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Reaction of 1,2,4-Triazine-5-carbonitriles with 5-[(2-Hydroxyethyl)sulfanyl]- and 5-{[2-(2-Hydroxyethoxy)-ethyl]sulfanyl}-3-amino-1,2,4-triazoles1

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Abstract

The solvent-free reaction of 1,2,4-triazine-5-carbonitriles with newly synthesized 5-[(2-hydroxyethyl)sulfanyl]- and 5-{[2-(2-hydroxyethoxy)ethyl]sulfanyl}-3-amino-1,2,4-triazoles under heating was studied. It was shown that in the case when the C5 atom of the 1,2,4-triazole ring bears hydroxy(ethoxy)ethylsulfanyl substituents, 5-amino-1,2,4-triazines are formed as the main reaction products, while the ipso-substitution products of the C5-cyano group of the substituted 1,2,4-triazole ring were isolated only as by-products. With a 1,2,4-triazole with a monoethylene glycol fragment at the C5 position, a complex mixture of products was formed.

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ACKNOWLEDGMENTS

The work was carried out using the equipment of the “Spectroscopy and Analysis of Organic Compounds” Center for Collective Use.

Funding

The work was financially supported by the Russian Science Foundation (project no. 20-13-00142-P, https://rscf.ru/project/20-13-00142/, synthesis of the final products) and Grant Council under the President of the Russian Federation (grant no. MD-167.2021.1.3, synthesis of the starting aminotriazoles).

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Correspondence to G. V. Zyryanov.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1501–1506 https://doi.org/10.31857/S0514749223100137.

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The paper is dedicated to the 125th anniversary of Academician I.Ya. Postovskii.

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Krinochkin, A.P., Ladin, E.D., Shtaitz, Y.K. et al. Reaction of 1,2,4-Triazine-5-carbonitriles with 5-[(2-Hydroxyethyl)sulfanyl]- and 5-{[2-(2-Hydroxyethoxy)-ethyl]sulfanyl}-3-amino-1,2,4-triazoles1. Russ J Org Chem 59, 1998–2002 (2023). https://doi.org/10.1134/S1070428023110210

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