• Title/Summary/Keyword: imine

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Synthesis of Novel Taxol Analogues with Heterocylclic Amino Moieties (헤테로환성 아민기를 갖는 신규 택솔유도체의 합성)

  • 박해일
    • YAKHAK HOEJI
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    • v.45 no.4
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    • pp.321-327
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    • 2001
  • The synthesis of novel taxol analogues with an amine moiety at the 7- and 10-positions to examine the BBB penetration was described. The analogues were synthesized from 2'-O-(tert-butyldim-ethylsilyl)taxol and 2'-0-(tert-butyldimethylsilyl) -7-O-(triethylsilyl)-10-deacetyltaxol, the key intermediates, in 2 steps via the esterification with heterocyclic amino acids and the subsequent desilylation reaction.

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Synthesis of Novel H8-Binaphthol-based Chiral Receptors and Their Applications in Enantioselective Recognition of 1,2-Amino alcohols and Chirality Conversion of L-Amino acids to D-Amino acids

  • Jung, Hye-In;Nandhakumar, Raju;Yoon, Hoe-Jin;Lee, Sang-Gi;Kim, Kwan-Mook
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1289-1294
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    • 2010
  • Novel $H_8$-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities ($K_R/K_S$ = 9.8 ~ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a ($K_R/K_S$ = 1.8 ~ 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3 ~ 10.1) is superior to 2a (D/L ratio: 4.0 ~ 8.7).

The Chirality Conversion Reagent for Amino Acids Based on Salicyl Aldehyde

  • Yoon, Hoe-Jin;Jung, Hein;Ahn, Yun-Soo;Nandhakumar, Raju;Kim, Jun-Soo;Kim, Kwan-Mook
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1715-1718
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    • 2012
  • 2-Hydroxy-6-(1-(3-phenylurylphenyl)ethoxy)-benzaldehyde ($\mathbf{2}$) has been synthesized in racemic form from 1,3-Dihydroxybenzene via formylation and reaction with 3-phenyluryl-methylbenzylbromide. The optically pure form of $\mathbf{2}$ was separated by normal silica column chromatography from the imine diastreomer which was obtained by the reaction of racemic mixture of $\mathbf{2}$ with optically pure leucinol. The absolute configuration of the separated enantiomer of $\mathbf{2}$ was decided from the energy calculation of the corresponding imine diastereomers. The activity of $\mathbf{2}$ as a chirality conversion reagent (CCR) for amino acids was determined by $^1H$ NMR analysis. The efficiency of $\mathbf{2}$ is not better than the previous CCRs based on binaththol. Compound $\mathbf{2}$, however, has lower molecular weight compared to other CCRs. This work demonstrates that asymmetric carbon can control the selectivity of amino acids.

The Mechanism in the Photolysis of 5-Phenyl-tetrazole Derivatives (5-Phenyl-tetrazole의 光分解反應과 그 메카니즘에 관한 硏究)

  • Chae, Young-Bok;Chang, Kyung-Soo;Kim, Sung-Soo
    • Journal of the Korean Chemical Society
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    • v.11 no.3
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    • pp.85-88
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    • 1967
  • The main object of this experiment is to provide a systematic approach to the reaction mechanism in the photolysis of 5-phenyl-1,2,3,4-tetrazole during which the formation of C-phenyl-nitrile-imine of 1.3-dipole was expected. So the occurrence of 1,3-dipole-addition was examined but not observed despite the formation of nitrile-imine. 3,6-diphenyl-1,2,4,5-tetrazine (IV); 3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine (III); 3,5-diphenyl-1,2,4-triazole; 4-amino-3,5-diphenyl-1,2,4-triazole; benzonitrile; ammonia and nitrogen were isolated as final products of this reaction.

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Preparation of Si(Al)ON Precursor Using Organoaluminum Imine and Poly (Phenyl Carbosilane), and the Compositional Change of the Film with Different Heat Treatment Condition

  • Lee, Yoonjoo;Shin, Dong-Geun;Kwon, Woo Teck;Kim, Soo Ryong;Kim, Younghee
    • Journal of the Korean Ceramic Society
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    • v.52 no.4
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    • pp.243-247
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    • 2015
  • Si(Al)ON precursor was synthesized by formation of new Si-N bond using organoaluminum imine and liquid type poly(phenyl carbosilane). It was decomposed between $200-600^{\circ}C$, and the ceramic yield was 51% after pyrolysis. 150 - 200 nm in thickness of coating film was obtained by spin coating method. The precursor was easily oxidized during process because it was unstable in air. However the oxygen content was limited to 0.5 - 0.7 to silicon in heat treatment step. Even though the content of nitrogen was decreased by pyrolysis, Al-N and Si-N bonds were formed in ammonia atmosphere, and Si(Al)ON film was formed with 0.2 in content to silicon.

Synthesis and Tautomerism of Novel Quinoxalines (Part II) (새로운 Quinoxaline류의 합성과 토토머화 현상 (제2보))

  • Ho Sik Kim;Kyung Ok Choi;Woo Sung Lim
    • Journal of the Korean Chemical Society
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    • v.47 no.4
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    • pp.345-353
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    • 2003
  • The reaction of 6-chloro-3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(5) or 3-methoxycarbonylmethylene-6-nitro-2-oxo-1,2,3,4-tetrahydroquinoxaline(6) with hydrazine hydrate gave 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxalines(7, 8). The reaction of compound 7 or 8 with substituted benzaldehydes or heteroaromatic aldehydes afforded quinoxalines(9-14). Compounds showed the tautomerism between the enamine and methylene imine forms, and between the enamine, methylene imine and enaminol forms in dimethyl sulfoxide solution. The tautomer ratios were determined by the 1H NMR.

Synthesis of Novel 1,2,4-Triazole Derivative (새로운 1,2,4-Triazole 유도체의 합성에 관한 연구)

  • Kim, Ho Sik;Park Tae Joo;Doh Yi Hyang;Lee Man Kil;Kurasawa Yoshihisa
    • Journal of the Korean Chemical Society
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    • v.36 no.5
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    • pp.738-743
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    • 1992
  • ${\alpha}-Arylhydrazonoacylazide(7) was synthesized starting from {\circo}-phenylenediamine(3) in four steps. The tautomeric behavior of {\alpha}-arylhydrazonoacylazide(7) between the hydrazone imine and diazenyl enamine forms in the dimethyl sulfoxide solution was investigated on the basis of the tautomer ratio determined by the ^1H-NMR spectral data. The 1-aryl-3-quinoxalinyl-1,2,4-triazol(8) was synthesized from {\alpha}-arylhydrazonoacylazide(7) by refluxing in benzene.$

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Synthesis and Tautomerism of Pyrazoles and N-Phenylethanamides with Quinoxaline Ring (Quinoxaline 고리를 가진 Pyrazole류 및 N-Phenylethanamide류의 합성과 토토머화 현상)

  • Kim, Ho Sik;Choi, Kyung Ok;Lee, Hyong Choul;Kwag, Sam Tag;Yoshihisa Kurasawa
    • Journal of the Korean Chemical Society
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    • v.45 no.5
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    • pp.454-460
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    • 2001
  • The reaction of 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(7) with hydrazine hydrate gave 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(8). The reaction of compound 8 with alkyl (ethoxymethylene)cyanoacetates gave the [(quinoxalin-2-ylidene)ethanoyl]-1H-pyra-zoles(9). The reaction of compound 9b with N-alkylanilines provided the N-alkyl-(quinoxalin-2-ylidene)-N-phenylethanamides(10). Compounds 9 and 10 showed the tautomerism between the enamine and methylene imine forms in solution. The tautomer ratios were determined by the $^1H$ NMR.

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Studies on The Elution Behavior of Ni(II)-${\alpha}$-isonitroso-${\beta}$-diketone Imine Chelates in Reversed-Phase Liquid Chromatography

  • Lee, Won;Kim, In-Whan;Kim, Mi-Kyoung;Kim, Yong-Jun;Jung, Hae-Rim;No, Kyoung-Tai;Kim, Su-Yeon
    • Analytical Science and Technology
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    • v.8 no.4
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    • pp.519-527
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    • 1995
  • The retention mechanism of Ni(II)-${\alpha}$-isonitroso-${\beta}$-diketone imine chelates in reversed-phase HPLC has been studied by examining the effect of temperature, mobile phase composition in acetonitrile-water mixture, and molecular structure on retention. The empirical retention equation was investigated to evaluate the properties of S (hydrophilic index). The value of the S index of the Ni(II) chelates decrease with the increasing column temperature and a linear relationship between S and log $k{_w}^{\prime}$ has been found. The results showed that the S index is influenced by the interaction between Ni(II) chelates and mobile phase. Molecular properties, van der Waals molar volume, polarizability and dipole moment, of the Ni(II) chelates were calculated by Cerius 2 program and the calculations were performed at Universal Force Field (UFF) model. The S value and log $k{_w}^{\prime}$ increase with decreasing the dipole moment of Ni(II) chelates.

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Allyloxy-and Benzyloxy-Substituted Pyridine-bis-imine Iron(II) and Cobalt(II) Complexes for Ethylene Polymerization

  • Kim Il;Han Byeong Heui;Kim Jae Sung;Ha Chang-Sik
    • Macromolecular Research
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    • v.13 no.1
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    • pp.2-7
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    • 2005
  • A series of ethylene polymerization catalysts based on tridentate bis-imine ligands coordinated to iron and cobalt was reported. The ligands were prepared through the condensation of sterically bulky anilines with allyloxy-and benzyloxy-substituted 2,6-acetylpyridines. The pre-catalyst complexes were penta-coordinate species of the general formula $\{[(ArN=C(Me))_2(4-RO-C_5H_3N)]MCl_2\}$ (Ar=ortho dialkyl-substituted aryl ring; R=allyl, benzyl; M=Fe, Co). In the presence of ethylene and methyl alumoxane cocatalysts, these complexes were active for the polymerization of ethylene, with activities lower than those of metal complexes of the general formula $\{[(2-ArN=C(Me)_2C_5H_3N]MCl_2\}$ (Ar=ortho dialkyl-substituted aryl ring; M=Co, Fe), containing no substituents in 2,6-acetylpyridine ring. The effects of the catalyst structure and temperature on the polymerization activity, thermal properties, and molecular weight were discussed.