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

17 Citations (Scopus)

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 2012

Fingerprint

Cyanides
Aniline
aniline
Scaffolds
routes
Phenylenediamines
preparation
Condensation reactions
Microwave irradiation
Microwaves
reagents
condensation
microwaves
irradiation
ethyl glyoxalate

Keywords

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

ASJC Scopus subject areas

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

Cite this

Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes. / Xu, Zhigang; Shaw, Arthur Y.; Nichol, Gary S.; Cappelli, Alexandra P.; Hulme, Christopher.

In: Molecular Diversity, Vol. 16, No. 3, 08.2012, p. 607-612.

Research output: Contribution to journalArticle

Xu, Zhigang ; Shaw, Arthur Y. ; Nichol, Gary S. ; Cappelli, Alexandra P. ; Hulme, Christopher. / Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes. In: Molecular Diversity. 2012 ; Vol. 16, No. 3. pp. 607-612.
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