THE PREPARATION OF SOME THIOSEMICARBAZONES CONTAINING THE s-TRIAZINE RING

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 N2 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.