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

✍ Scribed by Diana T. Patoilo; Artur M. S. Silva; Diana C. G. A. Pinto; Augusto C. Tomé; José A. S. Cavaleiro

Publisher: Journal of Heterocyclic Chemistry
Year: 2007
Tongue: English
Weight: 381 KB
Volume: 44
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570440617

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✦ Synopsis

Abstract

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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%).

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