INTERACTION OF 2-AMINO-(4-ARYL)-SUBSTITUTED THIA- AND OXAZOLES WITH 5-CYANO-1,2,4-TRIAZINES

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Abstract

An interaction of 6-aryl-1,2,4-triazine-5-carbonitriles with 2‑amino-substituted thiazoles and oxazoles has been studied. The difference in the reactivity of these aminoheterocycles depending on the presence of an oxygen or sulfur atom in their composition has been demonstrated. Previously, the 4-aryl-3-hydroxy-2,2'-bipyridines were obtained as products of aza-Diels–Alder reaction between 6-aryl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitriles and 2-amino-4-aryloxazoles. In the present work we have shown that the reaction of 6-aryl-1,2,4-triazine-5-carbonitriles with 2-aminothiazoles led to the products of ipso-substitution of cyano-group. The aza-Diels–Alder reaction of these compounds with 2,5-norbornadiene allowed to obtain (2,2'-bi)pyridines with the thiazol-2-amine moiety at alpha-position.

About the authors

A. P. Krinochkin

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

A. I. Matern

Ural Federal University

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg

G. V. Zyryanov

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

O. S. Taniya

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

E. R. Sharafieva

Ural Federal University; Ural State Medical University, Ministry of Healthcare of the Russian Federation

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620028, Yekaterinburg

E. D. Ladin

Ural Federal University

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg

D. S. Kopchuk

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

Ya. K. Shtaitz

Ural Federal University

Author for correspondence.
Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg

A. Rammohan

Ural Federal University

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg

O. N. Chupakhin

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

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Copyright (c) 2023 А.П. Криночкин, А. Раммохан, Я.К. Штайц, Д.С. Копчук, Е.Д. Ладин, Э.Р. Шарафиева, О.С. Тания, Г.В. Зырянов, А.И. Матерн, О.Н. Чупахин