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Synthesis and dehydrogenation of spinaceamine and spinacine 4-hetaryl derivatives

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Abstract

The reaction of histamine and histidine with various hetarylaldehydes under the conditions of the base-catalyzed Pictet-Spengler process affords 4-hetaryl-substituted derivatives of spinaceamine and spinacine. The dehydrogenation of the 4-hetaryl-substituted spinaceamine derivatives using elemental sulfur in DMF at 120–130°C led to the formation of 4-hetaryl derivatives of imidazo[4,5-c]-pyridine. Under similar conditions the 4-hetaryl-substituted spinacine derivatives suffered both the dehydrogenation and oxidative decarboxylation resulting in the products identical to the compounds obtained by the dehydrogenation of 4-hetaryl-substituted spinaceamine.

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Authors and Affiliations

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

    N. N. Smolyar, M. G. Abramyants, T. I. Zavyazkina, D. I. Matveeva, Ya. S. Borodkin & I. A. Voloskii

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  1. N. N. Smolyar
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  2. M. G. Abramyants
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  3. T. I. Zavyazkina
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  4. D. I. Matveeva
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  5. Ya. S. Borodkin
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  6. I. A. Voloskii
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Correspondence to N. N. Smolyar.

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Original Russian Text © N.N. Smolyar, M.G. Abramyants, T.I. Zavyazkina, D.I. Matveeva, Ya.S. Borodkin, I.A. Voloskii, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 8, pp. 1228–1231.

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Smolyar, N.N., Abramyants, M.G., Zavyazkina, T.I. et al. Synthesis and dehydrogenation of spinaceamine and spinacine 4-hetaryl derivatives. Russ J Org Chem 45, 1219–1223 (2009). https://doi.org/10.1134/S1070428009080181

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  • DOI: https://doi.org/10.1134/S1070428009080181

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