Catalyst-Controlled Chemodivergent Modification of Indoles with 2-Furylcarbinols: Piancatelli Reaction vs Cross-Dehydrative Coupling Reaction

被引：26

作者：

Xu, Jianfeng ^{[1
]}

Luo, Yi ^{[1
]}

Xu, Huaping ^{[1
]}

Chen, Zhengkai ^{[1
]}

Miao, Maozhong ^{[1
]}

Ren, Hongjun ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 07期

基金：

中国国家自然科学基金;

关键词：

FRIEDEL-CRAFTS REACTION; STEREOSELECTIVE-SYNTHESIS; PRIVILEGED STRUCTURES; FURFURYL CATIONS; DRUG DISCOVERY; REARRANGEMENT; DERIVATIVES; ALKYLATION; ALKALOIDS; ACID;

D O I：

10.1021/acs.joc.7b00090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A divergent synthetic strategy to functionalize the indole nucleus with readily available 2-furylcarbinols was developed: It was found that the 3-(4-oxa-2-cyclopentenyl)indoles were obtained in moderate to good yields (up to 89%),through Piancatelli reaction catalyzed by ZnCl2, whereas,employment of Bronsted acid TEA afforded directly coupled product 3-(2-furyl)incloles in moderate to good yields (up-to 87%) via the deprotonation rearomatization route.

引用

页码：3561 / 3570

页数：10

共 59 条

[1] Highly enantioselective Friedel-Crafts alkylations of indoles with simple enones catalyzed by zirconium(IV)-BINOL complexes [J].

Blay, Gonzalo ;

Fernandez, Isabel ;

Pedro, Jose R. ;

Vila, Carlos .

ORGANIC LETTERS, 2007, 9 (13) :2601-2604

[2] A synthesis strategy yielding skeletally diverse small molecules combinatorially [J].

Burke, MD ;

Berger, EM ;

Schreiber, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) :14095-14104

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

Cacchi, Sandro ;

Fabrizi, Giancarlo .

CHEMICAL REVIEWS, 2011, 111 :PR215-PR283

[4]

Cai Y., 2016, ANGEW CHEM INT EDIT, V55, P1

[5] Tandem Reaction Progress Analysis as a Means for Dissecting Catalytic Reactions: Application to the Aza-Piancatelli Rearrangement [J].

Chung, Ryan ;

Yu, Diana ;

Thai, Van T. ;

Jones, Alyssa F. ;

Veits, Gesine K. ;

de Alaniz, Javier Read ;

Hein, Jason E. .

ACS CATALYSIS, 2015, 5 (08) :4579-4585

[6] From Nature to Drug Discovery: The Indole Scaffold as a 'Privileged Structure' [J].

de Sa Alves, Fernando Rodrigues ;

Barreiro, Eliezer J. ;

Manssour Fraga, Carlos Alberto .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2009, 9 (07) :782-793

[7] Taming furfuryl cations for the synthesis of privileged structures and novel scaffolds [J].

Dhiman, Seema ;

Ramasastry, S. S. V. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (26) :4299-4303

[8] METHODS FOR DRUG DISCOVERY - DEVELOPMENT OF POTENT, SELECTIVE, ORALLY EFFECTIVE CHOLECYSTOKININ ANTAGONISTS [J].

EVANS, BE ;

RITTLE, KE ;

BOCK, MG ;

DIPARDO, RM ;

FREIDINGER, RM ;

WHITTER, WL ;

LUNDELL, GF ;

VEBER, DF ;

ANDERSON, PS ;

CHANG, RSL ;

LOTTI, VJ ;

CERINO, DJ ;

CHEN, TB ;

KLING, PJ ;

KUNKEL, KA ;

SPRINGER, JP ;

HIRSHFIELD, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2235-2246

[9] Didemnidines A and B, Indole Spermidine Alkaloids from the New Zealand Ascidian Didemnum sp. [J].

Finlayson, Rhys ;

Pearce, A. Norrie ;

Page, Michael J. ;

Kaiser, Marcel ;

Bourguet-Kondracki, Marie-Lise ;

Harper, Jacquie L. ;

Webb, Victoria L. ;

Copp, Brent R. .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (04) :888-892

[10] Efficient synthesis of 4-hydroxycyclopentenones: dysprosium(III) triflate catalyzed Piancatelli rearrangements [J].

Fisher, David ;

Palmer, Leoni I. ;

Cook, Jonathan E. ;

Davis, Jessica E. ;

de Alaniz, Javier Read .

TETRAHEDRON, 2014, 70 (27-28) :4105-4110

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