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- Title
Catalytic Friedel-Crafts/Lactonization Domino Reaction: Facile Access to 3-Hydroxybenzofuran-2-one Scaffold.
- Authors
Vetica, Fabrizio; Pelosi, Alessandra; Gambacorta, Augusto; Loreto, M. Antonietta; Miceli, Martina; Gasperi, Tecla
- Abstract
A valuable Lewis-acid-catalysed domino reaction involving a Friedel-Crafts alkylation of variously substituted phenols followed by a direct lactonization has been successfully developed (22 examples, yields up to 98 %). This protocol tolerates not only opposite electron demand substituents on the starting materials, but also drastic modifications of the alkylating agents, and gives direct access to the corresponding 3-hydroxy-benzofuran-2-ones, which could easily undergo further chemical transformation. The relevance of our method was further confirmed by the straightforward synthesis of rac-BHFF, the recently discovered and extremely promising positive allosteric modulator of the GABAB receptor.
- Subjects
PHENOLS; FRIEDEL-Crafts reaction; LEWIS acids; ALKYLATION; ALKYLATING agents; BENZOFURAN
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 9, p1899
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301686