Research Progress in Synthesis and Application of 3-Cyanopyridines

doi:10.6023/cjoc202512034

Abstract

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

Cite this article

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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Fig. & Tab. 21

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 17. Synthesis and detection mechanism of probe 21

Scheme 18. Synthesis and detection mechanism of probe 22

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

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