Reactions of 2- and 4-pyrones with secondary phosphine chalcogenides: a facile synthesis of functional phosphorylated pyrones

• Published in: Tetrahedron letters Vol. 54; no. 49; pp. 6772 - 6775
• Main Authors: Gusarova, Nina K., Volkov, Pavel A., Ivanova, Nina I., Sukhov, Boris G., Larina, Ludmila I., Kazheva, Olga N., Alexandrov, Grigorii G., D’yachenko, Oleg A., Trofimov, Boris A.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 04-12-2013
• Subjects: 2-Pyrone; 4-Pyrone; Carbon tetrachloride; Chalcogenides; Cross coupling; Hydroxyl groups; Phosphines; Phosphinoсhalcogenоic O-esters; Phosphorylation; Secondary phosphine chalcogenides; Synthesis (chemistry); Tetrahedrons; 4-Pyrone; Phosphorylation; 2-Pyrone; Secondary phosphine chalcogenides; Phosphinoсhalcogenоic O-esters
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2013.10.016

The oxidative cross-coupling between 4-hydroxy-6-methyl-2-pyrone or 3-hydroxy-2-methyl-4-pyrone and secondary phosphine chalcogenides proceeds in CCl4/Et3N under mild conditions (20–52°С, 0.75–10h) through the hydroxyl group to give O-(6-methyl-2-oxo-2H-pyran-4-yl) diorganylphosphinochalcogenoates or O-(2-methyl-4-oxo-4H-pyran-3-yl) diorganylphosphinochalcogenoates, in high yields.