J. P. Sanchez, R. Parcell
Sep 1, 1990
Citations
0
Influential Citations
6
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The reaction of 2-bromo-1-(1H-indol-3-yl)-2-methyl-1-propanone (1) and 2-bromo-1-(1-methyl-1H-indol-3-yl)-2-methyl-1-propanone (2) with primary amines proceeds in good yields to produce rearranged amides by a proposed pseudo-Favorskii mechanism. These amides in turn can either be reduced to produce β-substituted tryptamines or hydrolyzed to produce substituted indole-3-acetic acids. When the reaction is carried out using bulky primary or secondary amines, β-aminoketones are produced by elimination of hydrogen bromide followed by Michael addition. When hindered secondary amines or tertiary amines are used, elimination to the α,β-unsaturated ketones occurs.