Application of the Anionic Homologous Fries-Rearrangement to the Synthesis of 3-Alkylbenzofuran-2(3H)-ones
Articolo
Data di Pubblicazione:
2008
Citazione:
Application of the Anionic Homologous Fries-Rearrangement to the Synthesis of 3-Alkylbenzofuran-2(3H)-ones / Azzena, U.G., Pisano, L., Mario, P.. - In: APPLIED ORGANOMETALLIC CHEMISTRY. - ISSN 0268-2605. - 22:(2008), pp. 523-528. [10.1002/aoc.1437]
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 yields
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
Tipologia CRIS:
1.1 Articolo in rivista
Keywords:
benzofuran-2(3H)-ones; Fries rearrangement; organolithiums
Elenco autori:
Azzena, Ugo Gavino; Pisano, Luisa; Mario, Pittalis
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