Novel Synthesis of Naphthopyranoisoxazoles and Versatile Access to ­Naphthopyranoisoxazolines

Theodoros Liaskopoulos; Stavroula Skoulika; Petros G. Tsoungas; George Varvounis

doi:10.1055/s-2008-1032178

PAPER

Novel Synthesis of Naphthopyranoisoxazoles and Versatile Access to Naphthopyranoisoxazolines

Theodoros Liaskopoulos^a, Stavroula Skoulika^a, Petros G. Tsoungas^b, 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

Abstract

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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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Novel Synthesis of Naphthopyranoisoxazoles and Versatile Access to ­Naphthopyranoisoxazolines

Novel Synthesis of Naphthopyranoisoxazoles and Versatile Access to Naphthopyranoisoxazolines