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Dehydrogenation of 4-aryl(hetaryl) spinacine derivatives with dimethyl sulfoxide

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Abstract

Aromatization of 4-aryl(hetaryl)tetrahydroimidazo[4,5-c]pyridine-6-carboxylic acids and their lithium salts by the action of dimethyl sulfoxide has been revealed for the first time. Heating of these compounds in DMSO for 5–7 h at 90–95°C leads to the formation of 4-aryl(hetaryl)imidazo[4,5-c]pyridine derivatives as a result of dehydrogenation and decarboxylation. Heating of the corresponding lithium salts generated in situ (DMSO, 90–95°C, 3–5 h) affords difficultly accessible 4-aryl(hetaryl)imidazo[4,5-c]pyridine-6-carboxylic acids.

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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

    D. A. Lomov, M. G. Abramyants, N. V. Astashkina, N. I. Korotkikh & S. V. Gres’ko

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  1. D. A. Lomov
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  2. M. G. Abramyants
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  3. N. V. Astashkina
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  4. N. I. Korotkikh
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  5. S. V. Gres’ko
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Correspondence to M. G. Abramyants.

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Original Russian Text © D.A. Lomov, M.G. Abramyants, N.V. Astashkina, N.I. Korotkikh, S.V. Gres’ko, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 7, pp. 1055–1058.

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Lomov, D.A., Abramyants, M.G., Astashkina, N.V. et al. Dehydrogenation of 4-aryl(hetaryl) spinacine derivatives with dimethyl sulfoxide. Russ J Org Chem 50, 1039–1042 (2014). https://doi.org/10.1134/S1070428014070185

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  • DOI: https://doi.org/10.1134/S1070428014070185

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