Abstract
A method for the monoalkylation of nitroacetic ester with gramine in the presence of triethylamine is proposed. The basis of the method is the difference in the acidity of the nitroacetic acid ester and its monoalkylation product. The synthesis of β-(3-indolyl)-β-R-α-nitropropionic acid esters (R=Me, Ph), which are precursors of β-substituted tryptophans, was accomplished for the first time by alkylation of nitroacetic ester with indole Mannich bases containing alkyl or aryl substituents in the methylene group.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 780–784, June, 1978.
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Erofeev, Y.V., Velezheva, V.S., Genkina, N.K. et al. Introduction of 3-indolylmethyl residues in nitroacetic acid esters. Chem Heterocycl Compd 14, 637–641 (1978). https://doi.org/10.1007/BF00481137
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DOI: https://doi.org/10.1007/BF00481137