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

GRAPHICAL ABSTRACT

Abstract

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-Δ²-1‴,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, ¹H NMR, ¹³C NMR, and by chemical means. Some of the synthesized compounds were biologically tested.

Keywords:

• Diarylselenides
• thiazoles
• thiazolidinones
• azetidinones
• biological testing