1954 年 74 巻 9 号 p. 951-953
By heating isonicotinylhydrazine (I) with carbon disulfide in pyridine, 5-γ-pyridyl-Δ4-1, 3, 4-oxadiazoline-2-thione (III) and 4-isonicotinylamino-3-γ-pyridyl-Δ2-1, 2, 4-triazoline-5-thione (V) were obtained. (III) was also obtained on heating (II) (R=K or R=CH3) in decalin. Treatment of (II) (R=CH3) with conc. sulfuric acid gave 2-methyl-thio-5-γ-pyridyl-1, 3, 4-thiadiazole (VI) which was derived to the methylsulfonyl compound (VII) by oxidation. Application of hydrazine hydrate to (II) (R=CH3) gave 4-amino-3-γ-pyridyl-Δ2-1, 2, 4-triazoline-5-thione (IX) whose desulfuration yielded 4-amino-3-γ-pyridyl-1 H-1, 2, 4-triazole. Methylation of (III) to (XIII) and its oxidation chiefly gave 5-γ-pyridyl-Δ4-1, 3, 4-oxadiazoline-2-one (XII).