Fluorinated organic azides – their preparation and synthetic application

Tomaszewska, Joanna; Koroniak-Szejn, Katarzyna; Koroniak, Henryk

doi:10.24820/ark.5550190.p009.771

Cited by 3 publications

(3 citation statements)

References 51 publications

(80 reference statements)

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“…Thin-layer chromatography (TLC) and an MS analysis of the reduction of 1b with sodium borohydride provides evidence for the formation of p-amino benzyl alcohol, the product of water addition to the imine of p-quinone methide. The addition of sodium borohydride/copper (II) sulfate, a mixture known to reduce azides to amines [28], to 1c and 2c produces 89 and 92% N 2 O, respectively (Table 2). These results support Scheme 1 and suggest a reduction of the nitro and azide groups to the amine followed by decomposition to the Piloty's acid derivative.…”

Section: Compoundmentioning

confidence: 99%

Para-Substituted O-Benzyl Sulfohydroxamic Acid Derivatives as Redox-Triggered Nitroxyl (HNO) Sources

et al. 2022

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Nitroxyl shows a unique biological profile compared to the gasotransmitters nitric oxide and hydrogen sulfide. Nitroxyl reacts with thiols as an electrophile, and this redox chemistry mediates much of its biological chemistry. This reactivity necessitates the use of donors to study nitroxyl’s chemistry and biology. The preparation and evaluation of a small library of new redox-triggered nitroxyl sources is described. The condensation of sulfonyl chlorides and properly substituted O-benzyl hydroxylamines produced O-benzyl-substituted sulfohydroxamic acid derivatives with a 27–79% yield and with good purity. These compounds were designed to produce nitroxyl through a 1, 6 elimination upon oxidation or reduction via a Piloty’s acid derivative. Gas chromatographic headspace analysis of nitrous oxide, the dimerization and dehydration product of nitroxyl, provides evidence for nitroxyl formation. The reduction of derivatives containing nitro and azide groups generated nitrous oxide with a 25–92% yield, providing evidence of nitroxyl formation. The oxidation of a boronate-containing derivative produced nitrous oxide with a 23% yield. These results support the proposed mechanism of nitroxyl formation upon reduction/oxidation via a 1, 6 elimination and Piloty’s acid. These compounds hold promise as tools for understanding nitroxyl’s role in redox biology.

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Section: Compoundmentioning

confidence: 99%

Para-Substituted O-Benzyl Sulfohydroxamic Acid Derivatives as Redox-Triggered Nitroxyl (HNO) Sources

et al. 2022

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“…Evaporating the solvent by rotary evaporator to furnish hepta-Oacetyl-6'-O-azido-sucrose [6] (3.54g, 71%) as pure white crystals after recrystallization with ethyl alcohol. (Kamijo et al, 2015;Tomaszewska et al, 2017;Hosoya et al, 2019).…”

Section: Azidation Of Hepta-o-acetyl-6'-o-tosyl-sucrose [6]mentioning

confidence: 99%

New bio-amphiphilic structures of sucrose via amides linkages

Salman¹

2019

ijrps

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A series of four new derivatives of sucrose have been synthesized using the straightforward methodology in order to give a mono substituted analogs of sucrose at C −6 ′ of fructose moiety. The synthesis was started from the reaction of sucrose with tert-butylchlorodiphenylsilane, which is able to react with an only less steric hindrance hydroxyl group at C −6 ′ due to its bulky structure. The other hydroxyl groups were acetylated by the reaction with acetic anhydride in pyridine. Then free the hydroxyl group at C −6 ′ again by the treatment with t-butylammonium luoride in THF. The later was activated by conversion to a good leaving group via tosylation, followed by functionalized via azidation to give the precursor of the target series hepta-O-acetyl-6'-azido-sucrose. The precursor was coupled with four alkyl halides (C 12 , C 8−4 , C 14 , C 10−8 ) via Staudinger reaction to produced the target structure after deacetylating. The purity and chemical structure of the synthesized compound was con irmed by CHN elemental analysis, high-resolution mass and 1 H, 13 C NMR spectroscopy.

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“…The resulting organic azides are versatile compounds that provide an excellent starting point for the synthetic preparation of amines and the corresponding derivatives, nitrogen heterocycles, such as the extensively studied 1,2,3-triazoles, etc. 26,27 In our previous research, 28 we showed that HHDHs can be employed in the kinetic resolution of fluorinated aromatic epoxides, giving access to the corresponding enantioenriched or enantiopure fluorinated β-azido alcohols of synthetic relevance. Although HHDHs are potent biocatalysts, lower productivity on the preparative scale occurs as a result of chemical side reactions in the system.…”

Section: Introductionmentioning

confidence: 99%