Novel safety-catch linker and its application with a Ugi/De- BOC/cyclization (UDC) strategy to access carboxylic acids, 1,4- benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones

Christopher Hulme, John Peng, George Morton, Joseph M. Salvino, Tim Herpin, Richard Labaudiniere

Research output: Contribution to journalArticle

124 Citations (Scopus)

Abstract

This communication reveals the synthesis and application of a novel resin bound isonitrile. The resin is an example of a novel safety-catch linker which upon BOC-activation can be resin cleaved with a variety of nucleophiles. Use of this polymer supported isonitrile in the Ugi multi- component reaction (MCR), followed by resin clipping and cyclization allows access to diverse arrays of 1,4-benzodiazepine-2,5-diones, diketopiperazines and ketopiperazines respectively. The methoxide safety-catch clipping strategy and subsequent solution phase cyclization offers similar advantages to a traceless linker.

Original languageEnglish (US)
Pages (from-to)7227-7230
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number40
StatePublished - Oct 1 1998
Externally publishedYes

Fingerprint

Diketopiperazines
Cyclization
Carboxylic Acids
Resins
Safety
Polymers
Nucleophiles
Chemical activation
Bz-423
Communication

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel safety-catch linker and its application with a Ugi/De- BOC/cyclization (UDC) strategy to access carboxylic acids, 1,4- benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones. / Hulme, Christopher; Peng, John; Morton, George; Salvino, Joseph M.; Herpin, Tim; Labaudiniere, Richard.

In: Tetrahedron Letters, Vol. 39, No. 40, 01.10.1998, p. 7227-7230.

Research output: Contribution to journalArticle

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