Synthesis of tetrahydro-1,4-benzodiazepine-2-ones on hydrophilic polyamide SynPhase lanterns

J Comb Chem. 2003 Mar-Apr;5(2):166-71. doi: 10.1021/cc020057c.

Abstract

Solid-phase synthesis is greatly dependent on the solid support. Here, we report the use of a new hydrophilic grafted surface on SynPhase lanterns in solid-phase organic chemistry. A convenient and facile solid-phase synthesis of disubstituted 1,4-benzodiazepine-2-ones on polyamide SynPhase lanterns is described. The key step of the synthesis involved a reduction-cyclization of a nitroaryl methyl ester with a mixture of tin(II) chloride dihydrate and ammonium acetate in water and ethanol at elevated temperature to give the desired target compounds. A library of 21 disubstituted 1,4-benzodiazepine-2-ones was prepared.

MeSH terms

  • Benzodiazepinones / chemical synthesis*
  • Chromatography, High Pressure Liquid
  • Indicators and Reagents
  • Nylons / chemical synthesis*
  • Nylons / chemistry
  • Polystyrenes / chemistry

Substances

  • Benzodiazepinones
  • Indicators and Reagents
  • Nylons
  • Polystyrenes