• Journal of the Korean Magnetic Resonance Society
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• v.22 no.4
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• pp.115-118
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• 2018

Dipyrromethane 2 functionalized with 3-chloropropyl group on the meso carbon undergoes an unusual intramolecular electrophilic aromatic substitution reaction in the presence of $NaN_3$ instead of a simple nucleophilic substitution reaction. As a result, a new chiral dipyrromethane 1 was synthesized. In this reaction, the ${\beta}$-carbon of the pyrrole ring functions as a nucleophile while the carbon next to the chlorine atom acts as an electrophile. Interestingly, this reaction progresses even in the absence of an acid catalyst. Compound 1 was fully characterized by $^1H-^1H$ and $^1H-^{13}C$ COSY NMR spectroscopic analyses and the high resolution EI mass spectrometry.

• YAKHAK HOEJI
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• v.33 no.5
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• pp.273-279
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• 1989

2,3-Dichloro-1,4-naphthoquinone was reacted with o-fluoroaniline, p-sulfadiazine, p-acetoanline, N,N-dimethyl-1,4-phenylenediamine as a nucleophilic substitution to form 2-chloro-3-(N-arylamino)-1,4-naphthoquinones (1.-6.) in good yield. 2,3-Dibromo-1,4-naphthoquinone was also reacted with o-fluoroaniline, m-aminobenzoic acid, m-chloroaniline, morpholine, p-acetoaniline, N,N-dimethyl-1,4-phenylenediamine as a nucleophilic substitution to give 2-bromo-3-(N-arylamino)-1,4-naphthoquinones (7.-12.). These new compounds are expected to have a biological activities such as anticoagulant, cytotoxic.

• Bulletin of the Korean Chemical Society
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• v.26 no.4
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• pp.668-670
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• 2005

• Bulletin of the Korean Chemical Society
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• v.30 no.10
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• pp.2294-2298
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• 2009

In present work an attempt was made to synthesize various analogues of levofloxacin by introducing new functionality at carboxylic group position via nucleophilic substitution reaction. For this purpose the carboxylic group at C-6 was esterified and later subjected to nucleophilic attack at the carbonyl carbon by various aromatic amines. Structure of the analogues was confirmed by different techniques i.e. IR, $^1H$ NMR and mass spectrometry. The antibacterial activity of the derivatives was also assessed and compared with the parent against a series of Gram-positive and Gramnegative bacteria. A synergistic as well as antagonistic behavior was observed in these derivatives. Additionally unlike levofloxacin, the derivatives were also found to modulate oxidative burst response of phagocytes exhibiting moderate to significant inhibitory activity.

• Bulletin of the Korean Chemical Society
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• v.12 no.6
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• pp.658-661
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• 1991

The gas-phase nucleophilic substitution reaction of pentafluoroanisole with $OH^-$ and ${NH_2}^-$ nucleophiles have been studied theoretically using the AM1 method. Three reaction channels, $S_N2$, IPSO and $S_NAr$ (scheme 1), are all very exothermic so that all are accessible despite the varying central energy barriers which are much lower than the reactants level. In the IPSO and $S_NAr$ channels, the reactants form directly a stable ,${\sigma}$-anion complex which proceeds to form a proton transfer complex via a transition barrier corresponding to a loose ${\pi}$-type complex with the F-(or ${OCH_3}^-$) leaving group. Due to a greater number of probable reaction sites available for $S_NAr$ compared to the other two processes, the $S_NAr$ channel is favored as experimentally observed.

• YAKHAK HOEJI
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• v.39 no.2
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• pp.118-130
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• 1995

Aliphatic & aromatic compounds with two nucleophilic functional groups which were chosen as nucleophiles reacted with 2,3-dichloro-1,4-naphthoquinone as a substrate to give cyclized products by nucleophilic vinyl substitution. And the trends in the syntheses of the heterocyclic compounds was studied and expounded. Besides, the biological activities of the products, especially activity as an agricultural chemical, were examined. Moreover 5-aminomethyl-2-pyrrolidinone was synthesized for the purpose of forming a polynuclear heterocyclic compound containing a similar structure of azasteroid. However only one chlorine of 2,3-dichloro-1,4-naphthoquinone was replaced by an amino group of pyrrolidinone and cyclization did not take place.

• Polymer(Korea)
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• v.25 no.6
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• pp.796-802
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• 2001

Novel monomer for polybenzimidazole was prepared and polymerized via aromatic nucleophilic substitution reaction. Thus, N-(4-fluorobenzoyl)-4-methoxy-N'-naphthyl-1,2-phenylenediamine was synthesized from the reaction of 4-methoxy-N-naphthyl-1,2-phenylenediamine and 4-fluorobenzoyl chloride. N-(4-fluorobenzoyl)-4-methoxy-N'-naphthyl-1,2-phenylenediamine was converted to 2-(4-fluorobenzoyl)-5-hydroxy-1-naphthylbenzimidazole by ring closure and demethylation reaction. Polymerization was done in N-cyclohexyl-2-pyrrolidinone (CHP) containing potassium car bonate. The resulting polymer was soluble in N-methyl-2-pyrrolidinone (NMP) and had inherent viscosity of 0.38 dL/g (NMP at $30^{\circ}C$). The glass transition temperature ($T_g$ ) of the polybenzimidazole was $270^{\circ}C$. The thermogravimetric analysis (TGA) thermograms of this polymer showed 5% weight losses at $550^{\circ}C$ in nitrogen and at $540^{\circ}C$ in air.

• The Korean Journal of Pesticide Science
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• v.8 no.4
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• pp.258-264
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• 2004

The pyrazole family was discovered as effective insecticides/acaricides, and fenpyroximate and tebufenpyrad were introduced in the market. In this study, new series of pyrazole oxime ethers were designed and synthesized. The pyrazolone 1 was prepared by the condensation of ethyl acetoacetate with methylhydrazine, and then subsequently subjected to the Vilsmeier-Haack chloroformylation yielding 4-formyl-5-chloro-pyrazole 2. The nucleophilic aromatic substitution of 2 generally allowed the introduction of a wide range of heterocycles into the pyrazole ring. The resulting pyrazole aldehydes 3a-i were readily converted to the corresponding pyrazole oxime derivatives 4a-i, and subsequently to 5-substituted pyrazole oxime ether derivatives 6a-i. The screening assay results clearly show that the activities of 6d were comparable to those of fenpyroximate (6a) against BPH, DBM, and TSSM. It indicates that 6d has a potential to be developed as an insecticidal agent.

• Bulletin of the Korean Chemical Society
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• v.21 no.9
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• pp.896-900
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• 2000

A study was done on the synthesis of new poly(arylene ether)s and poly(arylenesulfide) with rigid benzoxazole pendants using nucleophilic aromatic substitution reaction. As a new aromatic monomer, 1,4-bis(2-benzox-azolyl)-2,5-difluorobenzene [I] w as synthesized in three steps starting from 1,4-dibromo-2,5-difluorobenzene. A model reaction of difluoro monomer [I] with two equivalents of m-cresol or thiophenol in a typical ether con-densation reaction conditions gave very high yields ( > 93%) of the desired disubstituted product, suggesting the feasibility of polymer formation in these reaction system. Monomer[I] was polymerized with bisphenols and bisbenzenethiol in NMP using K2CO3 as base. The molecular weight of the resulting polymers, however,seemed relatively low according to their solution viscosity values ( ηinh = 0.15-0.29 dL/g). The poly(arylene ether)s were soluble in several common organic solvents including chloroform, pyridine and N,N'-dimethylfor-mamide. The poly(arylene sulfide) was, however, ony soluble in strong acids like sulfuric acid and trifluoro-acetic acid. The glass transition temperatures were found to be 175-215 $^{\circ}C.$ These polymers were stable up to 380-420 $^{\circ}C$ in both nitrogen and air, as determined by the temperature that a significant weight loss began to appear on TGA.

• Proceedings of the Korean Powder Metallurgy Institute Conference
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• 2006.09a
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• pp.487-488
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• 2006

Novel bisphenol-based wholly aromatic poly(ether sulfone-ketone) copolymer containing pendant sulfonate groups were prepared by direct aromatic nucleophilic substitution polycondensation of 4,4-difluorobenzophenone, 2,2'-disodiumsulfonyl-4,4'-fluorophenylsulfone (40mole% of bisphenol A) and bisphenol A. Polymerization proceeded quantitatively to high molecular weight in N-methyl-2-pyrrolidinone at $180^{\circ}C$. Organic-inorganic composite membranes were obtained by mixing organic polymers with hydrophilic $SiO_2$ (ca. 20nm) obtained by sol-gel process. The polymer and a series of composite membranes were studied by FT-IR, $^1HNMR$, differential scanning calorimetry (DSC) and thermal stability. The proton conductivity as a function of temperature decreased as $SiO_2$ content increased, but methanol permeability decreased. The nano composite membranes were found to posse all requisite properties; Ion exchange capacity (1.2meq./g), glass transition temperatures $(164-183\;^{\circ}C)$, and low affinity towards methanol $(4.63-1.08{\times}10^{-7}\;cm^2/S)$.