Abstract
Cerium(IV) ammonium nitrate for the tandem nitration and oxidative rearrangement of 2-acetyl-1-naphthol benzoylhydrazones into 1,2-diacylnaphthalenes; synthesis of benzo[f]phthalazines
Highlights
Cerium(IV) ammonium nitrate (CAN) has received considerable attention as a powerful one-electron oxidant with many uses in organic synthesis
CAN has played a significant role in oxidative cyclisations giving access to various heterocycles, the synthesis of five-membered rings with two heteroatoms is limited to benzimidazoles,[3] pyrazoles,[4] benzothiazoles[5,6] and isoxazoles.[7]
A transformation of the latter to 1,2diacylbenzenes was first reported by Kotali and Tsoungas[9,10] using lead tetraacetate (LTA) and its mechanism was studied by Katritzky et al.[11]
Summary
Cerium(IV) ammonium nitrate (CAN) has received considerable attention as a powerful one-electron oxidant with many uses in organic synthesis. Reactions of CAN include, oxidation, oxidative addition, oxidative catalysis, nitration, photo–oxidation, carbon–carbon and carbon–heteroatom bond formation, carbon-carbon, carbon-heteroatom and Si–O bond cleavage, fragmentation, alkoxylation, esterification and transesterification, dehydrogenation, catalysis of multicomponent syntheses and polymer grafting, as described in recent review articles.[1,2] CAN has played a significant role in oxidative cyclisations giving access to various heterocycles, the synthesis of five-membered rings with two heteroatoms is limited to benzimidazoles,[3] pyrazoles,[4] benzothiazoles[5,6] and isoxazoles.[7] CAN has been reported to cleave semicarbazones to the corresponding aldehydes and ketones[8] but hydrazones are not affected. It is worth noting that 2,3-diacylnaphthalenes are known,[21] while their 1,2-diacyl regioisomers are hitherto unreported
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