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Synthesis of 5‐Hydroxy‐2‐(naphth‐2‐yl)chromone derivatives
Author(s) -
Patoilo Diana T.,
Silva Artur M. S.,
Pinto Diana C. G. A.,
Tomé Augusto C.,
Cavaleiro José A. S.
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440617
Subject(s) - chemistry , dehydrogenation , microwave irradiation , chromone , sulfur dioxide , medicinal chemistry , thiophene , sulfur , aryl , organic chemistry , photochemistry , alkyl , catalysis
The Diels‐Alder reaction of 5‐hydroxy‐2‐styrylchromones with ortho ‐benzoquinodimethane, generated “ in situ ” by thermal extrusion of sulfur dioxide from 1,3‐dihydrobenzo[ c ]thiophene 2,2‐dioxide, leads to 2‐(3‐aryl‐1,2,3,4‐tetrahydronaphth‐2‐yl)‐5‐hydroxychromones. These cycloadducts were dehydrogenated with DDQ, using classical thermal reflux conditions and microwave irradiation, affording the corresponding 2‐(3‐arylnaphth‐2‐yl)‐5‐hydroxychromones in high yields (48‐96%).