Reactions of nitroxides, part XI: <i>O</i>‐Aryl phenylselenophosphonates bearing a nitroxyl moiety

Huras, Bogumiła; Zakrzewski, Jerzy; Krawczyk, Maria

doi:10.1002/hc.20667

Cited by 20 publications

(1 citation statement)

References 28 publications

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“…The references for the synthesis of the following nitroxyl amines: 3-amino-2,2,5,5-tetramethylpyrrolidine-1-oxyl, PROXYL-NH 2 ( 2h ), 3-aminomethyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl PROXYL-CH2-NH 2 ( 2i ), 4-amino-2,2,6,6-tetramethylppiperidine-1-oxyl, TEMPO-NH 2 ( 2j ) have been recently cited [85]. The references for the synthesis of 4-hydroxy-2,2,6,6-tetramethylppiperidine-1-oxyl (TEMPOL ( 3c )) was cited [88]. TLC was carried out on silica gel Merck Alurolle 5562 or Alufolien 5554; TLC visualization was achieved using UV 254 nm light and/or I 2 vapor; visualization of selenium containing compounds: UV 254 nm and irradiation with UV lamp for 5–10 min (red spots) or spraying with 1% ethanolic PdCl 2 (dark brown spots on pale beige background).…”

Section: Methodsmentioning

confidence: 99%

Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

et al. 2019

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The reactions of 3-isoselenocyanato-2,2,5,5-tetramethylpyrrolidine-1-oxyl, 3-isoselenocyanatomethyl-2,2,5,5-tetramethyl-3-pyrrolidine-1-oxyl, and 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl with selected amines and alcohols give the corresponding novel nitroxyl selenoureas and selenocarbamates, all bearing a nitroxyl moiety. Synthesized selenoureas and selenocarbamates show significant activity against pathogenic fungi and bacteria. In contrast to piperidine nitroxides, pyrrolidine, five-membered nitroxyl selenoureas and selenocarbamates show excellent antifungal and antibacterial activity against pathogenic fungi and bacteria, respectively.

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Section: Methodsmentioning

confidence: 99%

Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

et al. 2019

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Organic Compounds Containing Bonds between Se or Te with P, As, Sb and Bi

Murai

2014

Patai's Chemistry of Functional Groups

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This chapter describes syntheses, structures, and reactions of the compounds with phosphorus‐selenium double bonds and with at least one carbon‐phosphorus single bond and of their heavier congeners. Among them, phosphane selenides have been the most deeply studied and used as Lewis base catalysts, metal ligands, molecular sensors, and stating materials leading to selenium‐containing nanoparticles. The coupling constants between the phosphorus and selenium atoms are informative on the basicity of the phosphanes. Phosphinoselenoic acid chlorides and secondary phosphanes are frequently used precursors to give a range of phosphinoselenoic acid derivatives, whereas selenation of dichlorophosphanes leads to phosphonoselenoic acid dichlorides, which are converted to a variety of acid derivatives. The selenation of phosphinites also gives phosphinoselenoic acid O ‐esters. Stereochemical course of the substitution reaction at P ‐chiral phosphorus center in the substitution reaction has been elucidated. Some reactions of dimers of diselenoxophosphanes such as Woollin's reagent are also shown. The chapter finally describes examples of phosphane tellurides, arsenic, antimony, and bismuth isologues of phosphane selenides, although these are fewer.

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ChemInform Abstract: Reactions of Nitroxides. Part 11. O‐Aryl Phenylselenophosphonates Bearing a Nitroxyl Moiety.

Huras¹,

Zakrzewski²,

Krawczyk³

2011

ChemInform

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Reactions of Nitroxides. Part 11. O-Aryl Phenylselenophosphonates Bearing a Nitroxyl Moiety. -Reaction of TEMPOL (I) with phenyldichlorophosphine selenide (II) and phenols gives the title selenophosphonates (IV) as the major products. Some of them and related diaryl selenophosphonates (V) display weak to good antifungal activities. -(HURAS, B.; ZAKRZEWSKI*, J.; KRAWCZYK, M.; Heteroat. Chem. 22 (2011) 2, 137-147, http://dx.doi.org/10.1002/hc.20667 ; Inst. Ind. Org. Chem., PL-03-236 Warsaw, Pol.; Eng.) -A. Forchert 29-176

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Reactions of nitroxides, part XI: O‐Aryl phenylselenophosphonates bearing a nitroxyl moiety

Cited by 20 publications

References 28 publications

Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

Organic Compounds Containing Bonds between Se or Te with P, As, Sb and Bi

ChemInform Abstract: Reactions of Nitroxides. Part 11. O‐Aryl Phenylselenophosphonates Bearing a Nitroxyl Moiety.

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