A team of authors from the Research Group of Advanced Materials and Organic Synthesis published a new method for the synthesis of previously undescribed phosphorus-heterocyclic compounds in The Journal of Organic Chemistry. The developed procedure enables the efficient preparation of so-called quinolizidine 1,4-azaphosphinines – structurally unique six-membered heterocycles containing phosphorus and nitrogen atoms.
The key step is the intramolecular cyclization of appropriately prepared phosphinates catalyzed by silver trifluoroacetate. The reaction occurs under mild conditions and involves simultaneous hydroarylation of the alkyne and dearomatization of the pyridine ring. This approach allows the formation of a complex bicyclic system in a single synthetic step.
The method exhibits wide substrate variability and has been successfully applied to dozens of different derivatives. The resulting structures represent a new type of phosphorus heterocycles that can find application, for example, in the research of biologically active substances and functional materials, as well as in the field of coordination chemistry. The biological activity of the prepared compounds will be further tested in collaboration with BASF, allowing assessment of their potential for practical applications.
- Kos M., Beránek T., Žádný J., Kochová N., Václavíková K., Panov I., Storch J., Císařová I., Sýkora J., and Církva V.: Synthesis of Quinolizidine-Based 1,4-Azaphosphinines via Cyclization of Heteroarylmethyl(alkynyl)phosphinates J. Org. Chem. 2026, 91(1), 698-719. doi.org/10.1021/acs.joc.5c02870