Novel enamine derivatives of 5,6-dihydro-2'-deoxyuridine formed in reductive amination of 5-formyl-2'-deoxyuridine

Nucleosides Nucleotides Nucleic Acids. 2008 Sep;27(9):1045-60. doi: 10.1080/15257770802271789.

Abstract

Reductive amination of 5-formyl-3',5'-di-O-acetyl-2'-deoxyuridine with primary amines and sodium triacetoxyborohydride (NaBH(OAc)(3)) afforded novel enamine derivatives of 5,6-dihydro-2'-deoxyuridine as a result of unexpected 1,4-conjugate reduction of intermediate Schiff bases in addition to the secondary amine derivatives of 2'-deoxyuridine, typical 1,2-reduction products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Butylamines / chemistry
  • Deoxyuridine / analogs & derivatives*
  • Deoxyuridine / chemistry
  • Methylamines / chemistry
  • Molecular Structure
  • Schiff Bases / chemistry
  • Spectrophotometry, Ultraviolet

Substances

  • 5,6-dihydro-2'-deoxyuridin-6-yl
  • Butylamines
  • Methylamines
  • Schiff Bases
  • 5-formyl-2'-deoxyuridine
  • methylamine
  • n-butylamine
  • Deoxyuridine