An efficient copper mediated synthetic methodology for benzo[d]isothiazol-3(2H)-ones and related sulfur-nitrogen heterocycles

被引：49

作者：

Bhakuni, Bhagat Singh ^{[1
]}

Balkrishna, Shah Jaimin ^{[1
]}

Kumar, Amit ^{[1
]}

Kumar, Sangit ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal IISER, Dept Chem, Bhopal 462023, MP, India

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 11期

关键词：

Copper catalysis; Benzo[d]isothiazol-3(2H)-ones; Carbon-sulfur bond formation; Sulfur; PHOSPHATASE 1B PTP1B; BOND FORMATION; S-S; REDOX REGULATION; ARYL IODIDE; TE BOND; C-S; INHIBITORS; CLEAVAGE; 1,2-BENZISOTHIAZOLIN-3-ONES;

D O I：

10.1016/j.tetlet.2012.01.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper mediated sulfur-nitrogen coupling reaction for the synthesis of benzo[d]isothiazol-3(2H)-ones and related sulfur-nitrogen heterocycles has been presented, which requires 2-halo-arylamides, sulfur powder, 25-50 mol % of copper iodide/1,10-phenanthroline, and potassium carbonate as base. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1354 / 1357

页数：4

共 53 条

[1] CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids [J].

Alves, Diego ;

Santos, Cayane G. ;

Paixao, Marcio W. ;

Soares, Letiere C. ;

de Souza, Diego ;

Rodrigues, Oscar E. D. ;

Braga, Antonio L. .

TETRAHEDRON LETTERS, 2009, 50 (48) :6635-6638

[2] INHIBITORS OF BLOOD-PLATELET AGGREGATION - EFFECTS OF SOME 1,2-BENZISOTHIAZOL-3-ONES ON PLATELET RESPONSIVENESS TO ADENOSINE-DIPHOSPHATE AND COLLAGEN [J].

BAGGALEY, KH ;

ENGLISH, PD ;

JENNINGS, LJA ;

MORGAN, B ;

NUNN, B ;

TYRRELL, AWR .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (11) :1661-1667

[3] Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones [J].

Balkrishna, Shah Jaimin ;

Bhakuni, Bhagat Singh ;

Kumar, Sangit .

TETRAHEDRON, 2011, 67 (49) :9565-9575

[4] Cu-Catalyzed Efficient Synthetic Methodology for Ebselen and Related Se-N Heterocycles [J].

Balkrishna, Shah Jaimin ;

Bhakuni, Bhagat Singh ;

Chopra, Deepak ;

Kumar, Sangit .

ORGANIC LETTERS, 2010, 12 (23) :5394-5397

[5] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[6] Exploring the Structural Requirements for Inhibition of the Ubiquitin E3 Ligase Breast Cancer Associated Protein 2 (BCA2) as a Treatment for Breast Cancer [J].

Brahemi, Ghali ;

Kona, Fathima R. ;

Fiasella, Annalisa ;

Buac, Daniela ;

Soukupova, Jitka ;

Brancale, Andrea ;

Burger, Angelika M. ;

Westwell, Andrew D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (07) :2757-2765

[7] Simple and efficient recyclable catalytic system for performing copper-catalysed S-arylation reactions in the presence of water [J].

Carril, Monica ;

SanMartin, Raul ;

Dominguez, Esther ;

Tellitu, Imanol .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) :5100-5105

[8] Novel alternative for the N-S bond formation and its application to the synthesis of benzisothiazol-3-ones [J].

Correa, Arkaitz ;

Tellitu, Imanol ;

Dominguez, Esther ;

SanMartin, Raul .

ORGANIC LETTERS, 2006, 8 (21) :4811-4813

[9] Potent, Selective, and Orally Available Benzoisothiazolone Phosphomannose Isomerase Inhibitors as Probes for Congenital Disorder of Glycosylation la [J].

Dahl, Russell ;

Bravo, Yalda ;

Sharma, Vandana ;

Ichikawa, Mie ;

Dhanya, Raveendra-Panickar ;

Hedrick, Michael ;

Brown, Brock ;

Rascon, Justin ;

Vicchiarelli, Michael ;

Mangravita-Novo, Arianna ;

Yang, Li ;

Stonich, Derek ;

Su, Ying ;

Smith, Layton H. ;

Sergienko, Eduard ;

Freeze, Hudson H. ;

Cosford, Nicholas D. P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (10) :3661-3668

[10] EXPEDIENT SYNTHESIS OF EBSELEN AND RELATED-COMPOUNDS [J].

ENGMAN, L ;

HALLBERG, A .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2964-2966

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