Abstract
A number of amides of indole ketoacids are synthesized. 3-Carboxyacylindoles can be converted to the corresponding enol-lactones by treatment with acetic anhydride or acetyl chloride. Reaction of the lactones with ammonia or amines involves lactone ring opening, and this makes it possible to prepare some N-substituted or unsubstituted ketoacid amides. Deacylation can occur in the action of strong bases or high temperatures on indoleketoacids. Reaction of 2-(indolyl-3') benzoic acid with dimethyl sulfate proceeds in two ways: the NH group is methylated, and there is conversion to the corresponding indolenine, with subsequent methylation of the enol.
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Kost, A.N., Eraksina, V.N., Vinogradova, E.V. et al. The chemistry of indole. Chem Heterocycl Compd 2, 165–168 (1967). https://doi.org/10.1007/BF00480962
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DOI: https://doi.org/10.1007/BF00480962