Catalyst-Free Microwave-Assisted Amination of 2-Chloro-5-nitrobenzoic Acid

Müller, Christian

doi:10.1021/jo070731i

Cited by 28 publications

(18 citation statements)

References 47 publications

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“…The syntheses of compounds 5, 7-10, 15-20, 22-25, 27-29, 31-43, 46, and 49 have previously been described. 32,34,35 21,26,30,47,50, and 53-55, whose syntheses had previously been described by classical methods, 35,[39][40][41][42][43][44][45][46][47][48] as well as the new compounds 11,44,45,48,51,52, and 56-60 were obtained in analogy to a new method recently developed by our group applying a simple and efficient microwave-assisted Ullmann reaction (Scheme 1). 49 Our experiments showed that a wide variety of amines (aliphatic and aromatic) including highly electron-deficient ones could be smoothly coupled with anthraquinone halide derivatives 6.…”

Section: Resultsmentioning

confidence: 99%

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Development of Potent and Selective Inhibitors of ecto-5′-Nucleotidase Based on an Anthraquinone Scaffold

et al. 2010

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ecto-5'-Nucleotidase (eN, CD73) plays a major role in controlling extracellular adenosine levels. eN inhibitors have potential as novel drugs, for example, for the treatment of cancer. In the present study, we synthesized and investigated a series of 55 anthraquinone derivatives as potential inhibitors of eN, 11 of which are novel compounds and another 11 of which had previously been described but have now been synthesized by an improved method. We identified several potent inhibitors of rat eN. The most potent compounds were 1-amino-4-[4-fluoro-2-carboxyphenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (45, PSB-0952, K(i) = 260 nM) and 1-amino-4-[2-anthracenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (52, PSB-0963, 150 nM), with 52 being the most potent eN inhibitor described to date. Selected compounds were further characterized and found to exhibit a competitive mechanism of inhibition. Investigations of ecto-nucleoside triphosphate diphosphohydrolases (NTPDases) and the P2Y receptor subtypes P2Y(2), P2Y(4), P2Y(6), and P2Y(12) showed that compound 45 exhibited the highest degree of selectivity (>150-fold).

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Section: Resultsmentioning

confidence: 99%

“…The syntheses of compounds 5, 7-10, 15-20, 22-25, 27-29, 31-43, 46, 49, 50, 53, 62, and 63 were previously described. 32,33,35,48,49 All other compounds were newly prepared in analogy to the described method. 49 General Procedure.…”

Section: Methodsmentioning

confidence: 99%

Development of Potent and Selective Inhibitors of ecto-5′-Nucleotidase Based on an Anthraquinone Scaffold

et al. 2010

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“…There were three aromatic proton signals also observed in the NMR spectrum of functionalized PMMA. The NMR signal at 7.134 ppm was observed for H d of aromatic ring while signals at 7.829 and 8.210 ppm were observed for H e and H f of aromatic ring . The shifting in the δ values of these signals was observed due to presence of highly electronegative moieties (electron withdrawing group) in neighbor of these protons.…”

Section: Resultsmentioning

confidence: 95%

Impact of vanadium‐, sulfur‐, and dysprosium‐doped zinc oxide nanoparticles on various properties of PVDF/functionalized‐PMMA blend nanocomposites: Structural, optical, and morphological studies

Singh

Madhav

Yadav³

et al. 2018

J of Applied Polymer Sci

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The polymeric blend was fabricated with crystalline poly(vinylidene fluoride) (PVDF)/amorphous functionalized-poly (methyl methacrylate) (PMMA) in 70/30 w/w ratio by chemical mixing method. Functionalization of PMMA was achieved with 2-amino-5-nitrobenzoic acid. The prepared polymer blend was used as a matrix to synthesize nanocomposites with undoped/doped zinc oxide (ZnO) nanoparticles. Doping in ZnO was achieved with vanadium, sulfur, and dysprosium elements as a dopant. The structural, optical, electronic, and morphological properties of undoped/doped nanosized ZnO and blended nanocomposites were accessed through sophisticated analytical techniques, that is, Fourier transform infrared (FTIR), ultraviolet-visible (UV-vis), UV-vis-diffuse reflectance spectra, nuclear magnetic resonance, fluorescence spectroscopy, X-ray diffraction (XRD), transmission electron microscopy, and scanning electron microscopy. The FTIR band at 1165-1176 cm −1 in functionalized-PMMA indicate the formation of aliphatic C-N bond along with aromatic 1 H chemical shift (δ) at 7.134, 7.829 and 8.210 ppm confirm the successfully functionalization of PMMA. The prominent XRD peak at 2θ = 20.8 in nanocomposites shown improvement in β-phase of PVDF. The results show that Dy doped ZnO nanoparticles create remarkable effect on various properties of nanocomposites.

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“…The precipitated solid was filtered off, washed with distilled water (3×20 mL) and re-crystallised from ethanol/water to give the desired product with the yields listed in Tables 2 and 3. 13 …”

Section: Amination Of 2-chloro-5-nitrobenzoic Acid In Superheated Water;mentioning

confidence: 99%

Metal Catalyst-Free Amination of 2-chloro-5-nitrobenzoic Acid in Superheated Water

Lan

Xia

et al. 2012

Journal of Chemical Research

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A series of N-arylanthranilic acid derivatives were synthesised by amination of 2-chloro-5-nitrobenzoic acid with various arylamine in superheated water with potassium carbonate as base. Good yields were achieved within 2−3 h at 150−190 °C. The results indicated that this metal catalyst-free method is a simple, environmentally-friendly and efficient synthesis of N-phenylanthranilic acid derivatives. Furthermore, it will work with an alkylamine and phenol.

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Catalyst-Free Microwave-Assisted Amination of 2-Chloro-5-nitrobenzoic Acid

Cited by 28 publications

References 47 publications

Development of Potent and Selective Inhibitors of ecto-5′-Nucleotidase Based on an Anthraquinone Scaffold

Development of Potent and Selective Inhibitors of ecto-5′-Nucleotidase Based on an Anthraquinone Scaffold

Impact of vanadium‐, sulfur‐, and dysprosium‐doped zinc oxide nanoparticles on various properties of PVDF/functionalized‐PMMA blend nanocomposites: Structural, optical, and morphological studies

Metal Catalyst-Free Amination of 2-chloro-5-nitrobenzoic Acid in Superheated Water

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