Effect of substituent in pyridine-2-carbaldehydes on their heterocyclization to 1,2,4-triazines and 1,2,4-triazine 4-oxides
- Authors: Krinochkin A.P.1, Kopchuk D.S.1,2, Chepchugov N.V.1, Kovalev I.S.1, Zyryanov G.V.1,2, Rusinov V.L.1,2, Chupakhin O.N.1,2
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Affiliations:
- Yeltsin Ural Federal University
- Postovskii Institute of Organic Synthesis, Ural Branch
- Issue: Vol 53, No 7 (2017)
- Pages: 963-970
- Section: Article
- URL: https://bakhtiniada.ru/1070-4280/article/view/216495
- DOI: https://doi.org/10.1134/S1070428017070016
- ID: 216495
Cite item
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.
About the authors
A. P. Krinochkin
Yeltsin Ural Federal University
Email: gvzyryanov@gmail.com
Russian Federation, ul. Mira 19, Yekaterinburg, 620002
D. S. Kopchuk
Yeltsin Ural Federal University; Postovskii Institute of Organic Synthesis, Ural Branch
Email: gvzyryanov@gmail.com
Russian Federation, ul. Mira 19, Yekaterinburg, 620002; ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990
N. V. Chepchugov
Yeltsin Ural Federal University
Email: gvzyryanov@gmail.com
Russian Federation, ul. Mira 19, Yekaterinburg, 620002
I. S. Kovalev
Yeltsin Ural Federal University
Email: gvzyryanov@gmail.com
Russian Federation, ul. Mira 19, Yekaterinburg, 620002
G. V. Zyryanov
Yeltsin Ural Federal University; Postovskii Institute of Organic Synthesis, Ural Branch
Author for correspondence.
Email: gvzyryanov@gmail.com
Russian Federation, ul. Mira 19, Yekaterinburg, 620002; ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990
V. L. Rusinov
Yeltsin Ural Federal University; Postovskii Institute of Organic Synthesis, Ural Branch
Email: gvzyryanov@gmail.com
Russian Federation, ul. Mira 19, Yekaterinburg, 620002; ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990
O. N. Chupakhin
Yeltsin Ural Federal University; Postovskii Institute of Organic Synthesis, Ural Branch
Email: gvzyryanov@gmail.com
Russian Federation, ul. Mira 19, Yekaterinburg, 620002; ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990
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