An electrochemical alternative strategy to the synthesis of β-lactams

Sotgiu, Giovanni; Chiarotto, Isabella; Feroci, Marta; Orsini, Monica; Rossi, Leucio; Inesi, Achille

doi:10.1016/j.electacta.2008.05.054

Cited by 29 publications

(14 citation statements)

References 60 publications

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“…The peak at TIC RT = 2.56 min, present also in ACN electrolyzed solutions (Figures 4a-c), was due to DMF because of its presence in the gel dividing the anodic and cathodic compartments. [22]…”

Section: Theophylline Electro-oxidation In Watermentioning

confidence: 99%

Electrochemical Oxidation of Theophylline in Organic Solvents: HPLC‐PDA‐ESI‐MS/MS Analysis of the Oxidation Products

et al. 2019

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The electrochemical oxidation of theophylline was investigated by controlled potential electrolysis in two different organic solvents and in water for comparison. The anodic oxidation was monitored by cyclic voltammetry in situ and UV‐Vis spectrophotometry ex situ and the final electrolyzed solutions were analyzed by tandem mass spectrometry after chromatographic separation with an HPLC‐PDA‐ESI‐MS/MS system. The main oxidation products evidenced as the main diode array chromatographic peaks were tentatively assigned to dimeric forms of theophylline, two of which have never been reported before, on the base of retention time, UV‐Vis spectrum, m/z ratio in both positive and negative ESI modes and fragmentation pattern. Two chemical paths following the primary mono‐electronic anodic oxidation of theophylline to the final evidenced oxidation products have been proposed.

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Section: Theophylline Electro-oxidation In Watermentioning

confidence: 99%

Electrochemical Oxidation of Theophylline in Organic Solvents: HPLC‐PDA‐ESI‐MS/MS Analysis of the Oxidation Products

et al. 2019

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“…The electrochemically induced cyclization of bromoamides to β‐lactams also occurred in room‐temperature ionic liquids (RTILs) (Scheme ) . The eco‐friendly process avoided the use of volatile organic solvents (VOCs) and supporting electrolytes, affording the desired β‐lactams in good to elevated yields via C3−C4 bond formation.…”

Section: Intramolecular α‐Alkylation Of α‐Haloamides: Syntheses Of β‐mentioning

confidence: 99%

“…[76] The electrochemically induced cyclization of bromoamides to β-lactams also occurred in room-temperature ionic liquids (RTILs) (Scheme 48). [77] The eco-friendly process avoided the use of volatile organic solvents (VOCs) and supporting electrolytes, affording the desired β-lactams in good to elevated yields via C3À C4 bond formation. The reaction protocol entailed the addition of the haloamide A to an electrolyzed solution of probases (PB) azobenzene or tetraethyl ethenetetracarboxylate in the RTIL (1-butyl-3-methylimidazolium exafluorophospate).…”

Section: Intramolecular α-Alkylation Of α-Haloamides: Syntheses Of β-mentioning

confidence: 99%

The Fascinating Chemistry of α‐Haloamides

et al. 2020

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The aim of this review is to highlight the rich chemistry of α‐haloamides originally mainly used to discover new C−N, C−O and C−S bond forming reactions, and later widely employed in C−C cross‐coupling reactions with C(sp3), C(sp2) and C(sp) coupling partners. Radical‐mediated transformations of α‐haloamides bearing a suitable located unsaturated bond has proven to be a straightforward alternative to access diverse cyclic compounds by means of either radical initiators, transition metal redox catalysis or visible light photoredox catalysis. On the other hand, cycloadditions with α‐halohydroxamate‐based azaoxyallyl cations have garnered significant attention. Moreover, in view of the important role in life and materials science of difluoroalkylated compounds, a wide range of catalysts has been developed for the efficient incorporation of difluoroacetamido moieties into activated as well as unactivated substrates.

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“…a room temperature ionic liquid, RTIL) without any use of bases or reducing agents and in total absence of classic organic solvents (VOCs) and was extended to other 1,3-dialkylimidazolium salts [12][13][14].…”

Section: Introductionmentioning

confidence: 99%