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.
[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.
Kennedy
April L
AL
Array BioPharma, 3200 Walnut Street, Boulder, Colorado 80301, USA. akennedy@arraybiopharma.com
Fryer
Andrew M
AM
Josey
John A
JA
D001569:Benzodiazepines / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D009570:Nitriles / Q000737:chemistry*; D010879:Piperazines / Q000138:chemical synthesis*; D011108:Polymers; D013056:Spectrophotometry, Ultraviolet
D007202:Indicators and Reagents; D009570:Nitriles; D010879:Piperazines; D011108:Polymers; D001569:Benzodiazepines