[Selenazoles. XII. (1) Reaction of 4-(p-tolyl)-selenosemi-carbazides of acetic, benzoic, isonicotinic, nicotinic and picolinic acid with omega-acetophenone].
The cyclization of 4-(p-tolyl)-selenosemicarbazides of acetic, benzoic, isonicotinic, nicotinic and picolinic acids (Ia-e) with omega-bromoacetophenone was investigated in the medium of methanol (Method A) or in methanol in the presence of anhydrous sodium acetate (Method B). Acid hydrolysis of compounds IIf-i and IVa-c, e was studied. Results of UV and IR spectrometric measurements and of the in vitro microbiological studies are presented. In contradistinction to corresponding thiosemicarbazides, the change in N4 nitrogen atom basicity of the parent selenosemicarbazide I (pKa of p-toluidine = 5.1), in comparison to that of 4-phenyl-selenosemicarbazide (pKa of aniline = 4.63), proved to influence the equilibrium of the reaction with omega-bromoacetophenone only in the methanol medium without addition of anhydrous sodium acetate (Method A).
Biliński
S
S
Bielak
L
L
Chmielewski
J
J
Marcewicz-Rojewska
B
B
Musik
I
I
D000085:Acetates; D019342:Acetic Acid; D000098:Acetophenones / Q000138:chemical synthesis / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001565:Benzoates; D019817:Benzoic Acid; D055598:Chemical Phenomena; D002621:Chemistry; D003500:Cyclization; D004352:Drug Resistance, Microbial; D004755:Enterobacteriaceae / Q000187:drug effects; D066298:In Vitro Techniques; D007539:Isonicotinic Acids; D009525:Niacin; D010848:Picolinic Acids; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012643:Selenium / Q000494:pharmacology*; D012663:Semicarbazides / Q000138:chemical synthesis / Q000494:pharmacology*; D013210:Staphylococcus / Q000187:drug effects; D013291:Streptococcus / Q000187:drug effects; D014050:Toluene / Q000138:chemical synthesis / Q000494:pharmacology*
D000085:Acetates; D000098:Acetophenones; D000900:Anti-Bacterial Agents; D001565:Benzoates; D007539:Isonicotinic Acids; D010848:Picolinic Acids; D012663:Semicarbazides; D009525:Niacin; C010059:carbamylhydrazine; D014050:Toluene; C013190:phenacyl bromide; D019817:Benzoic Acid; D012643:Selenium; D019342:Acetic Acid; C030614:picolinic acid
Selenazole. XII. (1) Reakcje 4-(p-tolilo)-selenosemikarbazydow kwasu octowego, benzoesowego, izonikotynowego, nikotynowego i pikolinowego z omega-bromoacetofenonem.