Selective reduction of 1,4-diarylimidazoline-3-oxides to imidazolidin-1-ols and hydroxylamine derivatives |
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Authors: | Oktay Asutay and Necdet Co?kun |
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Institution: | (1) Department of Chemistry, Muratlı Vocational School, Namık Kemal University, Muratlı-Tekirdağ, Turkey;(2) Department of Chemistry, Uludağ University, 16059 Bursa, Turkey |
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Abstract: | 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. |
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