Syntheses and study of a pyrroline nitroxide condensed phospholene oxide and a pyrroline nitroxide with diphenylphosphino moiety

Abstract

The reaction of a diene nitroxide precursor with dichlorophenylphosphine in a McCormac procedure afforded pyrroline nitroxide condensed phospholen oxide. Lithiation of the protected 3-bromo-pyrroline nitroxide followed by treatment with chlorodiphenylphosphine after deprotection afforded (1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)diphenylphosphine oxide, and after reduction, (1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)diphenylphosphine was realized, which was also supported by X-ray single crystal diffraction measurements. This pyrroline diphenylphosphine derivative was converted to hexadecylphosphonium salt, which was more effective antineoplastic agent than its analogue MITO-CP.

Graphical Abstract

Keywords:

• Lithiation
• McCormac reaction
• nitroxides
• protecting groups
• reduction

Additional information

Funding

The study was financed by Hungarian National Research Development and Innovation Office NKFI-137793.