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Chemistry of Heterocyclic Compounds

, Volume 51, Issue 10, pp 940–943 | Cite as

The first example of an unusual rearrangement in the van Leusen imidazole synthesis

  • Mokhtar FodiliEmail author
  • Bellara Nedjar-Kolli
  • Marc Vedrenne
  • Nathalie Saffon-Merceron
  • Christian Lherbet
  • Pascal HoffmannEmail author
Article

The synthesis of an 1,4-disubstituted 5-methylimidazole is reported by reacting toluenesulfonylmethyl isocyanide with an enaminic tautomeric form of a secondary ketimine in the presence of catalytic amounts of bismuth(III) triflate. A possible mechanism involving a tosyl substitution on the imidazoline intermediate is proposed. This work represents a novel application for the versatile reagent toluenesulfonylmethyl isocyanide that expands its use to the preparation of imidazole starting from ketimine compounds.

Keywords

bismuth(III) triflate enamine imidazole ketimine TosMIC 

Supplementary material

10593_2015_1801_MOESM1_ESM.pdf (1.1 mb)
Supporting material (PDF 1117 kb)

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Mokhtar Fodili
    • 1
    Email author
  • Bellara Nedjar-Kolli
    • 2
  • Marc Vedrenne
    • 3
  • Nathalie Saffon-Merceron
    • 3
  • Christian Lherbet
    • 4
  • Pascal Hoffmann
    • 4
    Email author
  1. 1.Université Ziane Achour, Laboratoire de Chimie Organique & Substances NaturellesDjelfaAlgerie
  2. 2.Université des Sciences et de la Technologie Houari Boumediene, Laboratoire de Chimie OrganiqueAlgerAlgérie
  3. 3.Université de Toulouse, UPS, Institut de Chimie de Toulouse, ICT FR 2599Toulouse cedex 9France
  4. 4.Université de Toulouse, UPS, LSPCMIB (Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique), UMR CNRS 5068Toulouse cedex 9France

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