Selective reduction of 1,4-diarylimidazoline-3-oxides to imidazolidin-1-ols and hydroxylamine derivatives

ASUTAY O., Coskun N.

MONATSHEFTE FUR CHEMIE, vol.141, no.8, pp.901-905, 2010 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 141 Issue: 8
  • Publication Date: 2010
  • Doi Number: 10.1007/s00706-010-0344-y
  • Journal Name: MONATSHEFTE FUR CHEMIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.901-905
  • Bursa Uludag University Affiliated: Yes

Abstract

C-2-unsubstituted imidazoline-3-oxides were reduced with NaBH4 in THF to give the corresponding trans-3,5-diarylimidazolidin-1-ols, while under the same conditions C-2-substituted derivatives gave the corresponding ring-chain-ring tautomers. Treatment of the crude reaction mixture from the reduction of C-2-unsubstituted imidazoline-3-oxides with a MeOH-H2O mixture provided reductive C-N bond cleavage to give hydroxylamines, while under the same conditions ring-chain-ring tautomers remained unchanged.