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New Syntheses of Flavones from Diels–Alder Reactions of 2‐Styrylchromones with ortho ‐Benzoquinodimethanes
Author(s) -
S. Silva Artur M.,
G. Silva Ana M.,
Tomé Augusto C.,
S. Cavaleiro José A.
Publication year - 1999
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/(sici)1099-0690(199901)1999:1<135::aid-ejoc135>3.0.co;2-i
Subject(s) - chemistry , cycloaddition , flavones , halogenation , organic chemistry , aryl , aromatization , diels–alder reaction , medicinal chemistry , catalysis , alkyl , chromatography
The first reported cycloaddition reactions of 2‐styrylchromones with ortho ‐benzoquinodimethane afforded 2‐[2‐(3‐aryl‐1,2,3,4‐tetrahydronaphthyl)]chromones. These cycloadducts were converted into the corresponding 2‐[2‐(3‐arylnaphthyl)]chromones (benzoflavone derivatives) by bromination/dehydrobromination processes. These benzoflavone derivatives were also obtained in one‐pot cycloaddition reactions of 2‐styrylchromones with ortho ‐benzoquinodibromomethane.