The Gabriel synthesis of benzylamine: An undergraduate organic experiment

Nigh, W. G.

doi:10.1021/ed052p670

Cited by 8 publications

(5 citation statements)

References 1 publication

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“…It was aimed at synthesizing polymers of different molecular weight by varying the amount of monomer and the reaction time. The synthesis process of amine end-functionalized polystyrene (PS-NH 2 ) is shown in Scheme 1, which is known as the Gabriel synthesis [41]. Specifically, the primary chloride group in compound 1 reacted with potassium phthalimide to give compound 2.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polystyrene-Coated Superparamagnetic and Ferromagnetic Cobalt Nanoparticles

et al. 2018

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Polystyrene-coated cobalt nanoparticles (NPs) were synthesized through a dual-stage thermolysis of cobalt carbonyl (Co2(CO)8). The amine end-functionalized polystyrene surfactants with varying molecular weight were prepared via atom-transfer radical polymerization technique. By changing the concentration of these polymeric surfactants, Co NPs with different size, size distribution, and magnetic properties were obtained. Transmission electron microscopy characterization showed that the size of Co NPs stabilized with lower molecular weight polystyrene surfactants (Mn = 2300 g/mol) varied from 12–22 nm, while the size of Co NPs coated with polystyrene of middle (Mn = 4500 g/mol) and higher molecular weight (Mn = 10,500 g/mol) showed little change around 20 nm. Magnetic measurements revealed that the small cobalt particles were superparamagnetic, while larger particles were ferromagnetic and self-assembled into 1-D chain structures. Thermogravimetric analysis revealed that the grafting density of polystyrene with lower molecular weight is high. To the best of our knowledge, this is the first study to obtain both superparamagnetic and ferromagnetic Co NPs by changing the molecular weight and concentration of polystyrene through the dual-stage decomposition method.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Polystyrene-Coated Superparamagnetic and Ferromagnetic Cobalt Nanoparticles

et al. 2018

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“…The ester group of naphthoate 3 was sequentially converted to alcohol 4 (LAH/THF, 98%) and subsequently to chloride 5 (CCl 4 /PPH 3 , 78%) . Conversion of chloride 5 to aminomethylene compound 7 via compound 6 was accomplished via Gabriel reaction through two steps (potassium phthalimide, and then N 2 H 4 /H 2 O) with 77% overall yield. Aminomethylene compound 7 could be a versatile platform compound to introduce diverse amino substituents to the 1‐ and 12‐positions of the perylenequinone core ( 10 ) by N ‐alkylation or N ‐acylation, leading to structurally diverse amino‐functionalized calphostin derivatives for investigation of structure–activity relationships.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Amino‐Functionalized Calphostin Analogs as Potent and Selective Inhibitors of Protein Kinase C (PKC)

Kim¹,

Song²,

Kim

et al. 2016

Bulletin Korean Chem Soc

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As potential protein kinase C (PKC) inhibitors and photodynamic agents, the novel amino-functionalized calphostin analog 1,12-bis((benzoyl-amino)methyl)-3,10-perylenequinone was successfully prepared by dimerization of the key intermediate 3-(benzoylamino)methyl-1,2-naphthoquinone (9), which was synthesized by an efficient and relatively short synthetic sequence (eight steps) with satisfactory overall yield. The naturally occurring form of perylenequinone 12 was prepared by consecutive methylation and demethylation reactions. In our synthetic strategy, it was beneficial that the amino functionality of 1,2naphthoquinone 9 could be easily introduced at an early synthetic stage and subsequently dimerized to prepare various potentially bioactive perylenequinones. Scheme 3. Preparation of target compound, namely the naturally occurring form of amino-functionalized perylenequinone (12), from 1,2naphthoquinone (9). (a) TFA, 0 C; (b) 10% FeCl 3 , CH 3 CN, rt; (c) TBAF, THF, MeI, rt; (d) MgI 2 , THF, rt. Scheme 4. Dimerization mechanism proposed by Merlic et al. 7

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“…[53][54][55][56][57][58][59][60] To obtain primary alkyl halide, starting material was chosen as 2,5-dibromotoluene as it can readily react with N-bromosuccinimide (NBS) to afford allylic bromination of methyl group of toluene in the presence of peroxide. Suzuki coupling reaction providing more straightforward access to obtain polymer with changeable sequence ratio between amino functional and PEG monomers was used to adjust the higher contribution of amino monomer than PEG macromonomer to PPP structure.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and targeted cell imaging applications of poly(p-phenylene)s with amino and poly(ethylene glycol) substituents

et al. 2015

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A novel approach for bioconjugation associated with fluorescent conjugated polymer is demonstrated. For this purpose, a conjugated polymer, poly(p-phenylene) (PPP), with lateral substituents, namely primary amino groups and poly(ethylene glycol) (PEG) chains, as potential building block for polymer bioconjugates was synthesized and characterized. The synthesis was achieved through Suzuki polycondensation reaction in the presence of Pd(PPh3)4 catalyst by using independently prepared PEG and amino functional dibromo benzenes in conjunction with benzene diboronic acid. For the evaluation of the bioactive PPP labeled with folic acid (FA) as a potential targeted cell imaging probe, HeLa and A549 cancer cells were used. Cytotoxicity assay showed that the polymer was not toxic to the both cells. Additionally, the fluorescence images showed that, depending on the level of the FA receptors on the cell surfaces, the fluorescent intensity in HeLa cells was obviously higher than A549 cells when treated with FA conjugated PPP-NH2-g-PEG polymer. The resulting FA/PPP-NH2-g-PEG conjugate was successfully used as bioconjugate for targeting and specifically imaging of FA receptor positive HeLa human cervices cancer cells.

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The Gabriel synthesis of benzylamine: An undergraduate organic experiment

Cited by 8 publications

References 1 publication

Synthesis of Polystyrene-Coated Superparamagnetic and Ferromagnetic Cobalt Nanoparticles

Synthesis of Polystyrene-Coated Superparamagnetic and Ferromagnetic Cobalt Nanoparticles

Total Synthesis of Amino‐Functionalized Calphostin Analogs as Potent and Selective Inhibitors of Protein Kinase C (PKC)

Synthesis, characterization and targeted cell imaging applications of poly(p-phenylene)s with amino and poly(ethylene glycol) substituents

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