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.
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. |
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/11590/115477 |
Appare nelle tipologie: | 1.1 Articolo in rivista |