Advances in the Modifications of 4-Monosubstituted 1,2,3-Triazoles

doi:10.6023/A23060284

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (11): 1577-1589.DOI: 10.6023/A23060284 Previous Articles Next Articles

Review

4-单取代-1,2,3-三氮唑的修饰转化研究进展

杨保民^a, 张水滔^a, 董鲜^b, 秦贵平^a^,^*(), 江玉波^a^,^*()

a 昆明理工大学理学院昆明 650500
b 云南中医药大学中药学院昆明 650500

投稿日期:2023-06-12 发布日期:2023-08-14

作者简介:

杨保民, 昆明理工大学高级工程师, 硕士生导师. 1984年进入昆明理工大学从事化学教学与实验室管理工作, 2004年筹建昆明理工大学基础有机化学实验中心, 为选择性催化与合成研究团队成员. 主要研究方向为化学分离与富集, 以第一作者或通讯作者身份发表学术论文10余篇.

秦贵平, 昆明理工大学副教授, 硕士生导师, 2018年博士毕业于中国科学院大学(中国科学院兰州化学物理研究所), 师从黄汉民教授, 同年进入昆明理工大学开展科研工作. 主要从事过渡金属催化的还原交叉偶联合成碳碳键、过渡金属催化的不对称反应以及季碳合成. 以第一作者或通讯作者身份在J. Am. Chem. Soc.、ACS Catal.、Org. Lett.、Org. Chem. Front.、ACS Sustainable Chem. Eng.等期刊发表学术论文10余篇.

江玉波, 昆明理工大学教授, 硕士生导师, 有机化学学科方向带头人, 选择性催化与合成研究团队负责人. 2011年博士毕业于同济大学, 师从匡春香教授和王剑波教授, 同年进入昆明理工大学开展工作, 曾先后访学于北京大学及牛津大学. 主要研究兴趣: (1)功能化1,2,3-三氮唑衍生物的合成及应用; (2)杂原子的配位性能及应用; (3)碳-氢键活化构建策略; (4)抗菌活性导向的产品结构设计、合成与应用. 以第一作者或通讯作者身份在Chem. Soc. Rev.、Org. Lett.、Org. Chem. Front.、Adv. Synth. Catal.、Org. Biomol. Chem.、《有机化学》及《化学进展》等期刊发表学术论文50余篇.

基金资助:
国家自然科学基金(21662020); 国家自然科学基金(21901091); 院士(专家)工作站项目云南省王源超专家工作站(202305AF150018)

Advances in the Modifications of 4-Monosubstituted 1,2,3-Triazoles

Baomin Yang^a, Shuitao Zhang^a, Xian Dong^b, Guiping Qin^a(), Yubo Jiang^a()

a Faculty of Science, Kunming University of Science and Technology, Kunming 650500
b College of Traditional Chinese Medicine, Yunnan University of Chinese Medicine, Kunming 650500

Received:2023-06-12 Published:2023-08-14
Contact: *E-mail: qin-guiping@kust.edu.cn; ybjiang@kust.edu.cn
Supported by:
National Natural Science Foundation of China(21662020); National Natural Science Foundation of China(21901091); Academician (Expert) Workstation Project, Wang Yuan Chao Expert Workstation in Yunnan Province(202305AF150018)

1,2,3-Triazole is a kind of 5-membered N-heterocycle widely applied in pharmaceutical, pesticide and materials. 1,2,3-Trizole chemistry has stepped into a new era in the fields of organic synthesis and pharmacochemistry since the Cu-catalyzed azide-alkyne dipolar cycloaddition was founded by the Sharpless and Meldal groups in 2002. 4-Monosubstituted 1,2,3-triazole is a noble member in its family owing to the structural merits of facile modifications, leading to novel molecules. The transformations of 4-monosubstituted 1,2,3-triazoles basing on different reaction sites including the N¹, N²and N³ are reviewed. The substrate scope, limitation, and representative mechanism are also discussed.

Key words: 4-monosubstitution, 1,2,3-triazole, modification, C—N coupling, ring-opening reaction

Cite this article

Baomin Yang, Shuitao Zhang, Xian Dong, Guiping Qin, Yubo Jiang. Advances in the Modifications of 4-Monosubstituted 1,2,3-Triazoles[J]. Acta Chimica Sinica, 2023, 81(11): 1577-1589.

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Fig. & Tab. 35

Figure 1. Biologically active 1,2,3-triazole derivatives

Scheme 1. N1 5-Quinolylation promoted by visible light without metal

Scheme 2. Coordination strategy-induced selective N1 5-quinolylation

Scheme 3. N1 2-Biphenylation

Scheme 4. N1 Allylation

Scheme 5. N1 Benzylation

Scheme 6. N1 and N2 benzylation

Scheme 7. Blue light promoted N1 alkylation

Scheme 8. Electrochemical N1 alkylation

Scheme 9. Diacyl peroxide participated N1 alkylation

Scheme 10. N1 Sulfonylation

Scheme 11. Pd-Catalyzed N2 arylation

Scheme 12. Highly N2-selective coupling of NH-1,2,3-triazoles with indole or pyrrole

Scheme 13. Diaryl iodonium salt participated N2 arylation

Scheme 14. N2 Coupling based on Mitsunobu reaction

Scheme 15. DABCO Mediated N2 Michael addition

Scheme 16. Au-Catalyzed N2 alkylation

Scheme 17. Amide participated N2 alkylation

Scheme 18. P2O5-Mediated synthesis of sulfur-containing 1,2,3-triazoles

Scheme 19. Remote C(sp3)—H participated N2 alkylation

Scheme 20. Selective N2 iodofunctionalization

Scheme 21. Selective N2 modification by aryldiazoacetates

Scheme 22. Allenamides participated N2 allylation

Scheme 23. Alkyne participated N2 vinylation

Scheme 24. Vinylboronic acids participated N2 vinylation

Scheme 25. N2 Propargylation

Scheme 26. N2 Allenylation

Scheme 27. N2 Sulfonylation

Scheme 28. N3 Alkylation

Scheme 29. Synthesis of 5-amino-1,2,3-triazolo[5,1-a]-isoquinolines

Scheme 30. Intramolecular reaction to isoquinoline fused 1,2,3-triazoles

Scheme 31. Cyclization of 4-o-aminoaryl-1,2,3-triazoles and 2-alkynyl- benzaldehydes

Scheme 32. Triflic anhydride promoted ring-opening reaction

Scheme 33. Acyl halides promoted ring-opening reaction

Scheme 34. Fluorinated anhydrides promoted ring-opening reaction

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4-单取代-1,2,3-三氮唑的修饰转化研究进展

Advances in the Modifications of 4-Monosubstituted 1,2,3-Triazoles

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