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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Notes

  1. It should be noted that the imidazole C-8 carbon signal is not visible in the 1D 13C J-MOD NMR spectrum because the two nitrogen atoms cause broadening and attenuation of its signal, however the signal is clearly visible in the HSQC spectrum.

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Authors and Affiliations

  1. Université Ziane Achour, Laboratoire de Chimie Organique & Substances Naturelles, Djelfa, Algerie

    Mokhtar Fodili

  2. Université des Sciences et de la Technologie Houari Boumediene, Laboratoire de Chimie Organique, Alger, Algérie

    Bellara Nedjar-Kolli

  3. Université de Toulouse, UPS, Institut de Chimie de Toulouse, ICT FR 2599, 118 route de Narbonne, 31062, Toulouse cedex 9, France

    Marc Vedrenne & Nathalie Saffon-Merceron

  4. Université de Toulouse, UPS, LSPCMIB (Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique), UMR CNRS 5068, 118 route de Narbonne, 31062, Toulouse cedex 9, France

    Christian Lherbet & Pascal Hoffmann

Authors
  1. Mokhtar Fodili
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  2. Bellara Nedjar-Kolli
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  3. Marc Vedrenne
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  4. Nathalie Saffon-Merceron
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  5. Christian Lherbet
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  6. Pascal Hoffmann
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Corresponding authors

Correspondence to Mokhtar Fodili or Pascal Hoffmann.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 940–943

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Fodili, M., Nedjar-Kolli, B., Vedrenne, M. et al. The first example of an unusual rearrangement in the van Leusen imidazole synthesis. Chem Heterocycl Comp 51, 940–943 (2015). https://doi.org/10.1007/s10593-015-1801-7

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  • DOI: https://doi.org/10.1007/s10593-015-1801-7

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