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

ASUTAY O., Coskun N.

MONATSHEFTE FUR CHEMIE, cilt.141, sa.8, ss.901-905, 2010 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 141 Sayı: 8
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1007/s00706-010-0344-y
  • Dergi Adı: MONATSHEFTE FUR CHEMIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.901-905
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

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.