Synthesis of Imidazoles from Ketimines Using Tosylmethyl Isocyanide (TosMIC) Catalyzed by Bismuth Triflate

Mokhtar      Fodili; Bellara      Nedjar-Kolli; Bernard      Garrigues; Christian      Lherbet; Pascal      Hoffmann

doi:10.2174/157017809788681275

Abstract

The preparation of a series of 1,5-disubstituted-4-methyl imidazoles is reported, based on an unprecedented reaction between an acetimine and TosMIC in the presence of tert-butylamine and catalytic amounts of bismuth(III) triflate. The mechanism is believed to involve formation of an imidazoline intermediate, followed by the methyl group migration, and subsequent aromatization to the imidazole ring.

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Letters in Organic Chemistry

Title: Synthesis of Imidazoles from Ketimines Using Tosylmethyl Isocyanide (TosMIC) Catalyzed by Bismuth Triflate

Volume: 6 Issue: 5

Author(s): Mokhtar Fodili, Bellara Nedjar-Kolli, Bernard Garrigues, Christian Lherbet and Pascal Hoffmann

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Abstract: The preparation of a series of 1,5-disubstituted-4-methyl imidazoles is reported, based on an unprecedented reaction between an acetimine and TosMIC in the presence of tert-butylamine and catalytic amounts of bismuth(III) triflate. The mechanism is believed to involve formation of an imidazoline intermediate, followed by the methyl group migration, and subsequent aromatization to the imidazole ring.

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Fodili Mokhtar, Nedjar-Kolli Bellara, Garrigues Bernard, Lherbet Christian and Hoffmann Pascal, Synthesis of Imidazoles from Ketimines Using Tosylmethyl Isocyanide (TosMIC) Catalyzed by Bismuth Triflate, Letters in Organic Chemistry 2009; 6 (5) . https://dx.doi.org/10.2174/157017809788681275