Conversion of bis(o-nitrophenyl)diselenides to heterocycles containing selenium and nitrogen with the aid of samarium diiodide

Treatment of bis (o-nitrophenyl)diselenides with SmI2 led to simultaneous reduction of nitro groups and reductive cleavage of Se-Se bonds as well as to the formation of the intermediates 2. The intermediates 2 were "living" double-anions formed in situ, and reacted readily with omega-bromoketones and alpha-bromocarboxylic acid derivatives to afford the desired 2H-1,4-benzoselenazines and 2H-1,4-benzoselenazin-3(4H)-ones, respectively, in moderate to high yields and under mild conditions. (C) 2002 Wiley Periodicals, Inc.