• Title/Summary/Keyword: 2-methoxy-1

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Synthesis of Nucleophilic Adducts of Thiols(II). Addition of Thioglycolic Acid to ${\beta}$-Nitrostyrene Derivatives (Thiol의 친핵성 첨가물의 합성 (제2보). ${\beta}$-nitrostyrene 유도체에 대한 Thioglycolic Acid의 친핵성 첨가반응)

  • Tae-Rin Kim;Tae-Sung Huh;In-Sup Han
    • Journal of the Korean Chemical Society
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    • v.25 no.6
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    • pp.390-393
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    • 1981
  • Eight new compounds were prepared by the addition reaction of thioglycolic acid to ${\beta}$-nitrostyrene and its derivatives. s-[2-Nitro-1-phenylethyl]-thioglycolic acid; s-[2-nitro-1-(p-methyl)phenylethyl]-thioglycolic acid; s-[2-nitro-1-(p-methoxy)phenylethyl]-thioglycolic acid; s-[2-nitro-1-(p-chloro)phenylethyl]-thioglycolic acid; s-[2-nitro-1-(p-bromo)phenylethyl]-thioglycolic acid; s-[2-nitro-1-(p-nitro)phenylethyl]-thioglycolic acid; s-[2-nitro-1-(3-methoxy-4-ethoxy)phenylethyl]-thioglycolic acid; s-[2-nitro-1-(3,4,5-trimethoxy)phenylethyl]-thioglycolic acid; The structure of these compound were identified by elemental analysis, UV, IR and NMR spectral data.

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Studies on the synthesis and antibacterial action of $N^4$-furoylsulfonamides ($N^4$-furoylsulfanamide류의 합성및 항균작용에 관한 연구)

  • 고현기
    • YAKHAK HOEJI
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    • v.13 no.2_3
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    • pp.62-66
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    • 1969
  • Ten new N$^{4}$-furoylsulfonamides were synthesized such as N$^{4}$-furoyl-N$^{1}$-(4,6-dimethyl-2-pyrimidinyl) sulfanilamide (I), N$^{4}$-furoylsulfanilamide (II), N$^{4}$-furoyl-N$^{1}$-(2,6-dimethoxy-4-pyrimidinyl) sulfanilamide (III), N$^{4}$-furoyl-N$^{1}$-(4-methyl-2-pyrimidinyl) sulfanilamide (IV), N$^{4}$-furoyl-N$^{1}$-(6-methoxy-3-pyridazinyl) sulfanilamide (V), N$^{4}$-furoyl-N$^{1}$-2-pyrimidinylsulfanilamide (VI), N$^{4}$-furoyl-N$^{1}$-(3,4-dimethyl-5-isoxazolyl) sulfanilamide (VII), N$^{4}$-furoyl-N$^{1}$-2-thiazoilysulfanilamide (VIII), N$^{4}$-furoyl-N$^{1}$-(5-methoxy-2-pyrimidinyl) sulfanilamide (IX) and N$^{4}$-furoyl-N$^{1}$-(2,6-dimethyl-4-pyrimidinyl) sulfanilamide (X). They were obtained by the action of N$^{1}$-(4,6-dimethyl-2-pyrimidinyl) sulfanilamide, N$^{1}$-(2,6-dimethoxy-4-pyrimidinyl) sulfanilamide, N$^{1}$-(4-methyl-2-pyrimidinyl) sulfanilamide, N$^{1}$-(6-methoxy-3-pyridazinyl) sulfanilamide, N-2-pyrimidinyl sulfanilamide, N$^{1}$-(3,4-dimethyl-5-isoxazolyl) sulfanilamide, N$^{1}$-2-(thiazolysulfanilamide), N$^{1}$-(5-methoxy-2-pyrimidinyl) sulfanilamide and N$^{1}$-(2,6-dimethyl-4-pyrimidinyl) sulfanilamide with furoyl chloride in 4% NaOH solution. Of the above ten compounds, N$^{4}$-furoylsulfathiazole exhibited a good antibacterial action against Staphylococeus aureus and Escherichia coli.

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Synthesis of Nucleophilic Adducts of Thiols (Ⅰ). Addition of Cysteine to $\beta$-Nitrostyrene Derivatives

  • Kim, Tae-Rin;Choi, Sung-Yong
    • Bulletin of the Korean Chemical Society
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    • v.2 no.4
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    • pp.125-129
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    • 1981
  • The addition reactions of cysteine without blocking amino and carboxyl groups to substituted and unsubstituted ${\beta}$-nitro-styrene derivatives were investigated. ${\beta}$-Nitrostyrene(1a), p-methyl-${\beta}$-nitrostyrene(1b), 3,4,5-trimethoxy-$[\beta}$ -nitrostyrene(1c), $[\varpi}$-3,4-methylenedioxy-${\beta}$ -nitrostyrene(1d), o-, m- and p-chloro-${\beta}$ -nitrostyrene (1e, 1f, 1g) and o-, m- and p-methoxy-${\beta}$-nitrostyrene (1h, 1i, 1j) easily undergo addition reactions with cysteine to form S-(2-nitro-1-phenylethyl)-L-cysteine(3a), S-[2-nitro-1-(p-methyl)phenyl-ethyl]-L-cysteine(3b), S-[2-nitro-1-(3',4',5'-trimethoxy) phenylethyl]-L-cysteine(3c), S-[2-nitro-1-($[\vatpi}$ -3',4'-methylenedioxy)phenylethyl]-L-cysteine(3d), S-[2-nitro-1-(o-chloro)phenylethyl]-L-cysteine(3e), S-[2-nitro-1-(m-chloro)-phenylethyl]-L-cysteine(3f), S-[2-nitro-1-(p-chloro)phenylethyl]-L-cysteine(3g), S-[2-nitro-1-(o-methoxy)phenylethyl]-L-cysteine(3h), S-[2-nitro-1-(m-methoxy)phenylethyl]-L-cysteine(3i) and S-[2-nitro-1-(p-methoxy)phenylethyl]-L-cysteine(3j), respectively. The structure of adducts were confirmed by means of UV-spectrum, IR-spectrum, molecular weight measurement and elemental analysis. The various factors effecting the yield of cysteine adducts to ${\beta}$-nitrostyrene derivatives were also studied.

A Study of Antibacterial Activity of Some Novel 8-Methoxy-4-methyl-quinoline Derivatives

  • Singh, Sheoraj;Kumar, Vikas;Kumar, Ashok;Sharma, Shalabh;Dua, Piyush
    • Bulletin of the Korean Chemical Society
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    • v.31 no.12
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    • pp.3605-3610
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    • 2010
  • In the present study, some quinoline derivatives have been synthesized like 8-methoxy-4-methyl-2-amino-(3'-chloro-2'-oxo-4'-substituted aryl-1'-azetidinyl)quinolines 8-12 and 8-methoxy-4-methyl-2-amino-(2'-substituted aryl-4'-oxo-1',3'-thiazolidin-3'-yl) quinolines 13-17 from 8-methoxy-4-methyl-2-(substituted arylidenyliminoamino)-quinolines 3-7. The structural assignments of these compounds were based on spectral (IR, $^1H$-NMR, Mass) and elemental (C, H, N) analysis. Further, these compounds were evaluated for antibacterial activity against various bacterial strains. Three compounds 10, 11 and 16 were found to exhibit potent antibacterial activity as compared to the standard drug amphicillin.

Synthesis of Nucleophilic Adducts of Thiols (Ⅳ). Addition of Glutathione to $\beta$-Nitrostyrene Derivatives

  • Kim, Tae-Rin;Choi, Sung-Yong;Choi, Won-Sik
    • Bulletin of the Korean Chemical Society
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    • v.4 no.2
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    • pp.92-95
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    • 1983
  • The addition products of glutathione to ${\beta}$ -nitrostyrene derivatives were synthesized. ${\beta}$ -Nitrostyrene (1a), p-methyl-${\beta}$-nitrostyrene (1b), 3,4,5-trimethoxy-${\beta}$-nitrostyrene (1c), o-, m- and p-chloro-${\beta}$-nitrostyrene (1e, 1f, 1g) and o-, m- and p-methoxy-${\beta}$-nitrostyrene (1h, 1i, 1j) undergo addition reactions with glutathione to form S-(2-nitro-1-phenylethyl)-L-glutathione (5a), S-[2-nitro-1-(p-methyl)phenylethyl]-L-glutatione (5b), S-[2-nitro-1-(3', 4', 5'-trimethoxy)phenylethyl]-L-glutathione (5c), S-[2-nitro-1-(o-chloro)phenylethyl]-L-glutathione (5e), S-[2-nitro-1-(m-choro)phenylethyl]-L-glutathione (5f), S-[2-nitro-1-(p-chloro)phenylethyl]-L-glutathione (5g), S-[2-nitro-x-(o-methoxy)-phenylethyl]-L-glutathion e(5h), S-[2-nitro-x-(m-methoxy)phenylethyl]-L-glutathion e (5i), and S-[2-nitro-1-(p-methoxy)phenylethy])-L-glutathione (5j), respectively. The structure of adducts were identified by UV and IR-spectra, molecular weight measurement, and elemental analysis.

Synthesis and Insecticidal effects of 2,2-bis(2-methoxy-5-chlorophenyl) 1,1,1-trichloroethane (2,2-bis(2-methoxy-5-chlorophenyl) 1,1,1-trichloroethane의 合成 과 殺蟲能에 관하여)

  • Lee, Dae-Soo;Kim, Jae-Hang;Choi, Won-Hyung;Choi, Young-Euion
    • Journal of the Korean Chemical Society
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    • v.10 no.4
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    • pp.149-152
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    • 1966
  • An insecticide was obtained by condensation of chloral hydrate with p-chloroanisole. The structure of the insecticide was found to be 2,2-bis(2-methoxy-5-chlorophenyl)1,1,1-trichloroethane(M.C.T.). The best conditions for this condensation reaction were as follows: 1) The sulfuric acid concentration: 93% 2) The mole ratio of sulfuric acid to p-chloroanisole: 8 3) The mole ratio of chloral hydrate to p-chloroanisole: 0.7 4) The reaction time and reaction temperature: 12 hrs and 25-30$^{\circ}C$ The insecticidal effects of M.C.T against the Citrus Red Mite and Chrysanthemum Aphid were five times as strong as D.D.T.

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Synthesis and Substituent Effects in Substituted Styryl 4-Methoxy-1-Naphthyl Ketones (다양한 치환기가 붙은 Styryl 4-Methoxy-1-Naphthyl Ketone의 합성과 치환기 효과에 관한 연구)

  • Thirunarayanan, G.;Ananthakrishna Nadar, P.
    • Journal of the Korean Chemical Society
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    • v.50 no.3
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    • pp.183-189
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    • 2006
  • A series of substituted styryl 4-methoxy-1-naphthyl ketones [(2E)-1-(4-methoxy-1-naphthyl)-3-phenyl-2-propen-1-ones] were synthesized using facile method of microwave assisted condensation reaction. The yield of chalcones is more than 90%. They are characterized by their physical constants, micro analysis, infrared (KBr, 4000-400 cm?1) and NMR both 1H and 13C spectral data. From infrared spectra, the s-cis and s-trans stretching vibrations of carbonyl group, from NMR spectra the ethylenic proton and carbon chemical shifts (ppm) are assigned. These spectral data are correlated with various Hammett substituent constants. From the results of statistical analysis the effect of substituents on CO, ? and ? proton and carbons are explained.

Concise Synthesis of (±)-Rhinacanthin A, Dehydro α-Lapachone, and β-Lapachone, and Pyranonaphthoquinone Derivatives

  • Wang, Xue;Chen, Ye;Lee, Yong-Rok
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.153-156
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    • 2011
  • A concise synthesis of (${\pm}$)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-$\alpha$-lapachone, followed by chemo- and regioselective reduction. Dehydro-$\alpha$-lapachone was also synthesized in two steps starting from 4-methoxy-1-naphthol by ethylenediamine diaetate (EDDA)-catalyzed benzopyran formation and a CAN-mediated oxidation reaction. $\beta$-Lapachone was synthesized in three steps from 4-methoxy-1-naphthol by benzopyran formation, catalytic hydrogenation, and Jones oxidation. As additional reactions, synthesis of pyranonaphthoquinone derivatives with the pyranokunthone B skeleton has been achieved in a single step from readily available 2-hydroxy-6-methoxy-1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4-naphthoquinone.

Nucleophilic Substitution Reaction of α-Methoxy-α-(trifluoromethyl)phenylacetyl Chloride in Alcohol-Water Mixtures

  • 구인선;이성인;안선경;양기열;이익춘
    • Bulletin of the Korean Chemical Society
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    • v.20 no.12
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    • pp.1451-1456
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    • 1999
  • Solvolyses of α-methoxy-α-(trifluoromethyl)phenylacetyl chloride in H₂O, D₂O, CH₃OD, 50% D₂O-CH₃OD, and in aqueous binary mixtures of acetone, dioxane, ethanol and methanol are investigated at 25.0℃. The Grunwald-Winstein plots of first-order rate constants for α-methoxy- α-(trifluoromethyl)phenylacetyl chloride with $Y_{Cl}$ show a dispersion phenomenon. Solvent nucleophilicity N has been shown to give considerable im-provement when it is added as an 1N term to the original Grunwald-Winstein for the solvolyses of α-methoxy- α-(trifluoromethyl)phenylacetyl chloride. The dispersions in the Grunwald-Winstein correlations in the present studies are caused by solvent nucleophilicity. The magnitude of l and m values associated with a change of solvent composition predicts the associative $S_N2$ transition state. The kinetic solvent isotope effects determined in deuterated water and methanol are consistent with the proposed mechanism of the general base catalyzed associative $S_N2$ or $S_AN$ mechanism for the of α-methoxy- α-(trifluoromethyl)phenylacetyl chloride.

Synthesis of Polybenzimidazole Containing Bulky Side Group (Bulky Side Group을 갖는 폴리벤즈이미다졸의 합성)

  • 안병현;김원호
    • 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.

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