Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2006, Issue 11, Pages 2558-2569Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200500872
Keywords
2-naphthyl ketones; benzophenones; Diels-Alder reactions; microwave irradiation; benzoxanthones
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Diels-Alder reactions of the 2'-hydroxychalcones 1a-e with ortho-benzoquinodimethane (3) yielded the 3-aryl-1,2,3,4-tetrahydro-2-naphthyl 2-hydroxyphenyl ketones 4a-e in good yields. The dehydrogenation of the cycloadducts 4a-e to 3-aryl-2-naphthyl 2-hydroxyphenyl ketones 5a-e was studied. Good results were obtained when DDQ was used as oxidant and microwave irradiation as energy source. Several benzoxanthone derivatives were also obtained as minor products. Structures of all new compounds were established by extensive NMR studies.
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