3-氰基吡啶类化合物的合成与应用研究进展

doi:10.6023/cjoc202512034

摘要/Abstract

3-氰基吡啶(烟腈)类化合物作为一类多功能分子备受关注, 不仅具有抗肿瘤、抗菌等广泛的药理活性, 在光学材料领域也有着广泛的应用, 同时还是许多化合物制备过程中的重要合成子. 基于此, 综述了近10年来该类化合物的合成进展, 重点介绍了通过多组分反应、新型环化和官能团转化策略制备3-氰基吡啶类化合物的研究进展, 并梳理3-氰基吡啶类化合物在合成化学、药物化学、材料化学等领域的应用. 展望未来, 借助光、电催化等绿色合成技术合成3-氰基吡啶类化合物, 并以此为基础开发性能优异的荧光探针分子、新能源材料等仍是研究的重点.

关键词: 多组分反应, 3-氰基吡啶, 绿色合成, 合成子, 生物活性, 荧光探针

3-Cyanopyridine (nicotinonitrile) compounds have garnered significant attention as versatile molecular scaffolds due to their broad pharmacological activities, including antitumor and antibacterial effects, as well as their extensive appli- cations in optical materials. Furthermore, they serve as crucial synthetic intermediates in the preparation of various com- pounds. This review summarizes the synthetic advances of these compounds over the past decade, with an emphasis on the construction of the 3-cyanopyridine framework through multicomponent reactions, novel cyclization strategies, and functional group transformations. Additionally, the applications of 3-cyanopyridine compounds in synthetic chemistry, medicinal che- mistry, and materials science are systematically outlined. Looking forward, the development of photo- and electrocatalytic green synthetic methodologies for 3-cyanopyridine compounds, along with the exploration of high-performance fluorescent probes and new energy materials based on these scaffolds, remains a key research focus.

Key words: multi-component reaction, 3-cyanopyridine, green synthesis, synthon, bioactivity, fluorescent probe

引用此文

陈珪媛, 李晟宇, 郭基林, 王相, 刘烨潼, 肖贝宁, 汪朝阳. 3-氰基吡啶类化合物的合成与应用研究进展[J]. 有机化学, 2026, 46(6): 2227-2240.

Guiyuan Chen, Shengyu Li, Jilin Guo, Xiang Wang, Yetong Liu, Beining Xiao, Zhaoyang Wang. Research Progress in Synthesis and Application of 3-Cyanopyridines[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2227-2240.

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图/表 21

图式1. 四组分反应合成3-氰基吡啶类化合物3及其机理

Scheme 1. Reaction of four components to synthesize 3-cyanopyridine compounds and its mechanism

图式2. 肟基作为氮源一锅法合成3-氰基吡啶类化合物及其机理

Scheme 2. One-pot synthesis of 3-cyanopyridine compounds using oxime as a nitrogen source and its mechanism

图式3. 基于活性亚甲基化合物合成3-氰基吡啶类化合物及机理(以氰基乙酸乙酯为例)

Scheme 3. Mechanism of synthesizing 3-cyanopyridine compounds based on active methylene compounds (taking the ethyl cyanoacetate as an example)

图式4. 生物基离子液体NMS的合成及其在3-氰基吡啶类化合物合成中的应用

Scheme 4. Synthesis of bio-based ionic liquid NMS and its application in the synthesis of 3-cyanopyridine compounds

图式5. [TSPi][Cl]2催化一锅两步法合成2-氨基-3-氰基吡啶

Scheme 5. One-pot, two-step synthesis of 2-amino-3-cyanopyridines catalyzed by [TSPi][Cl]2

图式6. 具有抗癌活性的2-氨基-3-氰基吡啶类化合物的合成

Scheme 6. Synthesis of 2-amino-3-cyanopyridine compounds with anticancer activity

图式7. 查尔酮与不同环化试剂反应合成3-氰基吡啶类化合物

Scheme 7. Synthesis of 3-cyanopyridine compounds from the reaction of chalcones with different cyclizing reagents

图式8. 基于2-乙酰基噻吩的查尔酮环化反应

Scheme 8. Cyclization reaction of chalcones based on 2-acetylthiophene

图式9. 色酮开环偶联策略合成3-氰基吡啶类化合物及其可能机理

Scheme 9. Synthesis of 3-cyanopyridine compounds via chromone ring-opening coupling strategy and its possible mechanism

图式10. 多取代2-氨基-3-氰基吡啶的构建及其机理(以苄胺为例)

Scheme 10. Construction of multi-substituted 2-amino-3-cyanopyridines and its mechanism (using benzylamine as an example)

图式11. 三取代氰基吡啶的合成及其机理(以哌啶为例)

Scheme 11. Synthesis of trisubstituted cyanopyridines and its mechanism (taking piperidine as an example)

图式12. O-烷基化反应合成2-烷氧基-3-氰基吡啶类化合物

Scheme 12. O-Alkylation reaction for the synthesis of 2-alkoxy-3-cyanopyridine compounds

图式13. POCl3介导氰基吡啶酮中间体氯化反应构建3-氰基吡啶类化合物

Scheme 13. POCl3-mediated chlorination of cyano-pyridone intermediates to construct 3-cyano-pyridines

图式14. 基于嘧啶环重排的环转化策略合成2-氨基-3-氰基吡啶及其机理

Scheme 14. Pyrimidine ring rearrangement based cycloconversion strategy for the synthesis of 2-amino-3-cyanopyridine and its mechanism

图式15. 以2-氨基-3-氰基吡啶为原料合成4,6-二苯基-2-(1H-吡咯-1-基)烟腈衍生物

Scheme 15. Synthesis of 4,6-diphenyl-2-(1H-pyrrol-1-yl)nicotinonitrile derivatives from 2-amino-3-cyanopyridine as starting material

图式16. 2-氨基-3-氰基吡啶中间体13的衍生化反应

Scheme 16. Derivatization reactions of 2-amino-3-cyanopyridine intermediates 13

图1. 一些具有生物活性的3-氰基吡啶类化合物的结构

Figure 1. Structures of some 3-cyanopyridine compounds with biological activities

图2. 一些含3-氰基吡啶单元的D-A (D-π-A)型光学材料的结构

Figure 2. Structures of some D-A (D-π-A) type optical materials containing 3-cyanopyridine unit

图式17. 探针21的合成与检测机理

Scheme 17. Synthesis and detection mechanism of probe 21

图式18. 探针22的合成与检测机理

Scheme 18. Synthesis and detection mechanism of probe 22

图式19. 2-吗啉基-4,6-二甲基烟腈探针23的合成

Scheme 19. Synthesis of 2-morpholino-4,6-dimethyl nicotinonitrile probe 23

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