Herein we present the regio- and diastereoselective synthesis of novel pyrrolidine-fused spiro-dihydrophosphacoumarins via intermolecular [3 + 2] cycloaddition reaction. The presented approach is complementary to existing ones and provides an easy entry to the otherwise inaccessible derivatives. Additionally, the unprecedented pathway of the reaction of 4-hydroxycoumarin with azomethine ylides is described. The anti-cancer activity of the obtained compounds was tested in vitro, the most potent compound being 2.6-fold more active against the HuTu 80 cell line than the reference 5-fluorouracil, with a selectivity index > 32.

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New intramolecular cyclization of 2H-benzo[e]-1,2-oxaphosphorinine derivatives—a way to the synthesis of unsymmetrical cage phosphonates

Diastereoselective Synthesis of Novel Spiro-Phosphacoumarins and Evaluation of Their Anti-Cancer Activity

It was found that the reaction of 2-hydroxy-5,7,8-trimethyl-2H-1,2-benzoxaphosphinine 2-oxide with resorcinol and its derivatives as well as sesamol leads to the formation of phosphaneoflavanones in high yields. The obtained phosphaneoflavanones are precursors in the synthesis of novel unsymmetrical cage phosphonates. The structures of the obtained products were confirmed by IR spectroscopy, 1H, 13C NMR spectroscopy, and X-ray structural analysis.

New intramolecular cyclization of 2H-benzo[e]-1,2-oxaphosphorinine derivatives—a way to the synthesis of unsymmetrical cage phosphonates

Citations

Diastereoselective Synthesis of Novel Spiro-Phosphacoumarins and Evaluation of Their Anti-Cancer Activity

References

Synthesis of unsymmetrical cage phosphonates from heterocyclic systems based on 2H-1,2-benzoxaphosphinine

New bicyclic phosphonates of unsymmetrical structure