1962 年 82 巻 2 号 p. 233-238
[Correction] Journal of the Pharmaceutical Society of Nippon Vol.83 No.6 (1963) pp.e1b-e1b
[Correction] Journal of the Pharmaceutical Society of Nippon Vol.82 No.8 (1962) pp.e3ae-e3ae3-Chloro-4-methyl-6-sulfanilamidopyridazine(VI-B), 3-chloro-4, 5-dimethyl-6-sulfanil-amidopyridazine(VI-C), and 3-chloro-4, 5-tetramethylene-6-sulfanilamidopyridazine(VI-E) were prepared by hydrolysis of N4-acetylated compound of (VI), obtained by condensation of the corresponding 3-chloro-6-amino derivatives (V) with p-acetamidoben-zenesulfonyl chloride in pyridine. 1-Chloro-4-sulfanilamidophthalazine (VI-D) was prepared by fusion of 1, 4-dichlorophthalazine (IV-D) with potassium salt of sulfanilamide. Heating of (VI-B) and (VI-D) with sodium alkoxide afforded the corresponding alkoxyl derivatives (VIII). Catalytic reduction of (VI-B) and (VI-C) respectively gave 4-methyl-6-sulfanilamidopyridazine (VII-B) and 4, 5-dimethyl-6-sulfanilamidopyridazine (VII-C). 3, 6-Dichloro-4, 5-tetramethylenepyridazine (IV-E) failed to undergo amination on heating with aqueous ammonia but afforded 3-chloro-6-amino derivative (V-E) on being heated with alcoholic ammonia. 4, 5-Tetramethylene-6-methyl-3-pyridazinol (XVIII) was obtained by heating 3, 4, 5, 6-tetrahydrophthalic anhydride and malonic acid in pyridine and addition of hydrazine hydrate to ethanolic solution of its product.
