Citation: Aidang Lu, Yunting Liu, Yanjun Jiang. Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds[J]. University Chemistry, ;2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029 shu

Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds

1.
School of Chemical Engineering, Hebei University of Technology, Tianjin 300130, China;
2.
National-Local Joint Engineering Laboratory for Energy Conservation in Chemical Process Integration and Resources Utilization, Tianjin 300130, China

Received Date: 8 January 2024
Revised Date: 4 March 2024

Triazolopyrimidine compounds containing carboxyl and thioether groups were synthesized using 3-amino-5-mercapto-1,2,4-triazole, benzyl bromide, and diethyl ethoxymethylenemalonate (EMME) as starting materials. The synthesis involved nucleophilic substitution, cyclization, and hydrolysis reactions. The resulting products were characterized and analyzed for their structures. The experiment included techniques such as heating reflux, TLC (thin-layer chromatography) detection, filtration, and recrystallization, which aimed to enhance students’ skills in multi-step organic compound synthesis and spectral analysis. Triazolopyrimidine compounds are widely found in natural products and pharmaceuticals. The synthesis of these compounds not only provides insight into societal demands but also integrates cutting-edge research and theoretical knowledge taught in the classroom, thereby improving the quality of experimental teaching and achieving excellent educational outcomes.
- Transformation of science and education,
- Comprehensive organic chemistry experiment,
- Triazolopyrimidine compounds,
- Organic synthesis
1. [1]
2. [2]
3. [3]
4. [4]
  Amin, A.; Qadir, T.; Sharma, P. K.; Jeelani, I.; Abe, H. Open Med. Chem. J. 2022, 16, e87410452209010.
5. [5]
  Feng, J.; Geng, W. C.; Jiang, H. F.; Wu, B. Biotechnol. Adv. 2022, 54, 107813.
6. [6]
  Jadhav, P. A.; Baravkar, A. Asian J. Pharm. Clin. Res. 2022, 15 (2), 4.
7. [7]
  Srivastava, A.; Singh, P. K.; Ali, A.; Singh, P. P.; Srivastava, V. RSC Adv. 2020, 10, 39495.
8. [8]
9. [9]
  Wang, T. N.; Yang, S.; Li, H. Y.; Lu, A. D.; Wang, Z. W.; Yao, Y. W.; Wang, Q. M. J. Agric. Food Chem. 2020, 68 (2), 471.
10. [10]
  Savateev, K. V.; Fedotov, V. V.; Rusinov, V. L.; Kotovskaya, S. K.; Spasov, A. A.; Kucheryavenko, A. F.; Vasiliev, P. M.; Kosolapov, V. A.; Sirotenko, V. S.; Gaidukova, K. A.; et al. Molecules 2022, 27 (1), 274.
11. [11]
  Abd El-Aleam, R. H.; George, R. F.; Hassan, G. S.; Abdel-Rahman, H. M. Bioorg. Chem. 2020, 94, 103411.
12. [12]
  Heras, M.; Font, D.; Linden, A.; Villalgordo, J. M. Helv. Chim. Acta 2003, 86, 3204.
13. [13]
1. [1]
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沈阳化工大学材料科学与工程学院沈阳 110142