Abstract
Benzylamine, phenethylamine, and homoveratrylamine reacted with dialkyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates at the endocyclic carbonyl group with conservation of the enolic hydroxy group to give dialkyl 4-alkylamino-2-aryl-6-hydroxy-6-methylcyclohex-3-ene-1,3-dicarboxylates. The reaction of dimethyl 4-hydroxy-4-methyl-6-oxo-2-phenylcyclohexane-1,3-dicarboxylate with tryptamine was accompanied by dehydration with formation of dimethyl 4-[2-(1H-indol-3-yl)ethylamino]-6-methyl-2-phenylcyclohexa-3,5-diene-1,3-dicarboxylate, presumably due to basic properties of the indole nitrogen atom.
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Original Russian Text © V.L. Gein, N.V. Nosova, A.S. Prusakova, M.I. Vakhrin, A.P. Kriven’ko, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 12, pp. 2011–2016.
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Gein, V.L., Nosova, N.V., Prusakova, A.S. et al. Reaction of dialkyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates with aliphatic amines. Russ J Gen Chem 78, 2357–2362 (2008). https://doi.org/10.1134/S1070363208120116
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DOI: https://doi.org/10.1134/S1070363208120116