Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones

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...

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Bibliographic Details
Published in:Tetrahedron 2011-12, Vol.67 (49), p.9565-9575
Main Authors: Balkrishna, Shah Jaimin, Bhakuni, Bhagat Singh, Kumar, Sangit
Format: Article
Language:English
Subjects:
Amides
Chemical reactions
Chemistry
Copper
Exact sciences and technology
FABRICATION
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Iodides
JOINING
Organic chemistry
Preparations and properties
Succinimides
Synthesis (chemistry)
Tetrahedrons
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.09.141