Ru-catalyzed oxidation and C-C bond formation of indoles for the synthesis of 2-indolyl indolin-3-ones under mild reaction conditions

被引：8

作者：

Zhou, Xiao-Yu ^{[1
]}

Chen, Xia ^{[1
]}

机构：

[1] Liupanshui Normal Univ, Sch Chem & Mat Engn, Liupanshui 553004, Peoples R China

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2020年 / 98卷 / 11期

关键词：

ruthenium; oxidation; indoles; indolin-3-one; TBHP; N-BOC INDOLES; DEAROMATIZATION; MITOMYCIN; ISATINS;

D O I：

10.1139/cjc-2019-0288

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we described a ruthenium catalyzed oxidation and C-C bond formation reaction of 2-alkyl or 2-aryl substituted indoles using tert-butyl hydroperoxide (TBHP) as oxidant. Coupled with cascade transformation, it provided a mild catalytic oxidation system for the synthesis of 2-indolylindolin-3-ones. The reaction could readily occur using RuCl3 center dot 3H(2)O as catalyst, and the target product was obtained with medium to high yield.

引用

页码：667 / 669

页数：3

共 25 条

[1] I2/TBHP-Catalyzed Chemoselective Amination of Indoles [J].

Cai, Zhong-Jian ;

Wang, Shun-Yi ;

Ji, Shun-Jun .

ORGANIC LETTERS, 2013, 15 (20) :5226-5229

[2] Synthesis of the mitomycin and FR900482 ring systems via dimethyldioxirane oxidation [J].

Colandrea, VJ ;

Rajaraman, S ;

Jimenez, LS .

ORGANIC LETTERS, 2003, 5 (06) :785-787

[3] Oxidation of indoles and 1,2-dihydro-3H-indol-3-ones [J].

Desarbre, E ;

Savelon, L ;

Cornec, O ;

Merour, JY .

TETRAHEDRON, 1996, 52 (08) :2983-2994

[4] Substituent-Directed Regioselective Azidation: Copper-Catalyzed C-H Azidation and Iodine-Catalyzed Dearomatizative Azidation of Indole [J].

Dhineshkumar, Jayaraman ;

Gadde, Karthik ;

Prabhu, Kandikere Ramaiah .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) :228-235

[5] ON THE SYNTHESIS AND EXTRAORDINARY CONFIGURATIONAL STABILITY OF THE C-9A-HYDROXYLATED MITOMYCINS IN THE 10-DECARBAMOYLOXY-9-DEHYDRO SERIES - FULLY SYNTHETIC ROUTES TO NOVEL MITOMYCIN CONGENERS [J].

FEIGELSON, GB ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3391-3393

[6] Stereoselective synthesis of oxazino[4,3-a] indoles employing the oxa-Pictet-Spengler reaction of indoles bearing N-tethered vinylogous carbonate [J].

Gharpure, Santosh J. ;

Sathiyanarayanan, A. M. .

CHEMICAL COMMUNICATIONS, 2011, 47 (12) :3625-3627

[7] Oxidative Dearomatization of Indoles via Pd-Catalyzed C-H Oxygenation: An Entry to C2-Quaternary Indolin-3-ones [J].

Guchhait, Sankar K. ;

Chaudhary, Vikas ;

Rana, Vijay A. ;

Priyadarshani, Garima ;

Kandekar, Somnath ;

Kashyap, Maneesh .

ORGANIC LETTERS, 2016, 18 (07) :1534-1537

[8] Total Synthesis of (+)-Isatisine A [J].

Karadeolian, Avedis ;

Kerr, Michael A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (06) :1133-1135

[9] Enantioselective total synthesis of (-)-flustramines A, B and (-)-flustramides A, B via domino olefination/isomerization/Claisen rearrangement sequence [J].

Kawasaki, T ;

Shinada, M ;

Kamimura, D ;

Ohzono, M ;

Ogawa, A .

CHEMICAL COMMUNICATIONS, 2006, (04) :420-422

[10] First total synthesis of dragmacidin A via indolylglycines [J].

Kawasaki, T ;

Enoki, H ;

Matsumura, K ;

Ohyama, M ;

Inagawa, M ;

Sakamoto, M .

ORGANIC LETTERS, 2000, 2 (19) :3027-3029

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