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Synthesis 2008(5): 711-718  
DOI: 10.1055/s-2008-1032178
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Synthesis of Naphthopyranoisoxazoles and Versatile Access to ­Naphthopyranoisoxazolines

Theodoros Liaskopoulosa, Stavroula Skoulikaa, Petros G. Tsoungasb, George Varvounis*a
a Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
Fax: +30(26510)98799; e-Mail: gvarvoun@cc.uoi.gr;
b Ministry of Development, Department of Research and Technology, Messogeion Ave. 14-18, 11510 Athens, Greece
Further Information

Publication History

Received 20 November 2007
Publication Date:
18 February 2008 (online)

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Abstract

2-(Alkenyloxy)naphthalene-1-carbaldehyde oximes are oxidized with potassium iodide, iodine and sodium bicarbonate directly to novel naphthopyranoisoxazoles. Naphthopyranoisoxazoles are also prepared from 2-(3-chloroallyloxy)naphthalene-1-carbaldehyde oxime or 2-(alkynyloxy)naphthalene-1-carbaldehyde oximes by oxidation with sodium hypochlorite and triethylamine. The oxidation of 2-(alkenyloxy)naphthalene-1-carbaldehyde oximes with sodium hypochlorite and triethylamine afforded novel naphthopyranoisoxazolines. The former reaction is tentatively proposed to occur via activation of the alkene side chain by means of an iodonium intermediate and either 1,3-dipolar interaction with a nitrile oxide side-group or cyclization with a hydroximic acid iodide side-group.

Key words

cycloadditions - halogenation - heterocycles - oxidations - ring closure

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