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 |
| 本文献已被 SpringerLink 等数据库收录！ |
|
