FeCl3-Mediated Assembly of heterocyclic compounds containing both pyrazole scaffolds and tertiary alcohol ester moieties

doi:10.6023/cjoc202601022

Chinese Journal of Organic Chemistry

ARTICLE

FeCl₃催化的含吡唑骨架与叔醇酯基杂环化合物的构建

谢速, 赵志飞^*, 李师伍^*

石河子大学化学化工学院/化工绿色过程省部共建国家重点实验室培育基地新疆石河子 832000

收稿日期:2026-01-16 修回日期:2026-02-25

FeCl₃-Mediated Assembly of heterocyclic compounds containing both pyrazole scaffolds and tertiary alcohol ester moieties

Xie Su, Zhao Zhifei^*, Li Shi-Wu^*

School of Chemistry and Chemical Engineering, Shihezi University/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering Shihezi, Xinjiang 832000

Received:2026-01-16 Revised:2026-02-25
Contact: ^*E-mail: lishiwu@shzu.edu.cn, zhaozf@shzu.edu.cn
Supported by:
Science and Technology Program of XPCC (No. 2023CB008-19), National Natural Science Foundation of China (No. 22461036 and No. 22101188).

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Abstract

Herein, we report a green synthetic method for the construction of heterocyclic compounds bearing a pyrazole core and a tertiary alcohol ester moiety, catalyzed by inexpensive and readily available FeCl₃. This method features a broad substrate scope, high functional group tolerance, and operational simplicity, with yields ranging from 82% to 98%. Furthermore, the practicality of this protocol is highlighted by scale-up experiments and synthetic transformations of the products, including the modification of marketed drugs.

Key words: Pyrazole scaffold, FeCl₃ catalysis, Heterocyclic compounds, Tertiary alcohol, Bioactive heterocycles

Cite this article

Xie Su, Zhao Zhifei, Li Shi-Wu. FeCl₃-Mediated Assembly of heterocyclic compounds containing both pyrazole scaffolds and tertiary alcohol ester moieties[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202601022.

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[1] For selected recent reviews on pyrazolones, see: (a) Hamama, W. S.; El-Gohary, H. G.; Kuhnert, N.; Zoorob, H. H. Curr. Org. Chem. 2012, 16, 373-399.(b) Sondhi, S. M.; Dinodia, M.; Singh, J.; Rani, R. Curr. Bioact. Comp. 2007, 3, 91-108.
[2] Shiohara H.; Fujikura H.; Fushimi N.; Ito F.; Isaji M. PCT Int. Appl.WO 2002098893, 2002; Chem. Abstr. 2003, 138, 24917.
[3] US 4529735, 1985; Washington, DC: U.S. Patent and Trademark Office.
[4] Zhao L.; Xiong F.-J.; Chen W.-X.; Chen F.-E.Synthesis. 2011, 24, 4045-4049.
[5] Johnson P.D.;Sohn J.-H.; Rawal, V.H. J. Org. Chem. 2006, 71, 7899-902.
[6] US 10,351,504 B1, 2019; Washington, DC: U.S. Patent and Trademark Office.
[7] (a) Wang, Y.; Pi, C.; Wu, Y.-G.; Cui, X.-L. Chemistry (Weinheim an der Bergstrasse, Germany), 2024, 30, e202402974.(b) Black, D. S. C.; Rothnie, N E.; Wong, L. C. H. Tetrahedron Letters. 1980, 19, 1883-1886. 1996, 13, 4697-4708.(d) Xie, X.-L.; Liu, G.-Z.; Niu, Y.-X.; Xu, C.-H.; Li, Y.; Zhang, G.; Jiao, X.-Y.; Wang, X.; Tang, B. Anal Chem. 2021, 93, 15088-15095.(e) Wang, Y., Li, Y., Chen, H. Nat Commun. 2024, 15, 6183. 2023, 88, 5520-5529.
[8] (a) Li, S.-W.; Gong, J.; Kang, Q. Org. Lett. 2017, 19, 1350-1353.(b) Ren, Y.-Z.; Lu, S.-H; He, L.; Zhao, Z.-F.; Li, S.-W. Org. Lett. 2022, 24, 2585-2589. (c) Zhu, S.-J.; Tian, X.; Li, S.-W. Org. Lett. 2024, 26, 6309-6313. 2024, 26, 9237-9243.
[9] (a) Cheng, D. P.; Gu, H. F.; Xia, H. S.; Wang, Y.W.; Li, J.-H.; Xu, X. L. Synlett. 2023, 34, 2309-2314.(b) Gao Xi, Li Chengwen, Chen Li, Li Xin. Org. Lett.2023, 25, 7628-7632. (c) Woldegiorgis, A. G.; Han, Z.; Lin, X.-F. Org. Lett. 2022, 24, 4058-4063. (d) Li, J.-H.; Duan, X.-Y.; Ren, X.-J.; Li, Y.-T.; Qi, J. J. Org. Chem. 2023, 88, 16621-16632. (e) Ji, X.; Zhu, S.-J.; Li, Y.-S.; Zhao, Z.-F.; Li. S.-W. Org. Chem. Front. 2024, 11, 5385-5389. (f) Tang, M.-D.; Wang, M.; Li, S.-Y.; Guo, C.-X.; Song, R.; Yang, D.-S.; Lv, J. Org. Lett. 2024, 26, 32, 6894-6899.
[10] (a) Khurana, J. M.; Kandpal, B. M. Tetrahedron Lett, 2003, 26, 4909-4912.(b) Wang, Z.-L.; An, X.-L.; Ge, L.-S.; Jin, J.-H.; Luo, X. Y.; Deng, W.-P. Tetrahedron. 2014, 70, 3788-3792. (c) Yang, Y.; Qiang, S.; Hui, C.; Chandler, K. S. Doyle, M. P. Org. Lett. 2018, 20, 776-779. (d) Hu, W. L.; Huang, B.; Niu, B.B.; Cai, M.Z. Tetrahedron Lett, 2021, 68, 152953.
[11] (a) Li, L. J.; He, Y. L.; Yang, Y. H.; Guo, J.; Lu, Z.; Wang, C. Y.; Zhu, S. L.; Zhu, S. F. CCS Chem. 2024, 6, 537-584.(b) Liu, P.; Wu, B. W.; Cong, X. F.; Kong, J. Chin. J. Chem. 2024, 42, 578-584. (c) Shi, C. Q.; Wang, E. H.; Zhang, Y. X.; Ma, T. Y.; Zhang, R. C.; Huang, H.; He, Y.; Peng, Q.; Feng, Z. CCS Chem. 2025, DOI: 10.31635/ccschem.025.202505855. (d) Wang, L. T.; Li, M. H.; Yan, H. C.; Cheng, Z. Y.; Lu, Z. Chin. J. Chem. 2025, 43, 3496-3500.

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FeCl₃催化的含吡唑骨架与叔醇酯基杂环化合物的构建

FeCl₃-Mediated Assembly of heterocyclic compounds containing both pyrazole scaffolds and tertiary alcohol ester moieties

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FeCl3催化的含吡唑骨架与叔醇酯基杂环化合物的构建