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.

Gasperi T, Vetica F, Pelosi A, Gambacorta A, Loreto M A, & Miceli M (2014). Catalytic Friedel–Crafts/Lactonization Domino Reaction: Facile Access to 3-Hydroxybenzofuran-2-one Scaffold. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1899-1906 [10.1002/ejoc.201301686].

Catalytic Friedel–Crafts/Lactonization Domino Reaction: Facile Access to 3-Hydroxybenzofuran-2-one Scaffold

GASPERI, TECLA;
2014

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.
Gasperi T, Vetica F, Pelosi A, Gambacorta A, Loreto M A, & Miceli M (2014). Catalytic Friedel–Crafts/Lactonization Domino Reaction: Facile Access to 3-Hydroxybenzofuran-2-one Scaffold. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1899-1906 [10.1002/ejoc.201301686].
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11590/137736
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