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- Title
Reaction of dialkyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates with aliphatic amines.
- Authors
Gein, V. L.; Nosova, N. V.; Prusakova, A. S.; Vakhrin, M. I.; Kriven'ko, A. P.
- 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-(1 H-indol-3-yl)ethylamino]-6-methyl-2-phenylcyclohexa-3,5-diene-1,3-dicarboxylate, presumably due to basic properties of the indole nitrogen atom.
- Subjects
CHEMICAL reactions; AMINES; ALIPHATIC compounds; CARBON compounds; HYDROXYLATION; PHYSICAL organic chemistry
- Publication
Russian Journal of General Chemistry, 2008, Vol 78, Issue 12, p2357
- ISSN
1070-3632
- Publication type
Article
- DOI
10.1134/S1070363208120116