Reactions of Nitroxides. Part IXa. Reactive (Thio)Phosphoryl Mono- chlorides Bearing a Nitroxyl Moiety and Nitroxyl Derivatives of Coumarin

Title: Reactions of Nitroxides. Part IXa. Reactive (Thio)Phosphoryl Mono- chlorides Bearing a Nitroxyl Moiety and Nitroxyl Derivatives of Coumarin

Volume: 7 Issue: 7

Author(s): Bogumila Huras, Jerzy Zakrzewski and Maria Krawczyk

Affiliation:

Keywords: Coumarin derivatives, nitroxyl radicals, organophosphorus compounds

Abstract: Reactive intermediates – (thio)phosphoryl monochlorides bearing a nitroxyl moiety were synthesized from either 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl or 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, and (thio)phosphoryl dichlorides in the presence of triethylamine, DMAP or DABCO in 26-62% yield. Synthesized (thio)phosphoryl monochlorides were condensed with potassium salt of 3-chloro-7-hydroxy-4-methylcoumarin affording phosphorylated coumarin derivatives bearing a nitroxyl moiety in 57-92% yield. Antifungal activity of synthesized nitroxyl derivatives of coumarin was found.

Cite this article as:

Huras Bogumila, Zakrzewski Jerzy and Krawczyk Maria, Reactions of Nitroxides. Part IXa. Reactive (Thio)Phosphoryl Mono- chlorides Bearing a Nitroxyl Moiety and Nitroxyl Derivatives of Coumarin, Letters in Organic Chemistry 2010; 7 (7) . https://dx.doi.org/10.2174/157017810793362325