Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones

被引：60

作者：

Balkrishna, Shah Jaimin ^{[1
]}

Bhakuni, Bhagat Singh ^{[1
]}

Kumar, Sangit ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2011年 / 67卷 / 49期

关键词：

ANTIOXIDANT ACTIVITY; CONVENIENT SYNTHESIS; S-S; DRUG EBSELEN; ARYL IODIDE; ORGANOSELENIUM; CLEAVAGE; CHEMISTRY; DICHALCOGENIDES; CYCLIZATION;

D O I：

10.1016/j.tet.2011.09.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Scope of the copper catalyzed/mediated selenium-nitrogen coupling reaction has been studied for the synthesis of isoselenazolones. It is noticed that the 2-chloro, 2-bromo-, and 2-iodo-aryl amides substrates can be exploited in the selenium-nitrogen coupling reaction by employing 25-100 mol % of CuI/1,10-phenanthroline (L) and potassium carbonate as a base in DMF. Furthermore, electron rich 2-chloro-arylamides also underwent selenium-nitrogen coupling reaction to give biologically important selenium-nitrogen heterocycles. Also, copper-catalyzed selenium-nitrogen coupling reaction has been meticulously applied for the synthesis of diaryl diselenides having methoxy, amine, and amide functionality from respective aryl iodides in the presence of stoichiometric amount of succinimide as an external Se-N coupling partner. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：9565 / 9575

页数：11

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