Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes

Zhigang Xu, Arthur Y. Shaw, Gary S. Nichol, Alexandra P. Cappelli, Christopher Hulme

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

Concise routes to five pharmacologically relevant bis-heterocyclic scaffolds are described. Significant molecular complexity is generated in a mere two synthetic operations enabling access to each scaffold. Routes are often improved by microwave irradiation and all utilize isocyanide-based multi-component reaction methods to incorporate the required diversity elements. Common reagents in all initial condensation reactions include 2-(N-Boc-amino)-phenyl-isocyanide 1, mono-Boc-phenylenediamine 2 and ethyl glyoxalate 3.

Original languageEnglish (US)
Pages (from-to)607-612
Number of pages6
JournalMolecular Diversity
Volume16
Issue number3
DOIs
StatePublished - Aug 1 2012

Keywords

  • Benzimidazole-quinoxalines
  • Bis-benzimidazoles
  • Dihydroquinoxalinone
  • Multi-component reactions (MCRs)

ASJC Scopus subject areas

  • Catalysis
  • Information Systems
  • Molecular Biology
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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