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

Mostafa, Isbera and Balázs, Bognár and Ferenc, Gallyas and Attila, Bényei and József, Jekő and Tamás, Kálai (2021) Syntheses and study of a pyrroline nitroxide condensed phospholene oxide and a pyrroline nitroxide with diphenylphosphino moiety. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 197 (5-6). pp. 515-517. ISSN 1042-6507

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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.

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