Organic Brønsted acid‐catalyzed cycloadditions of o‐quinone methides with 1, 3‐dicarbonlys: Facile access to xanthenones and chromanones

The in‐situ generation of o‐quinone methides and their inverse‐electron‐demand Diels–Alder reaction in the presence of pentacarboxycyclopentadiene—an organic Brønsted acid—has been reported. The synthesis of xanthenones and chromanones in good to excellent yields from the [4 + 2] cycloaddition of qu...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2021-10, Vol.58 (10), p.1971-1982
Main Authors: Thoppe Sivakumar, Priyadarshini, Puthiyaparambath, Sharathna, Suresh Varma, Sanjay, Parameswaran, Sasikumar, Kokkuvayil Vasu, Radhakrishnan
Format: Article
Language:English
Subjects:
Cycloaddition
Diels-Alder reactions
Quinones
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Summary:The in‐situ generation of o‐quinone methides and their inverse‐electron‐demand Diels–Alder reaction in the presence of pentacarboxycyclopentadiene—an organic Brønsted acid—has been reported. The synthesis of xanthenones and chromanones in good to excellent yields from the [4 + 2] cycloaddition of quinone methides with 1, 3‐dicarbonyls and Meldrum's acid has been accomplished. The development of this method helps in generating a number of biologically potent heterocycles with medicinal applications.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4323