CONDENSATION OF 2-ALKOXYPROPENALS WITH N,N- AND N,O-1,2-BINUCLEOPHILES. A ROUTE TO 2-(1'-ALKOXYVINYL)IMIDAZOLIDINES AND -OXAZOLIDINES

Authors

  • Н. А. Кейко A. E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences, Irkutsk 664033
  • Н. В. Вчисло A. E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences, Irkutsk 664033
  • Л. Г. Степанова A. E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences, Irkutsk 664033
  • Л. И. Ларина A. E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences, Irkutsk 664033
  • Ю. А. Чувашев A. E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences, Irkutsk 664033
  • Е. А. Фунтикова A. E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences, Irkutsk 664033

DOI:

https://doi.org/10.1007/7297

Keywords:

2-alkoxypropenals, 1, 2-diaminoethylenes, imidazolidines, oxazolidines, condensation, tautomerism

Abstract

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.

How to Cite
Keiko, N. A.; Vchislo, N. V.; Stepanova, L. G.; Larina, L. I.;
Chuvashev, Yu. A.; Funtikova, E. A.  Chem. Heterocycl. Compd. 2008, 44, 1466. [Khim. Geterotsikl. Soedin. 2008, 1809.]

For this article in the English edition see DOI 10.1007/s10593-009-0213-y

 

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Published

2023-01-05

Issue

No. 12 (2008)

Section

Original Papers