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Synthesis of 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids

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Abstract

Nitration of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one gave its 5-nitro derivative which was subjected to alkylation with dimethyl sulfate, diethyl sulfate, and benzyl(dimethyl)phenylammonium chloride. The resulting 1,3-dimethyl-, 1,3-diethyl-, and 1,3-dibenzyl-5-nitro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones were reduced to the corresponding 1,3-dialkyl-5-amino-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, and the latter reacted with itaconic acid to produce 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids. 1-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acid was obtained by analogous reaction with 5-amino-2,3-dihydro-1H-imidazo[4,5-b]-pyridin-2-one.

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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

    N. N. Smolyar, N. N. Troyan, A. B. Vasilechko, D. A. Lomov & Yu. M. Yutilov

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  1. N. N. Smolyar
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  2. N. N. Troyan
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  3. A. B. Vasilechko
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  4. D. A. Lomov
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  5. Yu. M. Yutilov
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Correspondence to N. N. Smolyar.

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Original Russian Text © N.N. Smolyar, N.N. Troyan, A.B. Vasilechko, D.A. Lomov, Yu.M. Yutilov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1706–1708.

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Smolyar, N.N., Troyan, N.N., Vasilechko, A.B. et al. Synthesis of 1-(1,3-dialkyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl)-5-oxopyrrolidine-3-carboxylic acids. Russ J Org Chem 43, 1706–1709 (2007). https://doi.org/10.1134/S1070428007110206

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  • DOI: https://doi.org/10.1134/S1070428007110206

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