ORGANIC SELENIUM COMPOUNDS. PART II. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME NEW SYMMETRICAL DIARYLSELENIDES CONTAINING THIAZOLYL, THIAZOLIDIN-4-ONYL, AZETIDIN-2-ONYL, TRIAZOLIN-1-YL AND GLYCYL MOIETIES

摘要

4,4-Dimonochloroacetyl diphenylselenide (2) was prepared as a new precursor for the title studies by chloroacetylation of diphenylselenide (1). 2 interacts with thiourea to afford 4,4-di(2-aminothiazol-4-yl)diphenylselenide (3). Condensation of 3 with aromatic aldehydes in the presence of a catalytic amount of dry piperidine furnished aldimines (4). Interaction of 4 with mercaptoacetic acid afforded 4,4-di(2-(2'"-substituted phenyl-3'"-thiazolo-4'"-thiazolidinon)-3'"-yl)diphenylselenides (6). Schiff bases 4 interact with mono chloroacetyl chloride in dry dioxane and triethylamine produced 4,4-di(2-(4'"-substituted phenyl-3'"-chloro-2'"-azetidinon-1'"-thiazolo)-1'"-yl)diphenylselenides (8). 1,3-Dipolar cyclonucleophilic addition of diazomethane to certain of 4 gave 4,4-di(2-(5'"-substituted phenyl-(2)-1'",2'",3'"-triazoline thiazolo)-1'"-yl)diphenylselenides (10). 2 interacts with secondary heteroalicyclic amines to afford 4,4-diglycyl diphenylselenides (11). The structures of the synthesized compounds are based on correct physical data, IR, H-1 NMR, C-13 NMR, and by chemical means. Some of the synthesized compounds were biologically tested.