M. M. Aly

THERMOLYSIS AND PHOTOLYSIS OF SOME THIOUREA DERIVATIVES (PART I)

Abstract Thermolysis of N-benzoyl-N′-phenylthiourea (BPTU) on heating in air at 230°C gives NH3, H2S, benzaldehyde, benzil, aniline, azobenzene, benzamide, benzanilide, phenylisothiocyanate, phenyl-cyanamide, thiocarbanilide and benzoylisothiocyanate, whereas thermolysis of N-benzoy1-N′-benzylthiourea (BBTU) affords NH3, H2S, benzaldehyde, benzil, toluene, bibenzyl, stilbene, benzamide, cyanamide, benzylisothiocyanate, benzoylthiourea and benzoylisothiocyanate. Thermolysis of N-benzoyl-N′-α-naphthylthiourea (BNTU) under the same conditions gives NH3, H2S. benzaldehyde, benzil, benzamide, α-naphthylisothiocyanate, α-naphthanilide, α-naphthylcyanamide. benzoylisothiocyanate, α-naphthylamine and N,N′-di-α,α′-naphthylthiourea. Analogous results were also obtained on photolysis of (BFTU), (BBTU) and (BNTU) with the exception of NH3, and the photodegradation products of phenylthiourea, benzylthiourea and a-naphthylthiourea respectively. The main feature of these pyrolyses is the homolysis of the amide and thioa...

THERMOLYSIS AND PHOTOLYSIS OF ARYL THIOCARBAMATE DERIVATIVES

Abstract Thermolysis of N-phenyl-O-phenylthiocarbamate (POPTC), N-phenyl-O-benzylthiocarbamate (POBTC), and N-phenyl-S-phenylthiocarbamate (PSPTC) by reflux for 15 hr at 220–230 °C affords degradation products assumed to be formed by homolysis at different sites furnishing free radicals that undergo subsequent reactions involving H-abstraction, dimerization, disproportionation and/or fragmentation to give the identitied products. Similar results are also obtained on photolysis of such thiocarbamate derivatives.

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.