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Catalytic Friedel–Crafts/Lactonization Domino Reaction: Facile Access to 3‐Hydroxybenzofuran‐2‐one Scaffold
Author(s) -
Vetica Fabrizio,
Pelosi Alessandra,
Gambacorta Augusto,
Loreto M. Antonietta,
Miceli Martina,
Gasperi Tecla
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301686
Subject(s) - chemistry , friedel–crafts reaction , benzofuran , catalysis , domino , lewis acids and bases , combinatorial chemistry , alkylation , phenols , scaffold , cascade reaction , organic chemistry , medicine , biomedical engineering
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 GABA B receptor.