Condensation of 2-ethoxypropenal with diaminoethylene in different solvents (CHCl3, MeCN, H2O, DMSO) at room temperature gives an equilibrium mixture (1:1–1.5) of tautomeric 2-(1′-ethoxyvinyl)-1,3-imidazolidine and 2-aminoethylimine of 2-ethoxypropenal as well as 1,2-bis(2′-ethoxypropenyl-ideneamino)ethylene. The latter is readily prepared in quantitative yield using a twofold excess of the aldehyde. 1H NMR was used to demonstrate the effect of heating on the dynamics of the ring-chain tautomeric equilibrium. Reaction of the 2-alkoxypropenals with N-methyl- and N,N′-diphenyl-1,2-diaminoethylenes and with N-phenylaminoethanol gives only the corresponding substituted imidazolidines in 43–95% yield.
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Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov in his 70th jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1809–1815, December, 2008.
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Keiko, N.A., Vchislo, N.V., Stepanova, L.G. et al. Condensation of 2-alkoxypropenals with N,N- and N,O-1,2-binucleophiles. A route to 2-(1′-alkoxyvinyl)imidazo-lidines and -oxazolidines. Chem Heterocycl Comp 44, 1466–1471 (2008). https://doi.org/10.1007/s10593-009-0213-y
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DOI: https://doi.org/10.1007/s10593-009-0213-y