[Synthesis and properties of 5(4,6-diphenyl-2-pyrimidin-2-yl)-1,2,4-triazolin-3-thione and derivatives ].
By treatment of 4,6-diphenyl-pyrimidin-2-carboxyl chloride (1) with thiosemicarbazide the acylthiosemicarbazide 3 has been synthesized. Compound 3 could also be obtained by action of hydrazide on potassium thiocyanate. 5-(4,6-Diphenyl-pyrimidin-2-yl)-1,2,4-triazolin-3-thione (5) could be prepared either by basecatalyzed cyclization of acylthiosemicarbazide or by the reaction of methyl 4,6-diphenyl-pyrimidin-2-carboxylate with thiosemicarbazide in the presence of sodium methoxide. Alkylation of the 1,2,4-triazolin-3-thione 5 with chloroacetic acid resulted in formation of the S-carboxymethyl derivative 6. On heating, with a mixture of glacial acetic acid/acetic anhydride, compound 6 afforded 6-(4,6-diphenyl-pyrimidin-2-yl)thiazolo[3,2-b]-1,2,4-triazol-3(2H) -one (7). Condensation of 7 with aromatic aldehydes yielded 2-arylidene-6-(4,6-diphenyl-pyrimidin-2-yl)thiazolo[3,2-b]-1,2,4-+ ++triazol-3(2H)-ones, which could also be prepared by treatment of the S-carboxymethyl derivative 6 with an appropriate aldehyde in the presence of acetic acid and acetic anhydride. Some of the synthesized compounds possess a weak antiinflammatory activity.
Mekuskiene
G
G
Institut für Materialforschung und angewandte Wissenschaften, Universität Vilnius, Litauen.
Gaidelis
P
P
Vainilavicius
P
P
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D002351:Carrageenan; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
C111730:5-(4,6-diphenylpyrimidin-2-yl)-1,2,4-triazolin-3-thione; D000894:Anti-Inflammatory Agents, Non-Steroidal; D011743:Pyrimidines; D014230:Triazoles; D002351:Carrageenan
Synthese und Eigenschaften von 5-(4,6-Diphenyl-pyrimidin-2-yl)-1,2,4-triazolin-3-thion und seinen Derivaten.