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

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)phos- phoryl 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.