<i>N</i>,<i>N</i>-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes

Xie, Sheng; Ramström, Olof; Yan, Mingdi

doi:10.1021/ol503655a

Cited by 31 publications

(16 citation statements)

References 46 publications

(36 reference statements)

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“…Enolates and enamines can also afford triazoles through a cycloaddition/elimination process. The amidation between electron‐deficient aryl azides and phenylacetaldehydes can be catalyzed by urea . Experimental data support a 1,3‐dipolar cycloaddition between DEU‐activated enols and electrophilic phenyl azides, followed by rearrangement of the triazoline intermediate.…”

Section: Reactions With Electrophilesmentioning

confidence: 86%

Recent Advances in Reactions of Azides

2017

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Azides are important intermediates in organic synthesis. They can function as precursors to form amines, amides, quinolones, pyridines, triazoles, amidines, indoles, and so on. Although there are some reviews about the applications of azides, few are concerned about their fundamental mechanisms. This review will focus on recent advances of azides based on three reactivity patterns, which may enlighten the further research.

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Section: Reactions With Electrophilesmentioning

confidence: 86%

Recent Advances in Reactions of Azides

2017

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“…TheFatoms lower the LUMO of the aryl azides,t hus giving PFAAs unique reactivity towards various coupling partners,f or example,e namines,t hioacids,a nd aldehydes. [14][15][16][17][18][19] Herein, we report that PFAAs undergo fast Staudinger reactions with aryl phosphines under ambient conditions to give stable iminophosphoranes ( Figure 1B). In addition, the reaction shows excellent bioothorgonality and was successfully applied to cell-surface labeling.…”

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confidence: 89%

Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

et al. 2017

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We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, occurring readily under ambient conditions. A rate constant as high as 18 M−1 s−1 was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD3CN/D2O. In addition, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. The PFAA-Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannose and galactose were successfully transformed into cell surface glycans and efficiently labeled with phosphine-derivatized fluorescent bovine serum albumin.

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“…This unique reactivity of perfluoroaryl azides is due to their highly electron-deficient nature, which allows these electrophilically activated azides to undergo cycloaddition with enamines at room temperature without any catalysts (29,30), and also with other dipolarophiles and nucleophiles (31)(32)(33). Ciprofloxacin is sparingly soluble in common organic solvents.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of theranostic antibiotic nanodrugs that display enhanced antibacterial activity and luminescence

Xie

Manuguri

Proietti

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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We report the modular formulation of ciprofloxacin-based pure theranostic nanodrugs that display enhanced antibacterial activities, as well as aggregation-induced emission (AIE) enhancement that was successfully used to image bacteria. The drug derivatives, consisting of ciprofloxacin, a perfluoroaryl ring, and a phenyl ring linked by an amidine bond, were efficiently synthesized by a straightforward protocol from a perfluoroaryl azide, ciprofloxacin, and an aldehyde in acetone at room temperature. These compounds are propeller-shaped, and upon precipitation into water, readily assembled into stable nanoaggregates that transformed ciprofloxacin derivatives into AIE-active luminogens. The nanoaggregates displayed increased luminescence and were successfully used to image bacteria. In addition, these nanodrugs showed enhanced antibacterial activities, lowering the minimum inhibitory concentration (MIC) by more than one order of magnitude against both sensitive and resistant Escherichia coli. The study represents a strategy in the design and development of pure theranostic nanodrugs for combating drug-resistant bacterial infections.nanodrugs | aggregation-induced emission | fluoroquinolones

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N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes

Cited by 31 publications

References 46 publications

Recent Advances in Reactions of Azides

Recent Advances in Reactions of Azides

Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

Design and synthesis of theranostic antibiotic nanodrugs that display enhanced antibacterial activity and luminescence

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