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Nucleophilic halogenation of imidazole N-oxides

Евгений И. Адиулин, Антон В. Кутасевич, Виталий С. Митянов, Иосиф И. Ткач, Татьяна Ю. Колдаева
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Abstract


A convenient method of accessing imidazole 2-halo derivatives is proposed, comprising O-acylation of imidazole N-oxide fluoroborate complexes with tosyl halogenides which further undergo cine-substitution of 3-tosyl group with a halogen anion. In conjunction with a previously proposed method of synthesizing N-oxides of 2-unsubstituted 1-arylimidazoles this method enables one to substantially expand the range of accessible compounds.

How to Cite
Adiulin, Y. I.; Kutasevich, A. V.; Mityanov, V. S.; Tkach, I. I.; Koldaeva, T. Yu. Chem. Heterocycl. Compd. 2015, 51, 500. [Khim. Geterotsikl. Soedin. 2015, 51, 500.]

For this article in the English edition see DOI 10.1007/s10593-015-1727-0

 


Keywords


haloimidazoles; imidazoles; imidazole N-oxides; tosyl bromide; tosyl chloride; nucleophilic cine-substitution

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