Reaction strategies for the meta-selective functionalization of pyridine through dearomatization
- PMID: 38647989
- DOI: 10.1007/s11030-024-10861-5
Reaction strategies for the meta-selective functionalization of pyridine through dearomatization
Abstract
The pyridine moiety is a crucial structural component in various pharmaceuticals. While the direct ortho- and para-functionalization of pyridines is relatively straightforward, the meta-selective C-H functionalization remains a significant challenge. This review highlights dearomatization strategies as a key area of interest in expanding the application of meta-C-H functionalization of pyridines. Dearomatization enables the meta-functionalization through various catalytic methods that directly generate dearomatization products, and some products can be rearomatized back to pyridine derivatives. Furthermore, this article also covers the dearomatization of multiple positions of pyridine in the synthesis of polycyclic compounds. It offers a comprehensive overview of the latest advancements in dearomatization at different positions of pyridine, aiming to provide a valuable resource for researchers in this field. It also highlights the advantages and limitations of existing technologies, aiming to inform a broader audience about this important field and foster its future development.
Keywords: C3-functionalization; Dearomatization; Pyridine; Reaction strategy; Reduction.
© 2024. The Author(s), under exclusive licence to Springer Nature Switzerland AG.
Conflict of interest statement
Declarations. Competing interests: The authors declare no competing interests.
Similar articles
-
meta-Selective C-H Functionalization of Pyridines.Angew Chem Int Ed Engl. 2023 Oct 16;62(42):e202302941. doi: 10.1002/anie.202302941. Epub 2023 Jul 13. Angew Chem Int Ed Engl. 2023. PMID: 37013613 Review.
-
C-H Functionalization of Pyridines via Oxazino Pyridine Intermediates: Switching to para-Selectivity under Acidic Conditions.J Am Chem Soc. 2023 Jul 19;145(28):15581-15588. doi: 10.1021/jacs.3c05242. Epub 2023 Jul 10. J Am Chem Soc. 2023. PMID: 37428649
-
Advances in Pyridine C-H Functionalizations: Beyond C2 Selectivity.Chemistry. 2025 Jan 9;31(2):e202403032. doi: 10.1002/chem.202403032. Epub 2024 Dec 10. Chemistry. 2025. PMID: 39604069 Review.
-
Highly Enantioselective Nucleophilic Dearomatization of Pyridines by Anion-Binding Catalysis.Angew Chem Int Ed Engl. 2015 Jul 20;54(30):8823-7. doi: 10.1002/anie.201502708. Epub 2015 Jun 25. Angew Chem Int Ed Engl. 2015. PMID: 26111052
-
Ortho C-H Functionalization of 2-Arylimidazo[1,2-a]pyridines.Chem Rec. 2022 Mar;22(3):e202100240. doi: 10.1002/tcr.202100240. Epub 2021 Nov 10. Chem Rec. 2022. PMID: 34757691 Review.
References
-
- Guillemard L, Kaplaneris N, Ackermann L, Johansson MJ (2021) Late-stage C–H functionalization offers new opportunities in drug discovery. Nat Rev Chem 5:522–545. https://doi.org/10.1038/s41570-021-00300-6 - DOI - PubMed
-
- De S, Kumar SKA, Shaha SK, Kazia S, Sarkara N, Banerjeec S, Dey S (2022) Pyridine: the scaffolds with significant clinical diversity. RSC Adv 12:15385–15406. https://doi.org/10.1039/D2RA01571D - DOI - PubMed - PMC
-
- Cannalire R, Pelliccia S, Sancineto L, Novellino E, Tron GC, Giustiniano M (2021) Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds. Chem Soc Rev 50:766–897. https://doi.org/10.1039/D0CS00493F - DOI - PubMed
-
- Zhang Y, Pike A (2021) Pyridones in drug discovery: recent advances. Bioorg Med Chem Lett 38:127849. https://doi.org/10.1016/j.bmcl.2021.127849 - DOI - PubMed
-
- Wencel-Delord J, Glorius F (2013) C–H bond activation enables the rapid construction and late-stage diversification of functional molecules. Nat Chem 5:369–375. https://doi.org/10.1038/nchem.1607 - DOI - PubMed
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Miscellaneous