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].
Titolo: | Catalytic Friedel–Crafts/Lactonization Domino Reaction: Facile Access to 3-Hydroxybenzofuran-2-one Scaffold | |
Autori: | ||
Data di pubblicazione: | 2014 | |
Rivista: | ||
Citazione: | 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]. | |
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. | |
Handle: | http://hdl.handle.net/11590/137736 | |
Appare nelle tipologie: | 1.1 Articolo in rivista |