Abstract
Reaction of triacetonamine with ethyl cyanoacetate and ammonium acetate gives, in addition to the normal Knoevenagel reaction product (2,2,6,6-tetramethyl-4-ethoxycarbonylcyanomethylenepiperidine), its conversion product 3-cyano-4-(β,β-dimethylvinyl)-6,6-dimethyl-Δ3-dehydro-2-piperidone. Acid hydrolysis of the latter gives a dihydro-α-pyrone derivative. The mechanism of the formation of the new compounds is discussed, and their structures are proved by their NMR and mass spectra.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 5, pp. 642–646, May, 1970.
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Nikitskaya, E.S., Levkoeva, E.I., Puchkov, V.A. et al. Investigation of the reaction products of triacetonamine and ethyl cyanoacetate under knoevenagel reaction conditions. Chem Heterocycl Compd 6, 592–596 (1970). https://doi.org/10.1007/BF00500681
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DOI: https://doi.org/10.1007/BF00500681