A New Methodology to Prepare 2-Halogenoimidazoles via a N-THP Protection

Sylvain      Rault; Nicolas      Primas; Alexandre      Bouillon; Jean-Charles      Lancelot; Jana   Sopkova-de Oliveira   Santos; Jean-François      Lohier

doi:10.2174/157017808783330252

Abstract

A straightforward access to 2-halogenoimidazoles via a N-THP protection was described in this paper. The NTHP protecting group is easily introduced by reaction of 2-chloro-THP with imidazole. Lithiation followed by reaction with an appropriate electrophile affords 2-halogeno N-THP derivatives. The THP protecting group is then cleaved to get the title compounds in good to high yields.

Keywords: Imidazole, THP, lithiation, halogenation

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Letters in Organic Chemistry

Title: A New Methodology to Prepare 2-Halogenoimidazoles via a N-THP Protection

Volume: 5 Issue: 1

Author(s): Sylvain Rault, Nicolas Primas, Alexandre Bouillon, Jean-Charles Lancelot, Jana Sopkova-de Oliveira Santos and Jean-François Lohier

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Keywords: Imidazole, THP, lithiation, halogenation

Abstract: A straightforward access to 2-halogenoimidazoles via a N-THP protection was described in this paper. The NTHP protecting group is easily introduced by reaction of 2-chloro-THP with imidazole. Lithiation followed by reaction with an appropriate electrophile affords 2-halogeno N-THP derivatives. The THP protecting group is then cleaved to get the title compounds in good to high yields.

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Rault Sylvain, Primas Nicolas, Bouillon Alexandre, Lancelot Jean-Charles, Santos Sopkova-de Oliveira Jana and Lohier Jean-François, A New Methodology to Prepare 2-Halogenoimidazoles via a N-THP Protection, Letters in Organic Chemistry 2008; 5 (1) . https://dx.doi.org/10.2174/157017808783330252