4-Amino-2-methylbenzofurans are quantitatively converted to 4-hydroxy-2-methylindoles in acidic medium. The rearrangement mechanism involves the ring opening of the furan ring to produce an intermediate carbocation, which undergoes ring closure to the indole system. Isomerization takes place only in the presence of a methyl substituent in 2 position.
Isomerization of 4-Aminobenzofurans to 4-Hydroxyindoles.
CHILIN, ADRIANA;GUIOTTO, ADRIANO
1998
Abstract
4-Amino-2-methylbenzofurans are quantitatively converted to 4-hydroxy-2-methylindoles in acidic medium. The rearrangement mechanism involves the ring opening of the furan ring to produce an intermediate carbocation, which undergoes ring closure to the indole system. Isomerization takes place only in the presence of a methyl substituent in 2 position.
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