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Application of the anionic homologous Fries‐rearrangement to the synthesis of 3‐alkylbenzofuran‐2(3 H )‐ones
Author(s) -
Azzena Ugo,
Pisano Luisa,
Pittalis Mario
Publication year - 2008
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1437
Subject(s) - chemistry , fries rearrangement , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , catalysis
We have developed an effective organometallic‐based procedure allowing the employment of 2‐methylphenols as easily available starting materials in the synthesis of 3‐alkylbenzofuran‐2(3 H )‐ones. The first step of this protocol, an anionic homologous Fries‐rearrangement, afforded 2‐(2‐ tert ‐butyldimethylsilyloxyaryl)acetamides, which were selectively metalated and monoalkylated at the benzylic position. Acidic work‐up of crude products afforded the desired heterocycles in satisfactory overall yields. Copyright © 2008 John Wiley & Sons, Ltd.