Solid-phase traceless synthesis of selected nitrogen-containing heterocyclic compounds. The encore technique for directed sorting of modular solid support

Viktor Krchňák, Jennifer Smith, Josef Vágner

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminobenzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compound precursors were assembled on a solid-phase support derivatized with either a benzylamine or a benzhydrylamine linker. Exposure to an acidic reagent caused cleavage of the C(benzyl)-N(aniline) bond, releasing the product with only a hydrogen atom on the descending nitrogen. The Encore technique for directed sorting on SynPhase Lanterns has been developed and applied to combinatorial synthesis of generic drug discovery libraries.

Original languageEnglish (US)
Pages (from-to)1078-1106
Number of pages29
JournalCollection of Czechoslovak Chemical Communications
Volume66
Issue number7
DOIs
StatePublished - Dec 1 2001
Externally publishedYes

Keywords

  • Benzimidazoles
  • Benzylamine linkers
  • Combinatorial libraries
  • Heterocycles
  • Quinoxalines
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Chemistry(all)

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