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N- and O-Alkylation of 3-indolylcyclopropylacetic acid derivatives
Authors:Burakova  E A  Burchak  O N  Chibiryaev  A M
Institution:(1) Department of Natural Sciences, Novosibirsk State University, 2 ul. Pirogova, 630090 Novosibirsk, Russian Federation;(2) Siberian Branch of the Russian Academy of Sciences, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 prosp. Akad. Lavrent"eva, 630090 Novosibirsk, Russian Federation
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.
Keywords:Fischer indole synthesis  3-indolylcyclopropylacetic acid and its esters  nitriles  amides  hydrolysis  N-alkylation and N-sulfonylation of indoles  O-alkylation of carboxylic acids and alcohols  phase-transfer catalysis  Vilsmeier—  Haak reaction
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