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Diels–Alder Reactions of 2′‐Hydroxychalcones with ortho ‐Benzoquino‐dimethane: A New Synthesis of 3‐Aryl‐2‐naphthyl 2‐Hydroxyphenyl Ketones
Author(s) -
Brito Cristela M.,
Pinto Diana C. G. A.,
Silva Artur M. S.,
Silva Ana M. G.,
Tomé Augusto C.,
Cavaleiro José A. S.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500872
Subject(s) - chemistry , dehydrogenation , aryl , microwave irradiation , ketone , medicinal chemistry , organic chemistry , diels–alder reaction , catalysis , alkyl
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)