Synthesis of 5‐Hydroxy‐2‐(naphth‐2‐yl)chromone derivatives | Zendy

Patoilo Diana T. | Zendy; Silva Artur M. S. | Zendy; Pinto Diana C. G. A. | Zendy; Tomé Augusto C. | Zendy; Cavaleiro José A. S. | Zendy

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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%).

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