Oxidation of 1-acyl-2-naphthol oximes:peri-and o-cyclisation and spiro cyclodimerisation of naphthoquinone nitrosomethide intermediates

摘要

The oxidation of 2-hydroxynaphthaldehyde oxime with lead(IV) acetate (LTA) gave a mixture of naphtho[1,8-de][1,2]oxazine and a spiro dimer.LTA oxidation of 6-bromo (or nitro)-2-hydroxynaphthaldehyde oximes provided only spiro dimers.Similar treatment of (2-hydroxy-1-naphthyl)keto oximes with LTA gave naphtho[1,8-de][1,2]oxazines and benzo[cd]indol-3(1H)-ones.Low temperature oxidation of 1-(2-hydroxyl-1-naphthyl)propan-1-one oxime furnished 2-ethylbenzo[cd]indol-3(1H)-oee and 1-ethylnaphtho[1,2-d]isoxazole-2-oxide.peri- and o-Naphthoquinone nitrosomethides are invoked as intermediates that undergo peri- and o-cyclisation and intermolecular cyclodimerisation.