Abstract
Reactions of 2-alkoxypropenals with 2-aminoalkanols afforded tautomeric mixtures of previously unknown 2-(1-alkoxyvinyl)oxazolidines and imino alcohols. The condensation takes 2 h at room temperature (89-100%) or 1-5 min under microwave irradiation. The tautomeric equilibrium shifts toward the open-chain structure with increase in the solvent polarity (CDCl3, CD2OD, DMSO-d 6, D2O) and temperature. The presence of substituents in the oxazolidine ring raises the stability of the cyclic tautomer.
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Keiko, N.A., Funtikova, E.A., Stepanova, L.G. et al. Synthesis of 2-(1-Alkoxyvinyl)oxazolidines by Condensation of 2-Alkoxypropenals with 2-Aminoalkanols and Ring-Chain Tautomerism of the Products. Russian Journal of Organic Chemistry 39, 1477–1483 (2003). https://doi.org/10.1023/B:RUJO.0000010565.77155.ab
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DOI: https://doi.org/10.1023/B:RUJO.0000010565.77155.ab