Synthesis of a series of novel dihydro-[1,2,4]triazolo [1,5-a]pyrimidine scaffolds: Dual solvent-catalyst activity of a low viscous and acid-functionalized ionic liquid

References

• Tanaka, K.; Toda, F. Solvent-Free Organic Synthesis. Chem. Rev. 2000, 100, 1025–1074. DOI: 10.1021/cr940089p.
   PubMed Web of Science ®Google Scholar
• Wenda, S.; Illner, S.; Mell, A.; Kragl, U. Industrial Biotechnology—the Future of. Green Chem. 2011, 13, 3007–3047. DOI: 10.1039/c1gc15579b.
   Web of Science ®Google Scholar
• Khaligh, N. G.; Teng, L. S.; Ling, O. C.; Johan, M. R.; Ching, J. J. 4-Imidazol-1-yl-Butane-1-Sulfonic Acid or a Novel Liquid Salt? The NMR Analysis and Dual Solvent-Catalytic Efficiency for One-Pot Synthesis of Xanthenes. J. Mol. Liq. 2019, 278, 19–32. DOI: 10.1016/j.molliq.2019.01.041.
   Web of Science ®Google Scholar
• Mihankhah, T.; Johan, M. R.; Ching, J. J.; Khaligh, N. G. 4-Imidazol-1-yl-Butane-1-Sulfonic Acid Ionic Liquid: Synthesis, Structural Analysis, Physical Properties and Catalytic Application as Dual Solvent-Catalyst. Phosphorus, Sulfur, Silicon Rel. Elem. 2019, 194, 866–878. DOI: 10.1080/10426507.2018.1487426.
   Web of Science ®Google Scholar
• Khaligh, N. G.; Chong, K. F.; Mihankhah, T.; Titinchi, S.; Johan, M. R.; Ching, J. J. An Efficient Synthesis of Pyrrolidinone Derivatives in the Presence of 1,1’-Butylenebis(3-Sulfo-3H-Imidazol-1-Ium) Chloride. Aust. J. Chem. 2018, 71, 566–572. DOI: 10.1071/CH18246.
   Web of Science ®Google Scholar
• Khaligh, N. G.; Mihankhah, T.; Johan, M. R. Green One-Pot Multicomponent Synthesis of Pyrrolidinones Using Planetary Ball Milling Process under Solventfree Conditions. Synth. Commun. 2019, 49, 1334–1342. DOI: 10.1080/00397911.2019.1601225.
   Web of Science ®Google Scholar
• Oukoloff, K.; Lucero, B.; Francisco, K. R.; Brunden, K. R.; Ballatore, C. 1,2,4-Triazolo[1,5-a]Pyrimidines in Drug Design. Eur. J. Med. Chem. 2019, 165, 332–346. DOI: 10.1016/j.ejmech.2019.01.027.
   PubMed Web of Science ®Google Scholar
• Zhang, N.; Kaloustian, S. A.; Nguyen, T.; Afragola, J.; Hernandez, R.; Lucas, J.; Gibbons, J.; Beyer, C. Synthesis and SAR of [1,2,4]Triazolo[1,5-a]Pyrimidines, a Class of Anticancer Agents with a Unique Mechanism of Tubulin Inhibition. J. Med. Chem. 2007, 50, 319–327. DOI: 10.1021/jm060717i.
   PubMed Web of Science ®Google Scholar
• Esteban-Parra, G. M.; Méndez-Arriaga, J. M.; Rodríguez-Diéguez, A.; Quirós, M.; Salas, J. M.; Sánchez-Moreno, M. High Antiparasitic Activity of Silver Complexes of 5,7-Dimethyl-1,2,4-Triazolo[1,5-a]Pyrimidine. J. Inorg. Biochem. 2019, 201, 110810. DOI: 10.1016/j.jinorgbio.2019.110810.
   PubMed Web of Science ®Google Scholar
• Abd El-Aleam, R. H.; George, R. F.; Hassan, G. S.; Abdel-Rahman, H. M. Synthesis of 1,2,4-Triazolo[1,5-a]Pyrimidine Derivatives: Antimicrobial Activity, DNA Gyrase Inhibition and Molecular Docking. Bioorg. Chem. 2020, 94, 103411. DOI: 10.1016/j.bioorg.2019.103411.
   PubMed Web of Science ®Google Scholar
• Mostafa, Y. A. H.; Hussein, M. A.; Radwan, A. A.; Kfafy, A. E. N. Synthesis and Antimicrobial Activity of Certain New 1,2,4-Triazolo[1,5-a]Pyrimidine Derivatives. Arch. Pharm. Res. 2008, 31, 279–293. DOI: 10.1007/s12272-001-1153-1.
   PubMed Web of Science ®Google Scholar
• Wang, H.; Lee, M.; Peng, Z.; Blazquez, B.; Lastochkin, E.; Kumarasiri, M.; Bouley, R.; Chang, M.; Mobashery, S. Synthesis and Evaluation of 1,2,4-Triazolo[1,5-a]Pyrimidines as Antibacterial Agents against Enterococcus faecium. J. Med. Chem. 2015, 58, 4194–4203. DOI: 10.1021/jm501831g.
   PubMed Web of Science ®Google Scholar
• Yang, F.; Yu, L. Z.; Diao, P. C.; Jian, X. E.; Zhou, M. F.; Jiang, C. S.; You, W. W.; Ma, W. F.; Zhao, P. L. Novel [1,2,4]Triazolo[1,5-a]Pyrimidine Derivatives as Potent Antitubulin Agents: Design, Multicomponent Synthesis and Antiproliferative Activities. Bioorg. Chem. 2019, 92, 103260. DOI: 10.1016/j.bioorg.2019.103260.
   PubMed Web of Science ®Google Scholar
• Huang, B.; Li, C.; Chen, W.; Liu, T.; Yu, M.; Fu, L.; Sun, Y.; Liu, H.; Clercq, E. D.; Pannecouque, C.; et al. Fused Heterocycles Bearing Bridgehead Nitrogen as Potent HIV-1 NNRTIs. Part 3: Optimization of [1,2,4]Triazolo[1,5-a]Pyrimidine Core via Structure-Based and Physicochemical Property-Driven Approaches. Eur. J. Med. Chem. 2015, 92, 754–765. DOI: 10.1016/j.ejmech.2015.01.042.
   PubMed Web of Science ®Google Scholar
• Chen, Q.; Zhu, X. L.; Jiang, L. L.; Ming, Z.; Guang, L.; Yang, F. Synthesis, Antifungal Activity and CoMFA Analysis of Novel 1,2,4-Triazolo[1,5-a]Pyrimidine Derivatives. Eur. J. Med. Chem. 2008, 43, 595–603. DOI: 10.1016/j.ejmech.2007.04.021.
   PubMed Web of Science ®Google Scholar
• Fischer, G. Recent Progress in 1,2,4-Triazolo[1,5-a]Pyrimidine Chemistry. In Advances in Heterocyclic Chemistry; Katritzky A. R., Ed.; Academic Press: Waltham, MA, 2007; pp 143–219.
   Google Scholar
• Fizer, M.; Slivka, M. Synthesis of [1,2,4]Triazolo[1,5-a]Pyrimidine (Microreview). Chem. Heterocycl. Comp. 2016, 52, 155–157. DOI: 10.1007/s10593-016-1851-5.
   Web of Science ®Google Scholar
• Khaligh, N. G.; Mihankhah, T.; Johan, M. R. Synthesis of New Low-Viscous Sulfonic Acid-Functionalized Ionic Liquid and Its Application as a Brönsted Liquid Acid Catalyst for the One-Pot Mechanosynthesis of 4H-Pyrans through the Ball Milling Process. J. Mol. Liq. 2019, 277, 794–804. DOI: 10.1016/j.molliq.2019.01.024.
   Web of Science ®Google Scholar