关于8种含氮杂环光催化合成的研究进展

doi:10.6023/cjoc202505018

有机化学 ›› 2025, Vol. 45 ›› Issue (10): 3546-3586.DOI: 10.6023/cjoc202505018 上一篇下一篇

综述与进展

关于8种含氮杂环光催化合成的研究进展

刘艺琦^a, 陈文婕^a, 赵泽艳^a, 王苏棋^a, 唐圣松^b^,^*(), 何卫民^a^,^*(), 彭俊梅^a^,^*()

^a 南华大学衡阳医学院药学院湖南衡阳 421001
^b 湖南医药学院新型抗体药物及其智能运输系统湖南省重点实验室湖南怀化 410007

收稿日期:2025-07-22 修回日期:2025-08-24 发布日期:2025-09-17
基金资助:
湖南省自然科学基金(2023JJ30525); 湖南省教育厅科研项目(22A0295); 新型抗体药物及其智能运输系统湖南省重点实验室开放课题项目(2023-KL02); 湖南省卫健委科研项目(D202313057620); 2024年大学生创新创业训练计划(S202410555025)

Research Progress on Photocatalytic Synthesis of Eight Nitrogen-Containing Heterocycles

Yiqi Liu^a, Wenjie Chen^a, Zeyan Zhao^a, Suqi Wang^a, Shengsong Tang^b^,^*(), Wei-Min He^a^,^*(), Junmei Peng^a^,^*()

^a Department of Pharmaceutical Chemistry, School of Pharmacy, Hengyang Medical School, University of South China, Hengyang, Hunan 421001
^b Hunan Province Key Laboratory for Antibody-based Drug and Intelligent Delivery System, School of Pharmaceutical Sciences, Hunan University of Medicine, Hunan 410007

Received:2025-07-22 Revised:2025-08-24 Published:2025-09-17
Contact: * tangss_submit@163.com; weiminhe@usc.edu.cn; pengmarina@126.com
Supported by:
Hunan Provincial Natural Science Foundation(2023JJ30525); Hunan Provincial Department of Education Scientific Research Project(22A0295); Hunan Province Key Laboratory for Antibody-Based Drug and Intelligent Delivery System(2023-KL02); Hunan Provincial Health Commission Scientific Research Project(D202313057620); 2024 College Student Innovation and Entrepreneurship Training Program(S202410555025)

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摘要/Abstract

含氮杂环因其独特的结构特征表现出广泛的药理活性, 它常用于药物、农用化学品和先进材料的结构修饰. 含氮杂环化合物的合成是现代有机化学中一个关键且迅速发展的领域. 近年来, 光催化方法作为一种环境友好且高效的合成策略逐渐兴起, 为构建多种杂环结构提供了新的途径, 并为药物分子的合成开辟了新的思路. 综述了近五年来光催化合成8类不同含氮杂环化合物的高效方法.

关键词: 含氮杂环, 光催化, 合成方法

Nitrogen-containing heterocycles display a wide range of pharmacological activities attributable to their distinctive structural characteristics. They are frequently employed in the structural modification of pharmaceuticals, agrochemicals, and advanced materials. The synthesis of nitrogen-containing heterocyclic compounds represents a crucial and rapidly evolving domain within modern organic chemistry. In recent years, photocatalytic approaches have emerged as an environmentally benign and highly efficient synthetic strategy. This has provided novel pathways for constructing diverse heterocyclic architectures and has opened up new perspectives for the synthesis of drug molecules. This article reviews the efficient methods for the photocatalytic synthesis of eight different types of nitrogen-containing heterocyclic compounds in the past five years.

Key words: nitrogenous heterocycles, photocatalysis, synthesis method

引用此文

刘艺琦, 陈文婕, 赵泽艳, 王苏棋, 唐圣松, 何卫民, 彭俊梅. 关于8种含氮杂环光催化合成的研究进展[J]. 有机化学, 2025, 45(10): 3546-3586.

Yiqi Liu, Wenjie Chen, Zeyan Zhao, Suqi Wang, Shengsong Tang, Wei-Min He, Junmei Peng. Research Progress on Photocatalytic Synthesis of Eight Nitrogen-Containing Heterocycles[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3546-3586.

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图/表 63

Figure 1. Drugs containing benzimidazole backbone

Scheme 1. Philips-Sladenburg method for the synthesis of benzimidazole

Scheme 2. Hypercrosslinked polymers used as a photocatalyst to synthesize benzimidazoles

Scheme 3. Acr-Mes＋ClO4 polymers used as a photocatalyst to synthesize benzimidazoles

Scheme 4. Fe-CPTP sed as a photocatalyst to synthesize benzimidazoles

Scheme 5. PAF-366 used as a photocatalyst to synthesize benzimidazoles

Scheme 6. NQ-COFD4-Me used as a photocatalyst to synthesize benzimidazoles

Scheme 7. NQ-COFD4-Me used as a photocatalyst to synthesize benzimidazoles

Scheme 8. Fe3O4@V/TiO2 used as a photocatalyst to synthesize benzimidazoles

Scheme 9. BDFe-COF used as a photocatalyst to synthesize benzimidazoles

Scheme 10. Benzimidazole compounds synthesized without photocatalysts

Scheme 11. Photochemical conversion of indazoles into benzimidazoles

Scheme 12. Benzimidazole compounds synthesized using indole as the backbone

Scheme 13. Benzimidazole compounds synthesized using indazole as the backbone

Figure 2. Drugs containing indole backbone

Scheme 14. 4-CzIPN as a photocatalyst for the synthesis of indole compounds

Scheme 15. Indoles synthesis without a photocatalyst

Scheme 16. TBADT as a photocatalyst for the synthesis of indole compounds

Scheme 17. [Mes-Acr-Me]＋ClO4 as a photocatalyst for the synthesis of indole compounds

Scheme 18. Selective carbon deletion directly produces indole

Figure 3. Drugs containing benzothiazole backbone

Scheme 19. g-C3N4 as a photocatalyst for the synthesis of benzothiazole compounds

Scheme 20. Synthesis of benzothiazole compounds without the action of a photocatalyst

Scheme 21. Fluorescein as a photocatalyst for the synthesis of benzothiazole compounds

Scheme 22. Eosin Y as a photocatalyst for the synthesis of benzothiazole compounds

Scheme 23. MOF-1(Co) as a photocatalyst for the synthesis of benzothiazole compounds

Scheme 24. g-C3N4 as a photocatalyst for the synthesis of benzothiazole compounds

Scheme 25. RFTA as a photocatalyst for the synthesis of benzothiazole compounds

Scheme 26. UiO-68-BTDB as a photocatalyst for the synthesis of benzothiazole compounds

Scheme 27. Fe3O4@Diol-AHEB-CuCl2 as a photocatalyst for the synthesis of benzothiazole compounds

Scheme 28. Photocatalytic boron insertion into thiaarenes via boryl radicals

Figure 4. Drugs containing a triazole skeleton

Scheme 29. Synthesis of triazoles using Ru(bpy)3Cl2 as a photocatalyst

Scheme 30. Synthesis of triazoles using TiO2-Cu2(OH)PO4 as a photocatalyst

Scheme 31. Synthesis of triazoles using Eosin Y as a photocatalyst

Scheme 32. Synthesis of triazoles using Rh-6G as a photocatalyst

Figure 5. Drugs containing a pyrrolidine backbone

Scheme 33. TBAI3-mediated [3＋2] cycloaddition reaction under photocatalytic conditions

Scheme 34. PC-B is a photocatalyst for the synthesis of pyrrolidine compounds

Scheme 35. Synthesis of fluoroalkylated pyrrolidines through neat reaction of fluoroalkyl iodides with N,N-diallylamines

Scheme 36. Synthesis of dihydropyrrolidines using Ru(bpy)3(BF4)2 as a photocatalyst

Scheme 37. 4CzIPN as a photocatalyst for the synthesis of pyrrolidine compounds

Scheme 38. Photocatalytic synthesis of 4-pyrroline-2-one

Figure 6. Drugs containing a pyrimidine backbone

Scheme 39. Synthesis of pyrimidine compounds using KPCN as a photocatalyst

Scheme 40. One-pot synthesis of fluorinated pyrimidine derivatives

Figure 7. Drugs containing a quinoline backbone

Scheme 41. Synthesis of multi-substituted quinolines using CuCl as a Photocatalyst

Scheme 42. Synthesis of multi-substituted quinolines using PQ as a photocatalyst

Scheme 43. Synthesis of quinoline compounds using a dual-catalytic system

Scheme 44. Synthesis of quinoline compounds with Eosin Y as a photocatalyst

Scheme 45. Synthesis of C-3 aminoquinolin-2(1H)-one via photocatalytic denitrogenative skeletal rearrangement

Scheme 46. Semi-heterogeneous photoredox catalytic synthesis of 3-sulfonylquinolines

Scheme 47. Synthesis of 2-(3-cyanoalkyl) substituted quinoline derivatives using fac-Ir(ppy)3 as a photocatalyst

Scheme 48. Multi-substituted quinolines and quinazolines with NDI as the photocatalyst

Figure 8. Drugs containing a quinazoline backbone

Scheme 49. Quinazoline compounds synthesized by RB as a photocatalyst

Scheme 50. Synthesis of quinazoline compounds with CALB and Eosin Y as co-catalysts

Scheme 51. Synthesis of quinazoline compounds with PC as the photocatalyst

Scheme 52. Synthesis of quinazoline compounds via a catalyst-free one-pot three-component method

Scheme 53. Synthesis of 2-substituted quinazoline derivatives via synergistic catalysis of visible light and organoselenium

Scheme 54. Synthesis of quinazoline compounds using Eosin Y as a photocatalyst

Scheme 55. One-pot synthesis of quinazolines using lignin-derived carbon-coated CuO

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关于8种含氮杂环光催化合成的研究进展

Research Progress on Photocatalytic Synthesis of Eight Nitrogen-Containing Heterocycles

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