Izvestiya of Saratov University.

Chemistry. Biology. Ecology

ISSN 1816-9775 (Print)
ISSN 2541-8971 (Online)


For citation:

Lyapun D. V., Kruzhilin A. A., Shikhaliev K. S. Synthesis of 2-alkyl-5-phenyl-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol derivatives. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2024, vol. 24, iss. 2, pp. 129-134. DOI: 10.18500/1816-9775-2024-24-2-129-134, EDN: QVPMHA

This is an open access article distributed under the terms of Creative Commons Attribution 4.0 International License (CC-BY 4.0).
Full text:
(downloads: 91)
Language: 
Russian
Heading: 
Article type: 
Article
UDC: 
547.792+547.859+620.193
EDN: 
QVPMHA

Synthesis of 2-alkyl-5-phenyl-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol derivatives

Autors: 
Lyapun Denis V., Voronezh State University
Kruzhilin Alexey A., Voronezh State University
Shikhaliev Khidmet S., Voronezh State University
Abstract: 

The problem of acid corrosion of steel is of signifi cant importance, particularly in the context of the oil extraction industry, where acid treatment of wells and surrounding spaces is widely employed. This research article focuses on the synthesis and investigation of previously unstudied derivatives of the class of 2-alkyl-5-phenyl-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-ols – organic compounds potentially highly eff ective as inhibitors of acid corrosion of steel. The method for synthesizing the proposed compounds involves the condensation of 3-alkyl5-amino-1H-1,2,4-triazoles with cinnamaldehyde. The structure of the synthesized compounds has been confi rmed using 1H NMR and LCMS methods. The study has revealed that the developed synthesis conditions yield the target tetrahydrotriazolopyrimidinols with alkyl substituents containing up to three carbon atoms. However, an increase in the length of alkyl substituents intensifi es side reactions, making the isolation of the target compounds challenging. The obtained research results are signifi cant for the development of eff ective organic inhibitors of acid corrosion of steel of a new class. These fi ndings can serve as a basis for further research in this area, contributing to the development of new methods for corrosion prevention and improving the resistance of materials used in the oil industry. Thus, this study not only describes a new synthetic approach to obtaining inhibitors of corrosion in the tetrahydrotriazolopyrimidinol class but also holds prospective practical value in the fi eld of industrial technologies and materials science.

Reference: 
  1. Fredd C. N., Fogler H. S. Alternative stimulation fl uids and their impact on carbonate acidizing // SPE Journal. March 1998. Vol. 3, № 1. P. 34–41. https://doi.org/10.2118/31074-PA
  2. Barmatov E., Geddes J., Hughes T., Nagl M. Research on corrosion inhibitors for acid stimulation // NACE CORROSION. 2012. NACE-2012-1573.
  3. Авдеев Я. Г., Кузнецов Ю. И. Физико-химические аспекты ингибирования кислотной коррозии металлов ненасыщенными органическими соединениями // Успехи химии. 2012. Т. 81, № 12. С. 1133–1145. https://doi.org/10.1070/RC2012v081n12ABEH004292
  4. Kruzhilin A. A., Shevtsov D. S., Potapov A. Yu., Shikhaliev Kh. S., Kozaderov O. A., Prabhakar Ch., Kasatkin V. E. Novel inhibitory compositions based on 4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol derivatives for steel acid corrosion protection // Int. J. Corros. Scale Inhib. 2022. Vol. 11, № 2. P. 774–795. https://doi.org/10.17675/2305-6894-2022-11-2-22 
  5. Zemlyanaya N. I., Karnozhitskaya T. M., Musatov V. I., Konovalova I. S., Shishkina S. V., Lipson V. V. Synthesis and chemical transformations of 5-alkyl (phenyl)-4, 5, 6, 7-tetrahydro [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-oles // Russ. J. Org. Chem. 2018. Vol. 54. P. 1241–1249. https://doi.org/10.1134/S1070428018080201
  6. Lipson V. V., Karnozhitskaya T. M., Shishkina S. V., Shishkin O. V., Turov A. V. Reactions of 3-amino-1, 2, 4-triazoles with cinnamic aldehydes // Russ. Chem. Bull. 2009. Vol. 58. P. 1441–1444. https://doi.org/10.1007/s11172-009-0193-1
  7. Kruzhilin A. A., Lyapun D. V., Shevtsov D. S., Kozaderov O. A., Potapov A. Yu., Zartsyn I. D., Prabhakar Ch., Shikhaliev Kh. S. New [1, 2, 4] triazolo [1, 5-a] pyrimidine-7-one corrosion inhibitors for copper in chloride environments // Int. J. Corros. Scale Inhib. 2021. Vol. 10, № 4. P. 1474–1492. https://doi.org/10.17675/2305-6894-2021-10-4-7
  8. Десенко С. М., Орлов В. Д. Азагетероциклы на основе ароматических непредельных кетонов. Харьков : Фолио, 1998. 148 с.
Received: 
14.02.2024
Accepted: 
05.03.2024
Published: 
31.05.2024
Short text (in English):
(downloads: 56)