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Halogenation of 2-Unsubstituted and 2-Methylimidazo[4,5-b]pyridine Derivatives

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Abstract

Halogenation of 2-unsubstituted and 2-methylimidazo[4,5-b]pyridines and their N-methyl derivatives with bromine and chlorine in acetic acid takes different pathways, depending on the acetic acid concentration. The bromination in 50% aqueous acetic acid gives only 6-bromoimidazo[4,5-b]pyridines; bromination and chlorination of 2-unsubstituted imidazo[4,5-b]pyridines in glacial acetic acid leads to 5,6-dibromo(dichloro)imidazo[4,5-b]pyridin-2-ones, and bromination of 2-methylimidazo[4,5-b]pyridines in glacial acetic acid involves both the pyridine ring and the 2-methyl group to afford the corresponding 6-bromo-2-tribromomethylimidazo[4,5-b]pyridines.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, ul. R. Lyuksemburg 70, Donetsk, 83114, Ukraine

    Yu. M. Yutilov, Kh. Ya. Lopatinskaya, N. N. Smolyar & S. V. Gres’ko

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  1. Yu. M. Yutilov
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  2. Kh. Ya. Lopatinskaya
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  3. N. N. Smolyar
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  4. S. V. Gres’ko
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 3, 2005, pp. 457–461.

Original Russian Text Copyright © 2005 by Yutilov, Lopatinskaya, Smolyar, Gres’ko.

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Yutilov, Y.M., Lopatinskaya, K.Y., Smolyar, N.N. et al. Halogenation of 2-Unsubstituted and 2-Methylimidazo[4,5-b]pyridine Derivatives. Russ J Org Chem 41, 450–454 (2005). https://doi.org/10.1007/s11178-005-0186-y

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  • DOI: https://doi.org/10.1007/s11178-005-0186-y

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