Abstract
2-Acylindoles and 2-acylindole-3-carboxylic acids are readily alkylated at the nitrogen atom by haloalkanes in a superbasic medium (DMSO + NaOH). For the carboxylic acids, this reaction may proceed either entirely at the nitrogen atom, or at both the the nitrogen atom and the carboxyl group, depending on the content of water in the medium and the alkali -haloalkane ratio.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 472–482, April, 1996.
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Rekhter, M.A. Syntheses of 1-alkyl-2-acylindoles, 1-alkyl-2-acylindole-3-carboxylic acids, and their esters, in superbasic media. Chem Heterocycl Compd 32, 408–417 (1996). https://doi.org/10.1007/BF01165901
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DOI: https://doi.org/10.1007/BF01165901