Synthesis of 5-Hydroxy-2-(naphth-2-yl)chromone derivatives

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 dehydrogenat...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2007-11, Vol.44 (6), p.1345-1350
Main Authors: Patoilo, Diana T., Silva, Artur M. S., Pinto, Diana C. G. A., Tomé, Augusto C., Cavaleiro, José A. S.
Format: Article
Language:English
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Summary: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%).
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570440617