SYNTHESIS an‎d CHARACTERIZATION OF NEW 1-NAPHTHYL-3, 5-DISUBSTITUTED TRIAZOLES

Novel oxazolin-5-one derivatives 1a,b were prepared and used as starting materials for the synthesis of triazolobenzimidazole derivatives 2a,b, N-4`-aminophenyl-1-naphthyl 5-substituted 1,2,4-triazol-3- carboxyamide 3a,b. The reaction of compounds 1a,b with resorcinol, 1- and/or 2-naphthols gave triazolo- 3-carboxylate derivatives 4a-f. Compounds 4a,b,d,e were rearranged according to the Fries rearrangement reaction to give 5a-d. Fries rearrangement products 8a,b have been obtained also by refluxing compounds 3a,b with anhydrous zinc chloride and acetic acid. Reaction of Fries rearrangement products 5a-d and/or 8a,b with malononitrile in acetic acid, dry benzene and ammonium acetate gave compounds 6a,b , 7a,b and/or 9a,b respectively.