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THE FIRST EXAMPLE OF AN UNUSUAL REARRANGEMENT IN THE VAN LEUSEN IMIDAZOLE SYNTHESIS

Mokhtar Fodili, Bellara Nedjar-Kolli, Marc Vedrenne, Nathalie Saffon-Merceron, Christian Lherbet, Pascal Hoffmann
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Abstract


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.

How to Cite
Fodili, M.; Nedjar-Kolli, B.; Vedrenne, M.; Saffon-Merceron, N.; Lherbet, C.; Hoffmann, P. Chem. Heterocycl. Compd. 2015, 51, 940. [Khim. Geterotsikl. Soedin. 2015, 51, 940.]

For this article in the English edition see DOI 10.1007/s10593-015-1801-7


Keywords


TosMIC; imidazole; ketimine; enamine; bismuth(III) triflate

Full Text: PDF Supplementary File(s): Supporting information (1MB)


 

 

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