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An efficient copper-catalyzed synthesis of symmetrical bis(N-arylbenzamide) selenides and their conversion to hypervalent spirodiazaselenuranes and hydroxy congeners

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Abstract

A copper catalyzed efficient synthetic method has been developed to access bis(N-arylbenzamide) selenides from 2-halo-N-arylbenzamide substrates and disodium selenide in HMPA at 110 °C. The developed protocol tolerates substituents in both N-aryl and benzamide rings of the 2-halobenzamide substrates and provides an array of bis(N-arylbenzamide) selenides in practical yields. The resulting selenides were transformed into hypervalent spirodiazaselenuranes by oxidation using aqueous hydrogen peroxide. (N-(1-Naphthyl)) spirodiazaselenurane is also structurally characterized by a single crystal X-ray study. Hydroxy-substituted spiroselenuranes have been prepared by careful demethylation of methoxy-substituted selenides followed by oxidation by hydrogen peroxide. Antioxidant properties for the decomposition of hydrogen peroxide and for the deactivation of radicals of hydroxy-substituted spiroselenuranes have been studied by the thiol assay and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Both hydroxy-substituted spiroselenuranes exhibit dual mimic functions of glutathione peroxidase (GPx) selenoenzyme and α-tocopherol for decomposition of hydrogen peroxide and deactivation of radicals, respectively.

Graphical abstract: An efficient copper-catalyzed synthesis of symmetrical bis(N-arylbenzamide) selenides and their conversion to hypervalent spirodiazaselenuranes and hydroxy congeners

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Publication details

The article was received on 07 Dec 2018, accepted on 25 Jan 2019 and first published on 28 Jan 2019


Article type: Paper
DOI: 10.1039/C8DT04832K
Citation: Dalton Trans., 2019, Advance Article

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    An efficient copper-catalyzed synthesis of symmetrical bis(N-arylbenzamide) selenides and their conversion to hypervalent spirodiazaselenuranes and hydroxy congeners

    R. Kadu, M. Batabyal, H. Kadyan, A. L. Koner and S. Kumar, Dalton Trans., 2019, Advance Article , DOI: 10.1039/C8DT04832K

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