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Effect of substituent in pyridine-2-carbaldehydes on their heterocyclization to 1,2,4-triazines and 1,2,4-triazine 4-oxides

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Abstract

A series of substituted pyridine-2-carbaldehydes were brought into heterocyclization with isonitrosoacetophenone hydrazones, followed by aromatization by the action of oxidants or by dehydration in boiling acetic acid. As a result, substituted 3-(pyridin-2-yl)-1,2,4-triazines or 3-(pyridin-2-yl)-1,2,4-triazine 4-oxides were formed. 6-Formylpyridine-2-carbonitrile failed to undergo heterocyclization, 6-methylpyridine-2-carbaldehyde and methyl 6-formylpyridine-3-carboxylate can be converted to both 1,2,4-triazine and 1,2,4-triazine 4-oxide derivative, and only 1,2,4-triazine 4 oxides were obtained from 6-bromopyridine-2-carbaldehyde and 6-formyl-3-phenylpyridine-2-carbonitrile. Convenient procedures were proposed for the synthesis of some initial pyridinecarbaldehydes.

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Authors and Affiliations

  1. Yeltsin Ural Federal University, ul. Mira 19, Yekaterinburg, 620002, Russia

    A. P. Krinochkin, D. S. Kopchuk, N. V. Chepchugov, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov & O. N. Chupakhin

  2. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990, Russia

    D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov & O. N. Chupakhin

Authors
  1. A. P. Krinochkin
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  2. D. S. Kopchuk
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  3. N. V. Chepchugov
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  4. I. S. Kovalev
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  5. G. V. Zyryanov
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  6. V. L. Rusinov
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  7. O. N. Chupakhin
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Corresponding author

Correspondence to G. V. Zyryanov.

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Original Russian Text © A.P. Krinochkin, D.S. Kopchuk, N.V. Chepchugov, I.S. Kovalev, G.V. Zyryanov, V.L. Rusinov, O.N. Chupakhin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 7, pp. 951–958.

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Krinochkin, A.P., Kopchuk, D.S., Chepchugov, N.V. et al. Effect of substituent in pyridine-2-carbaldehydes on their heterocyclization to 1,2,4-triazines and 1,2,4-triazine 4-oxides. Russ J Org Chem 53, 963–970 (2017). https://doi.org/10.1134/S1070428017070016

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  • DOI: https://doi.org/10.1134/S1070428017070016

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