Tetrahedron

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

…, PG Tsoungas, A Aubry, S Skoulika, G Varvounis

Index: Supsana, Paraskevi; Tsoungas, Petros G; Aubry, Andre; Skoulika, Stavroula; Varvounis, George Tetrahedron, 2001 , vol. 57, # 16 p. 3445 - 3453

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Citation Number: 22

Abstract

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-hydroxy-1-naphthyl) propan-1- ...