Synthesis of azoles from 3-(3-hydrazino-3-oxopropyl)anilino-and 3-(3-hydrazino-3-oxopropyl)-4-methylanilinopropane hydrazides

摘要

Condensation of 3-(3-hydrazino-3-oxopropyl)anilino-and 3-(3-hydrazino-3-oxopropyl)-4-methylanilinopropane hydrazides with 2,4-pentanedione, phenyl isocyanate or phenyl isothiocyanate (with subsequent work up of the semicarbazides obtained by base), and carbon disulfide gave respectively: 1-(3,5-dimethyl-1H-1-pyrazolyl)-3-3-(3,5-dimethyl-1H-1-pyrazolyl)-3-oxopropylanilino-1-propanone, 3-(2-{2-(5-oxo-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethylanilino}ethyl)-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-5-one and its thio analog, and 5-(2-{2-(2-thioxo-2,3-dihydro-1,3,4-oxadiazol-5-yl)ethylanilino}ethyl)-2,3-dihydro-1,3,4-oxadiazole-2(3H)-thione plus their methyl derivatives.