Sulfur-containing Pyridine Derivatives. XXIX

Syntheses of Sulfazopyridines

Abstract

[2, 6-Diaminopyridine]-(3-azo-1′)-{4-[4′′-methylthiazolyl-(2′′)]-aminosulfonyl-benzene} (I) is converted into [2-amino-6-hydroxypyridine]-(3-azo-1′)-{4′-[4′′-methylthiazolyl-(2′′)]-aminosulfonylbenzene} (II), yellowish-red microcrystals, m.p. 249-250°, by boiling with dil. HCl. By coupling 2, 6-diaminopyridine, respectively with sulfanilguanidine, 2-[p-aminobenzene]-sulfamido-5-methyl-1, 3, 4-thiodiazole and 2-[p-aminobenzene]-sulfonamido-4-methyl-6-hydroxypyridine, [2, 6-diaminopyridine]-(3-azo-1′)-[4′-guanyl-aminosulfonylbenzene] (III), yellowish-red microcrystals, m.p. 226-8°, [2, 6-diaminopyridine]-(3-azo-1′)-{4′-[5′′-methyl-1′′, 3′′, 4′′-thiodiazolyl-(2′′)]-aminosulfonylbenzene} (IV), yellowish-red microcrystals, m.p. 220-1° (decomp.), and [2, 6-diaminopyridine]-(3-azol-1′)-{4′-[4′′-methyl-6′′-hydroxypyrimidyl-(2′′)]-aminosulfonylbenzene} (V), yellowish-red microcrystals, decompn. 260-2°, are obtained, respectively. When boiled with dil. HCl, the azo-compounds (III) and (VI) gave [2-amino-6-hydroxypyridine]-(3′-azo-1′)-[4′-carbaminyl-aminosulfonylbenzene] (VI), light orange microcrystals, m.p. 156-8°, and [2-amino-6-hydroxypyridine]-(3-azo-1′)-{4′-[5′′-methyl-1′′, 3′′, 4′′-thiodiazolyl-(2′′)]-aminosulfonylbenzene} (VII), yellowish-red microcrystals, m.p. 256-7° (decomp.), respectively.