Highly efficient synthesis and antioxidant capacity of N-substituted benzisoselenazol-3(2H)-ones

Abstract

A new, general one step synthesis of N-substituted benzisoselenazol-3(2H)-ones based on the reaction of o-iodobenzamides with lithium diselenide, is described. A series of alkyl and aryl derivatives was obtained in high yields (up to 98%). Their GPx-like antioxidant activity, tested by NMR, showed a significantly higher activity than ebselen.Scheme 1 Synthetic approaches to benzisoselenazol-3(2H)-one 1.

Water-dependent synthesis of biologically active diaryl diselenides

“…Lithium diselenide is obtained by a modified protocol from selenium and lithium hydroxide in the presence of hydrazine hydrate, and no catalyst is needed for the reaction to proceed. 42 Formation of monoselenides in the reaction mixture was not observed. 37 Addition of water (5%) to the reaction medium enables to obtain diaryl diselenides as the only products directly from o-iodobenzamides (Scheme 4).…”

“…According to our previously proposed mechanism for the formation of ebselen derivatives, in the first reaction step corresponding diselenides are formed, which are then oxidized to benzisoselenazolones. 42 Apparently, the addition of a small amount of water (5%) decreases the solubility of diselenides what prevents further oxidation reactions. Increasing the amount of added water completely inhibited the product formation and the unreacted substrate was isolated after 24 h. Although the newly presented procedure is based on the known reaction of o-iodobenzamides with LiSeSeLi (method i) significant improvements have been achieved.…”

“…First, a series of benzisoselenazolones 1, 9-14 was prepared by two procedures, from 2,2-diselenobis(benzoic acid) (method A) 39 and by our method B, [42][43][44] involving the treatment of N-substituted o-iodobenzamide with dilithium diselenide, providing significantly better yields (Scheme 3).…”

New and efficient methodology for the synthesis of chiral mono- and ditellurides

“…9 Previously, we mainly focused on developing effective methods for the synthesis of new optically active monoterpene derivatives containing sulfur 10 and selenium. [11][12][13][14][15][16][17][18][19] The results prompted us to synthesize analogous structures with tellurium. Among all of the known methodologies to synthesize symmetrical tellurides and ditellurides, the most broadly used is the alkylation or arylation of nucleophilic telluride or ditelluride dianions (a and b).…”

Reactivity of dipinanyl diselenides functionalized at C-10-position with -CH2O(Se)Ph, -OH and -OCPh3 substituents

“…[3][4][5][6][7][8] Looking for new selenium derivatives is also interesting due to their biological and pharmacological functions. [9][10][11][12][13][14][15] Addition to double bonds is one of the most common chemical transformations. Formation of the addition products by organoselenium electrophiles 1 proceeds by a two-step mechanism.…”