[J]. ORGANIC LETTERS, 2010, 12 (09) : 2096 - 2099

← 1 2 3 4 5 6 7 →