Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring-chain tautomerism

Coskun N., Asutay O.

TETRAHEDRON LETTERS, vol.48, no.29, pp.5151-5155, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 48 Issue: 29
  • Publication Date: 2007
  • Doi Number: 10.1016/j.tetlet.2007.05.058
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5151-5155
  • Bursa Uludag University Affiliated: Yes


Imidazolin-3-oxides I were reduced with NaBH4 in THF at reflux to give the corresponding 2,3,5-triarylimidazolidin-l-oles 2, which are proved to be in a ring-chain-ring tautomeric equilibrium with N-2-aminoethyl nitrones 3 and 3,5,6-triphenyl-1,2,5-oxadiazinanes 4. The ratios of the ring and chain form are determined by the substituent at the reaction centre and can be described by the equation logK(x) = p sigma(+) + logK(x=H). These are the first examples of a novel three-component ring-chain-ring tautomeric equilibrium characterized by a Hammett-type equation. The stability of the ring form was favoured by electron-withdrawing substituents. Treatment of the equilibrium mixture of 2, 3 and 4 with phenylisocyanate in refluxing toluene gives selectively the corresponding O-carbamoylated imidazolidines 5; cis-5 was shown to isomerize to trans-5 on heating. (C) 2007 Elsevier Ltd. All rights reserved.