Revisit to the reaction of o-phenylene diamine with thiosemicarbazide to give benzimidazole-2-thione rather than benzotriazine-2-thione and its glycosylation

Nucleosides Nucleotides Nucleic Acids. 2010 Sep;29(9):698-706. doi: 10.1080/15257770.2010.501777.

Abstract

Reaction of o-phenylene diamine with thiosemicarbazide did not give benzotriazine-2-thione 2 as reported, although the product was found to be benzimidazole-2-thione 3. Glycosylation of 3 with acetobromo sugars 4a-4b gave the respective thioglycosides 7a-7d in addition to minor products of the nucleosides 8a and 8b, in the case of the gluco- and galacto-analogs, respectively. The regioselectivity of glycosylation reaction has been investigated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemistry*
  • Glycosides / chemistry
  • Glycosylation
  • Magnetic Resonance Spectroscopy
  • Phenylenediamines / chemistry*
  • Semicarbazides / chemistry*
  • Thiones / chemistry*
  • Triazines / chemistry*

Substances

  • Benzimidazoles
  • Glycosides
  • Phenylenediamines
  • Semicarbazides
  • Thiones
  • Triazines
  • benzotriazine-2-thione
  • benzimidazoline-2-thione
  • thiosemicarbazide
  • 1,2-diaminobenzene