A new resin-bound universal isonitrile for the Ugi 4CC reaction: preparation and applications to the synthesis of 2,5-diketopiperazines and 1,4-benzodiazepine-2,5-diones

Org Lett. 2002 Apr 4;4(7):1167-70. doi: 10.1021/ol0256015.

Abstract

[reaction: see text] The preparation and synthetic applications of a novel resin-bound isonitrile are described. The resin is an example of a novel convertible isonitrile that can be utilized in the Ugi multicomponent reaction. Base-activation of the resin-bound Ugi product results in cleavage via formation of a N-acyloxazolidone that is then trapped as a carboxylic acid ester. This resin and the methodology described are suitable for synthesizing diversity libraries of 2,5-diketopiperazines and 1,4-benzodiazepine-2,5-diones.

MeSH terms

  • Benzodiazepines / chemical synthesis*
  • Chromatography, High Pressure Liquid
  • Indicators and Reagents
  • Mass Spectrometry
  • Nitriles / chemistry*
  • Piperazines / chemical synthesis*
  • Polymers
  • Spectrophotometry, Ultraviolet

Substances

  • Indicators and Reagents
  • Nitriles
  • Piperazines
  • Polymers
  • Benzodiazepines