THE PREPARATION OF SOME THIOSEMICARBAZONES CONTAINING THE s -TRIAZINE RING

Abstract

The reaction between cyanuric chloride and aliphatic thiosemicarbazones results in the formation of 1:1 adducts containing a dichloro-s-triazine ring. Chemical evidence, infrared spectroscopy, and microbiological studies indicate that the addition of the triazine ring takes place at the N 2 atom of thiosemicarbazones. Since cyanuric chloride failed to react similarly with aromatic thiosemicarbazones, a different type of condensation product was obtained by another method, in which cyanuric chloride was first condensed with o-, or p-hydroxybenzaldehyde to give 1:3 adducts containing free carbonyl groups. Reaction of these compounds with thiosemicarbazide gave the corresponding tri-thiosemicarbazones.