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.

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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