2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Pyridine derivatives are also useful as small-molecule 浼?helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Synthetic Route of C12H8N4O
The chemistry of 1,3,4-oxadiazoles with regard to the chemotherapy of tuberculosis was written by Novotny, A.;Brezik, Z.;Pridal, J.;Kalfus, K.. And the article was included in Cesko-Slovenska Farmacie in 1958.Synthetic Route of C12H8N4O This article mentions the following:
2-(4-Pyridyl)-4,5-dihydro-1,3,4-oxadiazol-5-one (I) was prepared by the action of COCl2 on isonicotinic acid hydrazide (II) at 0-5鎺?according to Lieser and Nischk (C.A. 44, 3979h), U.S. 2,665,279 (C.A. 49, 2521g), and Ger. 923,722 (C.A. 51, 12983c), in 90% yield, m. 275.9-6.1鎺?(hot water). Similarly was prepared from NCCH2CONHNH2 (III) and COCl2 88% 2-cyanomethyl-4,5-dihydro-1,3,4-oxadiazol-5-one (IV), m. 162.2-2.3鎺?(EtOH). A new procedure is described for the preparation of N1N2-diacylhydrazines. II (13.7 g.) mixed with 29.1 mL. 80% HCO2H, allowed to stand 8 h. at laboratory temperature, evaporated in vacuo, and the residue crystallized from 235 mL. AcOBu yielded 83% N1-formyl-N2isonicotinoylhydrazine, m. 141.2-1.7鎺? Similarly were prepared: N1-formyl-N2-cyanohydrazine, m. 153.2-3.8鎺?(EtOH); N1-acetyl-N2-isonicotinoylhydrazine (V) from II, water, and AcOAc, m. 162.2-2.5鎺?(AcOBu); N1propionyl-N2-isonicotinoylhydrazine, m. 130.2-0.4鎺?(AcOBu); N1-butyryl-N2-isonicotinoyl-hydrazine, m. 140.1-0.3鎺?(2:1 AcOBu-C5H5N). 2-Alkyl-5-(4-pyridyl)-1,3,4-oxadiazoles were prepared by the modified method of McMillan, et al. (C.A. 48, 11413h). V (5.37 g.) and 5 g. P2O5 heated with stirring to 100-30鎺? the resulting product dissolved after cooling in 100 mL. water and pH simultaneously made to 8-9 with Na2CO3, the solution evaporated, dried, the residue extracted 4 h. with C5H5N in a Soxhlet apparatus, the excess solution evaporated, and crystallized 15 h. at 4鎺?yielded 26% 2-methyl-5-(4-pyridyl)-1,3,4-oxadiazole, m. 150.5-1.0鎺?(boiling EtOH). Similarly was prepared 29% 2-Et derivative m. 58.0-8.5鎺?(EtOH), while the synthesis of the 2-Pr derivative and 2-(4-pyridyl)-1,3,4-oxadiazole was not successful. Dehydration was also achieved by heating with high boiling ethers (Ph2O) to 250-70鎺?and by azeotropic dehydration (25-30% yields). Bacteriol. tests showed a high tuberculostatic effect in vivo of I (similar to II) and IV (similar to III), while 2-alkyl-5-(4-pyridyl)-1,3,4-oxadiazoles showed in vitro only a low activity. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Synthetic Route of C12H8N4O).
2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Pyridine derivatives are also useful as small-molecule 浼?helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Synthetic Route of C12H8N4O
Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem