Author:

Keywords:

Cerium(IV) ammonium nitrate, benzoylhydrazones, nitration, oxidative rearrangement, electrocyclisation, benzo[f]phthalazines, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, ONE-POT SYNTHESIS, PHENOLIC HYDROXYL, ORGANIC-SYNTHESIS, DRUG DISCOVERY, FACILE ROUTE, HYDRAZONES, CHEMISTRY, 2-ARYLBENZOTHIAZOLES, 1,2-DIACYLBENZENES, ACYLHYDRAZONES, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

A novel nitration and oxidation reaction sequence of 2-Acetyl-1-naphthol benzoylhydrazones with CAN is presented. There is strong indication that nitration precedes an oxidative rearrangement to 1,2-diacyl-4- nitronaphthalenes or oxidative electrocyclisation to 3-methyl-5-nitronaphtho[2,1-d]isoxazole. Condensation of 1,2-diacyl-4-nitronaphthalenes with hydrazine hydrate yields 1,4-disubstituted benzo[f]phthalazines.