SYNTHESIS OF DIARYLSULPHIDES AND DIARYLSULPHONES CONTAINING PYRAZOLINE, ISOXAZOLINE, PYRIMIDINE AND CONDENSED PYRIDAZINE MOIETIES

Abstract

Arylhydrazones 2a-c obtained by the reaction of diazotized 4-amino-4′-nitrodiaryi sulphide (1) with active methylene compounds i.e. ethyl acetoacetate, acetylacetone and diethyl malonate are condensed with hydrazines, hydroxylamine, urea and thiourea to give the corresponding pyrazolines (3, 4, 8, 9, 13), isoxazolines (5, 10) and pyrimidines (6, 7, 11, 12, 14, 15). Intramolecular cyclization of arylhydrazones 2a, c with AlCl₃ in chlorobenzene yielded the cinnoline derivatives (16, 17). Reaction of cinnoline derivative (16) with hydrazines afforded the corresponding pyrazolo[4,3-c]cinnoline derivatives (18, 19). Oxidation of some of the prepared sulphides with H₂O₂/AcOH at room temperature gave the corresponding sulphones (20-30).

Key Words:

• Synthesis
• Diarylsulphides
• Diarylsulphones
• Pyrazoline
• Pyrimidine
• cinnoline.