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Synthesis of 2,3-Dihydro-1H-imidazo[1,2-a]pyridinium Systems by Halocyclization of 1-Alkenyl(propargyl)-2-aminopyridinium Halides

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Abstract

Reaction of 2-aminopyridine with allyl bromide, methallyl chloride, 2-bromoallyl bromide, and propargyl bromide in acetone furnished 2-amino-1-allyl-, methallyl-, (2-bromoallyl)-, and propargylpyridinium halides. 2-Amino-1-allyl(methallyl)pyridinium halides reacted with bromine and iodine to form 2-halomethyl-2,3-dihydro-1H-imidazo[1,2-a]pyridinium systems. 2-Amino-1-(2-bromoallyl)pyridinium bromide underwent heterocyclization under the action of bromine, and did not react with iodine. 2-Amino-1-propargylpyridinium bromide reacted with bromine and iodine to form 2-halomemylene-2,3-dihydro-1H-imidazo[1,2-a]pyridinium systems.

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Funding

This work was financially supported by the Government of the Russian Federation (Decree no. 211 of March 16, 2013, agreement no. 02.A03.21.0011) and the Ministry of Education and Science of the Russian Federation (project no. 4.9665.2017/8.9).

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Authors and Affiliations

  1. South Ural State University (National Research University), pr. Lenina 76, Chelyabinsk, 454080, Russia

    E. V. Kalita, D. G. Kim, D. A. Rakhmatullina, M. A. Pylneva & E. M. Krynina

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  1. E. V. Kalita
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  2. D. G. Kim
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  3. D. A. Rakhmatullina
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  4. M. A. Pylneva
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  5. E. M. Krynina
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Correspondence to E. V. Kalita.

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No conflict of interest was declared by the authors.

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 8, pp. 1176–1181.

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Kalita, E.V., Kim, D.G., Rakhmatullina, D.A. et al. Synthesis of 2,3-Dihydro-1H-imidazo[1,2-a]pyridinium Systems by Halocyclization of 1-Alkenyl(propargyl)-2-aminopyridinium Halides. Russ J Gen Chem 89, 1570–1574 (2019). https://doi.org/10.1134/S107036321908005X

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