An efficient iodine pentoxide-triggered iodocarbocyclization for the synthesis of iodooxindoles in water

被引：17

作者：

Zhang, Ming-Zhong ^{[1
]}

Wang, Xin ^{[1
]}

Gong, Ming-Ying ^{[1
]}

Chen, Lin ^{[1
]}

Shi, Wen-Bing ^{[1
]}

He, Shu-Hua ^{[1
]}

Jiang, Yong ^{[1
]}

Chen, Tieqiao ^{[2
]}

机构：

[1] Yangtze Normal Univ, Sch Chem & Chem Engn, Chongqing 408100, Peoples R China

[2] Hainan Univ, Coll Mat & Chem Engn, State Key Lab Marine Resource Utilizat South Chin, Haikou 570100, Hainan, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 28期

关键词：

METAL-FREE SYNTHESIS; MEDIATED ELECTROPHILIC CYCLIZATION; ACTIVATED ALKENES; N-ARYLACRYLAMIDES; SODIUM TRIFLUOROMETHANESULFINATE; SUBSTITUTED QUINOLINES; CONTAINING OXINDOLES; INTRAMOLECULAR ARYLATION; ALKYNES; TRIFLUOROMETHYLATION;

D O I：

10.1039/c8ob01130c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient iodocarbocyclization of alkenes for the synthesis of iodooxindoles has been developed. This reaction proceeds in a chemoselective manner and shows excellent tolerance of various functional groups, including a chemosensitive hydroxymethyl group. Nonmetal inorganic iodine pentoxide was used as both the oxidant and iodine source, making this protocol very practical. On the basis of experimental observations, a plausible electrophilic reaction mechanism was proposed.

引用

页码：5197 / 5202

页数：6

共 63 条

[1] Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes [J].

Aggarwal, Trapti ;

Kumar, Sonu ;

Verma, Akhilesh K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (32) :7639-7653

[2] Intramolecular arylation reactions of alkenes:: A flexible approach to chromans and tetrahydroquinoline derivatives [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3416-3417

[3] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409

[4] Iodocarbocyclization reaction of β-ketoesters and alkynes [J].

Barluenga, Jose ;

Palomas, David ;

Rubio, Eduardo ;

Gonzalez, Jose M. .

ORGANIC LETTERS, 2007, 9 (15) :2823-2826

[5] Direct intramolecular arylation of aldehydes promoted by reaction with IPy2BF4/HBF4:: Synthesis of benzocyclic ketones [J].

Barluenga, Jose ;

Trincado, Monica ;

Rubio, Eduardo ;

Gonzalez, Jose M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3140-3143

[6] A brief synthesis of beta-iodofurans [J].

Bew, SP ;

Knight, DW .

CHEMICAL COMMUNICATIONS, 1996, (09) :1007-1008

[7] Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes [J].

Chen, Zhengwang ;

Huang, Gao ;

Jiang, Huanfeng ;

Huang, Huawen ;

Pan, Xiaoyan .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (04) :1134-1139

[8] Decarboxylative Synthesis of Functionalized Oxindoles via An Iron-Initiated Radical Chain Process and Application in Constructing Diverse Fused-Indoline Heterocycles [J].

Cui, Zhihao ;

Du, Da-Ming .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) :93-99

[9] Computational studies of (HIO3) isomers and the HO2+IOreaction pathways [J].

Drougas, E ;

Kosmas, AM .

JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (17) :3887-3892

[10] Metal-Free Synthesis of 3,3-Disubstituted Oxoindoles by Iodine(III)-Catalyzed Bromocarbocyclizations [J].

Fabry, David C. ;

Stodulski, Maciej ;

Hoerner, Stefanie ;

Gulder, Tanja .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (35) :10834-10838

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