7731-37-5Relevant academic research and scientific papers
Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis
Park, Jin,Park, Sehoon,Jang, Gwang Seok,Kim, Ran Hui,Jung, Jaehoon,Woo, Sang Kook
supporting information, p. 9995 - 9998 (2021/10/06)
The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.
Photochemically-induced C-C bond formation between tertiary amines and nitrones
Itoh, Kennosuke,Kato, Ryo,Kinugawa, Daito,Kamiya, Hideaki,Kudo, Ryuki,Hasegawa, Masayuki,Fujii, Hideaki,Suga, Hiroyuki
supporting information, p. 8919 - 8924 (2015/08/24)
Photoexcited nitrones serve as excellent electron acceptors as well as radical acceptors in the presence of tertiary amines to give β-amino hydroxylamines via photochemically-induced direct sp3 C-H functionalization of the tertiary amines. The combined use of an organophotosensitizer and photoirradiation was highly effective in accelerating addition reactions. Several nitrones and tertiary amines were successfully utilized to give β-amino hydroxylamines in good yield. Highly regioselective generation of primary α-aminoalkyl radicals based on Lewis's stereoelectronic rule and diastereoselective addition reactions of primary α-aminoalkyl radicals with nitrones were successfully achieved. Furthermore, a highly diastereoselective reaction of an α-aminoalkyl radical with a chiral (E)-geometry-fixed α-alkoxycarbonylnitrone was performed.
Iron and manganese (III) - Porphyrins as new applicable catalysts for selective oxidation of imines with urea-hydrogen peroxide
Karami, Bahador,Montazerozohori, Morteza,Moghadam, Majid,Farahi, Mahnaz
, p. 275 - 277 (2008/02/09)
A variety of imines were oxidised with urea-hydrogen peroxide using iron(III) and manganese (III)- tetraphenylporphyrins [Fe(TPP)Cl], [Mn(TPP)Cl] and manganese (III)-octabromotetraphenyl porphyrin [Mn(TPPBr8)Cl] as catalysts. Experimental resul
Selective oxidation of N-alkyl imines to oxaziridines using UHP/maleic anhydride system
Damavandi, Jafar Asgarian,Karami, Bahador,Zolfigol, Mohammad Ali
, p. 933 - 934 (2007/10/03)
Several structurally differentiated N-alkyl imines were oxidized to their corresponding oxaziridines using UHP/maleic anhydride system. Oxidation reaction was performed under mild conditions and oxaziridines were obtained in good to excellent yields.
Synthesis of N-substituted N-nitrosohydroxylamines as inhibitors of mushroom tyrosinase
Shiino, Mitsuhiro,Watanabe, Yumi,Umezawa, Kazuo
, p. 1233 - 1240 (2007/10/03)
A series of N-substituted N-nitrosohydroxylamines including six new compounds were synthesized and examined for inhibition of mushroom tyrosinase. Corresponding hydroxylamines were reacted with n-butyl nitrite to give substituted nitrosohydroxylamines as their ammonium salt. The N-substituted hydroxylamines were prepared from the primary amines via the oxaziridine, or from the carbonyl compounds via the oxime. Most of the nitrosohydroxylamines tested inhibited mushroom tyrosinase. Among them, N-cyclopentyl-N-nitrosohydroxylamine exhibited the most potent activity (IC50=0.6 μM), as powerful as that of tropolone, one of the most powerful inhibitors. As removal of nitroso or hydroxyl moiety, the enzyme inhibitory activity was completely diminished. Both N-nitroso group and N-hydroxy group were suggested to be essential for the activity, probably by interacting with the copper ion at the active site of the enzyme. Lineweaver-Burk plotting showed that cupferron was a competitive inhibitor but that N-cyclopentyl-N-nitrosohydroxylamine was not.
