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

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

Journal Name: Letters in Organic Chemistry

Volume 7 , Issue 7 , 2010

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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.

Keywords: Coumarin derivatives, nitroxyl radicals, organophosphorus compounds

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Article Details

VOLUME: 7
ISSUE: 7
Year: 2010
Page: [545 - 551]
Pages: 7
DOI: 10.2174/157017810793362325
Price: $65

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