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(3H)-ones. The first step of this protocol, an anionic homologous Fries-rearrangement, afforded 2-(2-tert-butyldimethylsilyloxyaryl)acetamides, which were selectively metalated andmonoalkylated at the benzylic position. Acidic work-up of crude products afforded the desired heterocycles in satisfactory overall yields
Application of the Anionic Homologous Fries-Rearrangement to the Synthesis of 3-Alkylbenzofuran-2(3H)-ones / Azzena, Ugo Gavino; Pisano, Luisa; Mario, Pittalis. - In: APPLIED ORGANOMETALLIC CHEMISTRY. - ISSN 0268-2605. - 22:(2008), pp. 523-528. [10.1002/aoc.1437]
Application of the Anionic Homologous Fries-Rearrangement to the Synthesis of 3-Alkylbenzofuran-2(3H)-ones
AZZENA, Ugo Gavino;PISANO, Luisa;
2008-01-01
Abstract
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(3H)-ones. The first step of this protocol, an anionic homologous Fries-rearrangement, afforded 2-(2-tert-butyldimethylsilyloxyaryl)acetamides, which were selectively metalated andmonoalkylated at the benzylic position. Acidic work-up of crude products afforded the desired heterocycles in satisfactory overall yieldsI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
