Au-Catalyzed Synthesis of Thiopyrano[2,3-b]indoles Featuring Tandem Rearrangement and Hydroarylation

被引：28

作者：

Jha, Mukund ^{[1
]}

Dhiman, Shiv ^{[1
,2
]}

Cameron, T. Stanley ^{[3
]}

Kumar, Dalip ^{[2
]}

Kumar, Anil ^{[2
]}

机构：

[1] Nipissing Univ, Dept Biol & Chem, North Bay, ON P1B 8L7, Canada

[2] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India

[3] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4J3, Canada

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 08期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

ANNULATED SULFUR HETEROCYCLES; DIELS-ALDER REACTION; VILSMEIER FORMYLATION; DIVERGENT SYNTHESIS; ORGANIC-SYNTHESIS; FUSED INDOLES; ANALOGS; THIOPYRANO; DERIVATIVES; INDOLINE-2-THIONES;

D O I：

10.1021/acs.orglett.7b00617

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold(III)-catalyzed synthesis of 14-pi electron heteroaromatic thiopyrano[2,3-b]indole is reported using conjugated enyne tethered indole sulfides, featuring skeletal rearrangement conjoined with intramolecular hydroarylation (via C3-H functionalization of the indole core) and oxidative aromatization. Subsequent Pd-catalyzed C-C coupling resulted in a 16-pi electron heteroaromatic isothiochromeno[1,8,7-bcd]indole.

引用

收藏

页码：2038 / 2041

页数：4

相关论文

共 46 条

[1] Cascade radical reactions via α-(arylsulfanyl)imidoyl radicals:: Competitive [4+2] and [4+1] radical annulations of alkynyl isothiocyanates with aryl radicals [J].

Benati, L ;

Calestani, G ;

Leardini, R ;

Minozzi, M ;

Nanni, D ;

Spagnolo, P ;

Strazzari, S ;

Zanardi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3454-3464

[2]

Berlin K. D., 2003, U.S. Patent, Patent No. [6,586,460, 6586460]

[3] Bronsted acid-catalyzed rapid enol-ether formation of 2-hydroxyindole-3-carboxaldehydes [J].

Blanchard, Darian ;

Cameron, T. Stanley ;

Jha, Mukund .

MOLECULAR DIVERSITY, 2013, 17 (04) :827-834

[4]

BOURDAIS J, 1970, TETRAHEDRON LETT, P2895

[5] The antimicrobial natural product chuangxinmycin and some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase [J].

Brown, MJ ;

Carter, PS ;

Fenwick, AE ;

Fosberry, AP ;

Hamprecht, DW ;

Hibbs, MJ ;

Jarvest, RL ;

Mensah, L ;

Milner, PH ;

O'Hanlon, PJ ;

Pope, AJ ;

Richardson, CM ;

West, A ;

Witty, DR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (21) :3171-3174

[6] Poly(ethylene glycol) (PEG) as a reusable solvent medium for organic synthesis. Application in the Heck reaction [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Sultana, SS ;

Reddy, NR .

ORGANIC LETTERS, 2002, 4 (25) :4399-4401

[7] Enantioselective Construction of Functionalized Thiopyrano-lndole Annulated Heterocycles via a Formal Thio [3+31-Cyclization [J].

Chen, Xiang ;

Qi, Zheng-Hang ;

Zhang, Shao-Yun ;

Kong, Ling-Pei ;

Wang, Yong ;

Wang, Xing-Wang .

ORGANIC LETTERS, 2015, 17 (01) :42-45

[8] An expedient synthesis of salviadione [J].

Cummings, Matthew M. ;

Clawson, Ronald W., Jr. ;

Sharma, Sriganesh B. ;

Byerly, Rachel A. ;

Akhmedov, Novruz G. ;

Soederberg, Bjoern C. G. .

TETRAHEDRON, 2011, 67 (26) :4753-4757

[9] Gold Catalysis - Steadily Increasing in Importance [J].

Echavarren, Antonio M. ;

Hashmi, A. Stephen K. ;

Toste, F. Dean .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (09) :1347-1347

[10] Transition-Metal-Catalyzed p-Bond-Assisted C-H Bond Functionalization: An Emerging Trend in Organic Synthesis [J].

Gandeepan, Parthasarathy ;

Cheng, Chien-Hong .

CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (04) :824-838

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