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

Supsana, P./ Tsoungas, P. G./ Aubry, A./ Skoulika, S./ Varvounis, G.

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-one oxime furnished 2-ethylbenzo[cd]indol-3(1H)-one 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. (C) 2001 Elsevier Science Ltd. All rights reserved.
Institution and School/Department of submitter: Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
Keywords: naphthalenes,oximes,oxidation,n-oxides,spiro compounds,furoxans
URI: http://olympias.lib.uoi.gr/jspui/handle/123456789/8727
ISSN: 0040-4020
Link: <Go to ISI>://000168146000028
Publisher: Elsevier
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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