Some Observations on the Formation of 1-Hydroxyindoles in the Leimgruber-Batcho Indole Synthesis
The factors influencing the formation of 1-hydroxyindoles in the catalytic hydrogenation of β-dimethylamino-2-nitrostyrenes (Leimgruber-Batcho indole synthesis) have been investigated.Significant amounts of 1-hydroxyindoles were obtained only when the β-dimethylamino-2-nitrostyrene was substituted with an electron-withdrawing group at the 5 or 6 position.The proportion of 1-hydroxyindole formed relative to the normal indole product was found to increase as both the amount of catalyst and hydrogen pressure were decreased.
Clark, Robin D.,Repke, David B.
p. 121 - 125
(2007/10/02)
The chemistry of indoles. XIII. Syntheses of substituted indoles carrying an amino, nitro, methoxycarbonyl, or benzyloxy group at the 4-position and their 1-hydroxy derivatives
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Somei,Inoue,Tokutake,et al.
p. 726 - 738
(2007/10/02)
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