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

April L. Kennedy,* Andrew M. Fryer, and John A. Josey
Array BioPharma, 3200 Walnut Street, Boulder, Colorado 80301
Org. Lett., 2002, 4 (7), pp 1167–1170
DOI: 10.1021/ol0256015
Publication Date (Web): March 7, 2002
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, akennedy@arraybiopharma.com

Abstract

Abstract Image

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.

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History

  • Published In Issue April 04, 2002
  • Received January 22, 2002

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