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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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 and Maria Krawczyk

Volume 7, Issue 7, 2010

Page: [545 - 551] Pages: 7

DOI: 10.2174/157017810793362325

Price: $65

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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