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Features of reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with binucleophiles

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Abstract

Regardless of pH and a solvent nature the reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with hydrazine led to the formation of pyrazole derivatives. The salts reacted with thiourea via intermediate formation of 4-arylpyrimidine-2-thiol to give (Z)-2-[(β-aroylvinyl)sulfanyl]-4-arylpyrimidines. In the case of N,N'-diphenylthiourea the reaction provided 6-aryl-3-aroyl-1-phenylpyridinium bromides. Pyridine hydrobromide liberated in the reaction course has a major influence on the process chemoselectivity.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Scientific-Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences, pr. Azatutyan 26, Yerevan, 0014, Armenia

    R. Dzh. Khachikyan, Z. G. Ovakimyan, G. A. Panosyan, R. A. Tamazyan & A. G. Ayvazyan

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  1. R. Dzh. Khachikyan
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  2. Z. G. Ovakimyan
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  3. G. A. Panosyan
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  4. R. A. Tamazyan
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  5. A. G. Ayvazyan
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Correspondence to R. Dzh. Khachikyan.

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Original Russian Text © R.Dzh. Khachikyan, Z.G. Ovakimyan, G.A. Panosyan, R.A. Tamazyan, A.G. Ayvazyan, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 7, pp. 1095–1101.

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Khachikyan, R.D., Ovakimyan, Z.G., Panosyan, G.A. et al. Features of reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with binucleophiles. Russ J Gen Chem 86, 1574–1580 (2016). https://doi.org/10.1134/S1070363216070070

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  • DOI: https://doi.org/10.1134/S1070363216070070

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