Syntheses and Study of a Pyrroline Nitroxide Condensed Phospholene Oxide and a Pyrroline Nitroxide Attached Diphenylphosphine.

Mostafa Isbera,Tamás Kálai,Attila Bényei,József Jekő,Ferenc Gallyas,Balázs Bognár

doi:10.3390/molecules26144366

Mostafa Isbera, Tamás Kálai + Show 4 more

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https://doi.org/10.3390/molecules26144366

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Abstract

The reaction of a diene nitroxide precursor with dichlorophenylphosphine in a McCormac procedure afforded 1,1,3,3-tetramethyl-5-phenyl-1,2,3,4,5,6-hexahydrophospholo[3,4-c]pyrrole-5-oxide-2-oxyl. Lithiation of the protected 3-iodo-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 is an analogue of antineoplastic agent, MITO-CP.

Highlights

Heterocyclic nitroxide derivatives of piperidine pyrrolidine, pyrroline and imidazoline have found various applications [1,2]
Nitroxides have a wide range of applications; they are used as co-oxidants in organic chemistry, building blocks for magnetic materials, superoxide dismutase mimics, antiproliferative compounds, mediators of polymerization, redox active materials in batteries, magnetic resonance imaging (MRI), and electron paramagnetic resonance imaging (EPRI)
In continuation of our interest in the synthesis of nitroxide-based phosphorus compounds, we have promoted the synthesis of phosphorus-containing heterocycles condensed with pyrroline nitroxide and pyrroline nitroxide-diphenylphosphine and pyrroline nitroxidediphenylphosphine oxide compounds

Summary

Introduction

Heterocyclic nitroxide derivatives of piperidine pyrrolidine, pyrroline and imidazoline have found various applications [1,2]. Nitroxides have a wide range of applications; they are used as co-oxidants in organic chemistry, building blocks for magnetic materials, superoxide dismutase mimics, antiproliferative compounds, mediators of polymerization, redox active materials in batteries, magnetic resonance imaging (MRI), and electron paramagnetic resonance imaging (EPRI). Contrast agents [1,2] These various applications require numerous paramagnetic scaffolds adjusted to different utilizations. Our idea is to combine various phosphorus-containing functional groups with nitroxides, which may offer fascinating possibilities for synthetic, structural and biological studies and the utilization of these new compounds [6,7]. Similar nitroxides have been previously reported with nitronyl nitroxides [8] and a phosphorus-containing heterocycle [9], our Molecules 2021, 26, 4366.

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