Abstract
Derivatives of 1,2,4-triazole exhibit antimicrobial, anticonvulsant, anti-inflammatory, immunomodulatory, and other types of activity, which makes it possible to create effective drugs on their basis. Understanding the reaction mechanism for the formation of triazoles helps to control the chemical process and conduct targeted synthesis. Quantum-chemical modeling of the mechanism of interaction of diformylhydrazine with o- and p-aminophenols was carried out using the combined approach CCSD (T)/6–31+G*//B3LYP/6–311++G**. The elementary stages of the reaction, possible intermediate compounds, and transition states have been established. The obtained results have been compared with the data from NMR spectroscopy.
Similar content being viewed by others
Data availability
The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.
References
Chirkina EA, Krivdin LB, Nikonova BC, Grabel′nyh VA, Korchevin NA, Rosentsveig IB (2021) Quantum-chemical study of the mechanisms of organic reactions: X. On the interaction of potassium 1,3-propanedithiolate with 1,3-dichloropropene in the system hydrazine hydrate-KOH. Russ. J Org Chem (Engl Transl) 57:1073–1083. https://doi.org/10.31857/S0514749221070077
Richards D, Coleman J, Reynolds J, Aronson J (2011) Oxford handbook of practical drug therapy. Oxford University Press, Oxford, New York. https://doi.org/10.1093/med/9780199562855.001.0001
Maddila S, Pagadala R, Jonnalagadda SB (2013) 1,2,4-triazoles: a review of synthetic approaches and the biological activity. Lett Org Chem 10:693–714. https://doi.org/10.2174/157017861010131126115448
Gao F, Wang T, Xiao J, Huang G (2019) Antibacterial activity study of 1,2,4-triazole derivatives. Eur J Med Chem 173:274–281. https://doi.org/10.1016/j.ejmech.2019.04.043
Gomaa HAM, Sherief HAM, Hussein S, Gouda AM, Salem OIA, Alharbi KS, Hayallah AM, Youssif BGM (2020) Novel 1,2,4-triazole derivatives as apoptotic inducers targeting p53: synthesis and antiproliferative activity. Bioorganic Chem 105:104369–104375. https://doi.org/10.1016/j.bioorg.2020.104369
Aggarwal G, Sumran R (2020) An insight on medicinal attributes of 1,2,4-triazoles. Eur J Med Chem 205:112652. https://doi.org/10.1016/j.ejmech.2020.112652
Kumari M, Tahlan S, Narasimhan B, Ramasamy K, Lim SM, Shan SAA, Mani V, Kakkar S (2021) Synthesis and biological evaluation of heterocyclic 1,2,4-triazole scaffolds as promising pharmacological agents. BMC Chemistry 15:5. https://doi.org/10.1186/s13065-020-00717-y
Elokhina VN, Nakhmanovich AS, Yaroshenko TI, Stepanova ZV, Larina LI (2006) Synthesis of 4-(Hydroxyphenyl)-1,2,4-triazoles. Russ J Gen Chem 76:161–163. https://doi.org/10.1134/S1070363206010312
Larina LI, Lopyrev VA (2009) Nitroazoles: synthesis, structure and application. Springer, New York, 446 p. ISBN 978–0–387–98069–0 https://doi.org/10.1007/978-0-387-98070-6
Jin R, Wang Y, Guo H, Long X, Li J, Yue S, Zhang S, Zhang G, Meng Q, Wang C, Yan H, Tang Y, Zhou S (2020) Design, synthesis, biological activity, crystal structure and theoretical calculations of novel 1,2,4-triazole derivatives. J Mol Struct 1202:127234. https://doi.org/10.1016/j.molstruc.2019.127234
Demirbaş Ü, Özçifçi Z, Akçay HT, Menteşe E (2020) Novel phthalocyanines bearing 1,2,4 triazole substituents: synthesis, characterization, photophysical and photochemical properties. Polyhedron 181:114470. https://doi.org/10.1016/j.poly.2020.114470
Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB (2020) A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules 25:1909. https://doi.org/10.3390/molecules25081909
Wu J, Jiang Y, Lian Z, Li H, Zhang J (2021) Computational design and screening of promising energetic materials: the coplanar family of novel heterocycle-based explosives. Int J Quantum Chem 121:e26788. https://doi.org/10.1002/qua.26788
Gonnet L, Baron M, Baltas M (2021) Synthesis of biologically relevant 1,2,3- and 1,3,4-triazoles: from classical pathway to green chemistry. Molecules 26:5667–5675. https://doi.org/10.3390/molecules26185667
Aromí G, Barrios LA, Roubeau O, Gamez P (2011) Triazoles and tetrazoles: prime ligands to generate remarkable coordination materials. Coord Chem Review 255:485–546. https://doi.org/10.1016/j.ccr.2010.10.038
Mogensen SB, Taylor MK, Lee J-W (2020) Homocoupling reactions of azoles and their application in coordination chemistry. Molecules 25:5950–5956. https://doi.org/10.3390/molecules25245950
Neumann S, Biewend M, Rana S, Binder WH (2020) The CuAAC: principles, homogeneous and heterogeneous catalysts, and novel developments and applications. Macromol Rapid Commun 41:1900359. https://doi.org/10.1002/marc.201900359
Larina LI (2017) Tautomerism and structure of azoles: nuclear magnetic resonance spectroscopy. Adv Heterocyc Chem 124:233–321. https://doi.org/10.1016/bs.aihch.2017.06.003
Patel VM, Patel NB, Chan-Bacab MJ, Rivera G (2018) Synthesis, biological evaluation and molecular dynamics studies of 1,2,4-triazole clubbed Mannich bases. Comput Biol Chem 76:264–274. https://doi.org/10.1016/j.compbiolchem.2018.07.020
Karczmarzyk Z, Swatko-Ossor M, Wysocki W, Drozd M, Ginalska G, Pachuta-Stec A, Pitucha M (2020) New application of 1,2,4-triazole derivatives as antitubercular agents. Structure, In Vitro Screening and Docking Studies. Molecules 25:6033. https://doi.org/10.3390/molecules25246033
Larina LI (2021) Organosilicon azoles: structure, silylotropy and NMR spectroscopy. Adv Heterocycl Chem 133:1–63. https://doi.org/10.1016/bs.aihch.2019.08.001
Gaussian 09, Revision C.01 (2009) Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian Inc Wallingford CT
Berne BJ, Tuckerman M, Martyna G (1991) Molecular dynamics algorithm for multiple time scales: systems with long-range forces. J Chem Phys 94:6811. https://doi.org/10.1063/1.460259
González C, Schlegel HB (1990) Reaction path following in mass-weighted internal coordinates. J Phys Chem 94:5523–5527. https://doi.org/10.1021/j100377a021
González C, Schlegel HB (1991) Improved algorithms for reaction path following: higher-order implicit algorithms. J Chem Phys 95:5853–5860. https://doi.org/10.1063/1.461606
Chirkina EA, Larina LI, Komarova TN (2020) Quantum-chemical study of organic reaction mechanisms. IX. The interaction of benzoylacetylene with dithio- and diselenomalonamides. J Organometal Chem 915:1–6. https://doi.org/10.1016/j.jorganchem.2020.121242
Acknowledgements
Optimization of geometric parameters and calculation of molecular energy were performed by the CCSD(T)/6-31+G*//B3LYP/6-311++G** methods using the GAUSSIAN 09 program [22] at A.E. Favorsky Irkutsk Institute of Chemistry SB RAS on the computing cluster of the Baikal Analytical Center for Collective Use of the SB RAS (http://ckp-rf.ru/ckp/3050/). Experimental NMR results were also obtained with use of the equipment of the Baikal Analytical Centre for Collective Use of the SB RAS.
Author information
Authors and Affiliations
Contributions
All authors contributed to the study conception and design. Material preparation, data collection, and analysis were performed by Chirkina Elena and Larina Lyudmila. The first draft of the manuscript was written by Chirkina Elena and Larina Lyudmila commented on previous versions of the manuscript. All authors read and approved the final manuscript.
Corresponding author
Ethics declarations
Competing interests
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Previous publication: X see [1].
Supplementary information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Chirkina, E., Larina, L. Quantum-chemical study of organic reaction mechanisms. XI.*1 Biologically active 4-substituted 1,2,4-triazoles from diformylhydrazine and aminophenols. Struct Chem 33, 2023–2032 (2022). https://doi.org/10.1007/s11224-022-01969-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-022-01969-1