Issue 21, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
07 Ker. 2018
Accepted
25 Gen. 2019
First published
28 Gen. 2019

Dalton Trans., 2019,48, 7249-7260

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, 48, 7249 DOI: 10.1039/C8DT04832K

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