Abstract
2,2-Dimethyl-3-(2-methyl-3-indolyl)cyclopropylacetic acid, its amide and esters, and the corresponding alcohol, viz., the product of ester reduction by LiAlH4, were synthesized. The chemoselectivity of N- and O-alkylation of these compounds was studied. Selective monoalkylation at the nitrogen atom of the heterocycle, O-alkylation to the side chain, or dialkylation at both nucleophilic sites can be carried out under conditions of phase-transfer catalysis. The N-acylation at the indole fragment of nitrile of this acid occurs only under the Vilsmeier—Haak formylation conditions.
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Burakova, E.A., Burchak, O.N. & Chibiryaev, A.M. N- and O-Alkylation of 3-indolylcyclopropylacetic acid derivatives. Russian Chemical Bulletin 51, 1829–1840 (2002). https://doi.org/10.1023/A:1021392216350
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DOI: https://doi.org/10.1023/A:1021392216350