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Synthesis 2008(5): 711-718
DOI: 10.1055/s-2008-1032178
DOI: 10.1055/s-2008-1032178
PAPER
© Georg Thieme Verlag Stuttgart · New York
Novel Synthesis of Naphthopyranoisoxazoles and Versatile Access to Naphthopyranoisoxazolines
Weitere Informationen
Received
20 November 2007
Publikationsdatum:
18. Februar 2008 (online)
Publikationsverlauf
Publikationsdatum:
18. Februar 2008 (online)
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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