SYNTHESE UND REAKTIONEN VON HYDRAZINO-1,6,6aλ⁴-TRITHIA-3,4-DIAZAPENTALENEN

Abstract

The reaction of 2,5-bis(aroxy)trithiapentalenes 1 with hydrazines and amines to yield different hete-rocycles was studied. 5-Aroxy-2-hydrazino-pentalenes 3 has been found on reaction of 1 with hydrazines 2. At room temperatures unstable, but isolable ammonium salts 4 and at higher temperatures 5-amino-2-hydrazino-thiapentalenes 5 has been isolated from 3 and amines. The reaction of 3 with two equivalent of amines furnished 2,4-diamino-6-hydrazono-1,3,5-thiadiazines 6 under ring transformation reaction. Oxidation of 3 and 5 with lead dioxide gave azo compounds 7. The structure of the prepared compounds was inferred from their ¹H and ¹³C n.m.r. spectra and X-ray analysis of 4c and 6a.

Key Words:

• 1,6,6aλ⁴-Trithia-3,4-diazapentalenes
• 1,3,5-thiadiazines
• X-ray
• ¹H n.m.r.
• ¹³C n.m.r.