• 제목/요약/키워드: malononitrile

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Structural Analysis for the Single Crystal of 2-(4-(9H-carbazol-9-yl)benzylidene) based Dye Compound

  • Hwang, Jiyong;Son, Young-A
    • Textile Coloration and Finishing
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    • v.26 no.2
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    • pp.143-149
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    • 2014
  • The designed dye material, namely 2-(4-(9H-carbazol-9-yl)benzylidene) compound, was synthesized. After the reaction, the solid was filtered and purified by recrystalization with acetone/water. To confirm and analyze its synthesis and structural formation, the single crystal was prepared and its measurement was carried out. A yellow needle crystal of $C_{22}H_{13}N_3$ were made on a Rigaku R-AXIS RAPID diffractometer using graphite monochromated CuK${\alpha}$ radiation. All details were suggested and introduced to support and communicate this study.

Synthesis of Certain Mercapto and Aminopyrimidine Derivatives as Potential Antimicrobial Agents

  • El-Kerdawy, M.M.;Eisa, H.M.;El-Emam, A.A.;Massoud, M.A.;Nasr, M.N.
    • Archives of Pharmacal Research
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    • v.13 no.2
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    • pp.142-146
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    • 1990
  • Reaction of ethyl 4-chloro-2-phenylpyrimidine-4-carboxylate (4) with 5-chloro-2-methylthiophenol or 3-aryl-4-phenyl-1, 2, 4-triazole-5 thiol yielded the corresponding thioethers (5) and (8a, b), respectively. Careful alkaline hydrolysis of (5) yielded the corresponding carboxylic acid (6). Reaction of (4) with p-aminoacetophenone yielded compound (10) which was reacted with certain aromatic aldehyde to afford the$\alpha,\beta$-unsaturated ketones (11a-d). Condensation of (11a-d) with malononitrile or phenylhydrazine yielded the 2-amino-3-cyanopyridines (12a-f) or the 2-pyrazolines (13a, b) respectively. Seven representative compounds were tested for their in vitro antimicrobial activity against some pathogenic micro-organisms, some of them were proved to be active.

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Cure Reaction and Thermal Stability of DGEBA/MDA/MN/HQ System (DGEBA/MDA/MN/HQ계의 경화반응과 열적 안정성)

  • Sim, Mi-Ja;Kim, Sang-Uk
    • Korean Journal of Materials Research
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    • v.5 no.5
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    • pp.606-610
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    • 1995
  • Diglycidyll ether of bisphenol A(DGEBA)/4, 4'-methylene dianiline(MDA)계에 반응성 첨가제 malononitrile(MN)을 첨가하면 내충격성은 크게 향상되나 반응속도는 감소하게 된다. 에폭시 수지의 경화반응은 에폭시기가 개환되어 생성되는 히드록시기가 촉매로 작용하는 자촉매 반응이며, 외부에서도입된 히드록시기도 같은 효과를 나타낸다. 따라서 본 연구에서는 DGEBA/MDA/MN 계의경화 반응속도를 증가시키기 위해 히드록시기를 가진 촉매로서 hydroquinone(HQ)을 도입하였고 이들 계의경화특성 및 열적성질을 고찰하였다. HQ가 첨가됨으로 인해 활성화 에너지는 감속하고 속도상수는 증가하였으며, 발열곡선에서 반응 시작온도가 낮아졌다. 이 결과로부터 HQ가 반응 가속제로 작용하고 있음을 알 수 있다.

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Ultrasound Mediated, Sodium Bisulfite Catalyzed, Solvent Free Synthesis of 6-Amino-3-methyl-4-substitued-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

  • Darandale, Sunil N.;Sangshetti, Jaiprakash N.;Shinde, Devanand B.
    • Journal of the Korean Chemical Society
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    • v.56 no.3
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    • pp.328-333
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    • 2012
  • A simple, convenient and practical green synthetic protocol for sodium bisulfite catalyzed multicomponent reaction of ethyl acetoacetate, hydrazine hydrate, malononitrile, and various aldehydes for the synthesis of 6-amino-4-phenyl-3-methyl-2,4-ihydropyrano[2,3-c]pyrazole-5-carbonitriles using ultrasound irradiations in solvent free condition. This method provides the advantage of operational simplicity, shorter reaction time and excellent yields making the protocol environment friendly and economically lucrative.

A Study on the Preparation of 2,4-Diamino-7-Phenyl-6-Mehylthiopteridine (2,4-Diamino-7-phenyl-6-methythiopteridine 합성에 관한 연구)

  • Park, Nae-Joung;Kim, Myung-Woong;Lee, Jong-Chan
    • Journal of the Korean Applied Science and Technology
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    • v.4 no.1
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    • pp.61-66
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    • 1987
  • 2,4,6-Triamino-5-nitrosopyrimidine was prepared using malononitrile and guanidine carbonate, and acetylated refluxing in acetic acid with acetic anhydride in order to activate the nitroso group for nucleophilic attack. Nucleophilic attack of phenylpyrimidium bromide on the nitroso group of 2,4,6-triacetamido-5-nitrosopyrimidine gave the intermediate, which lost pyrdidine to give the nitrone derivative. Addition of the methanethiol anion to nitrone gave 2,4-diacetamido-7-phenyl-6-methylthiopteridine which was hydrolyzed to give 2,4-diamino-7-phenyl-6-methylthiopteridine. Spectral data (IR, M.S, NMR) were provided to identify the reaction products during synthesis.

Synthesis of Highly Crosslinked Temperature-resistant Poly(vinyl ethers) by Free Radical Polymerization

  • 이주연;김지향
    • Bulletin of the Korean Chemical Society
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    • v.19 no.8
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    • pp.851-856
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    • 1998
  • 2,4-Di-(2-vinyloxyethoxy)benzylidenemalononitrile (2a), methyl 2,4-di-(2-vinyloxyethoxy)benzylidenecyanoacetate (2b), 3,4-di-(2-vinyloxyethoxy)benzylidenemalononitrile (4a), and methyl 3,4-di-(2-vinyloxyethoxy)benzylidenecyanoacetate (4b), 2,5-di-(2-vinyloxyethoxy)benzylidenemalononitrile (6a), and methyl 2,5-di-(2-vinyloxyethoxy)benzylidenecyanoacetate (6b) were prepared by the condensation of 2,4-di-(2-vinyloxyethoxy)benzaldehyde (1), 3,4-di-(2-vinyloxyethoxy)benzaldehyde (3), and 2,5-di-(2-vinyloxyethoxy)benzaldehyde (5) with malononitrile or methyl cyanoacetate, respectively. Trifunctional divinyl ether monomers 2, 4 and 6 were polymerized readily by free radical initiators to give optically transparent swelling poly(vinyl ethers) 7-9. Polymers 7-9 were not soluble in common organic solvents such as acetone and DMSO due to crosslinking. Polymer 7-9 showed a thermal stability up to 300 ℃ in TGA thennograms.

Hydroxy-Substituted Polyenaminonitrile as a Soluble Precursor for Rigid-Rod Polybenzoxazole

  • Kim, Ji Heung;Lee, Jae Gwan
    • Bulletin of the Korean Chemical Society
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    • v.22 no.9
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    • pp.999-1004
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    • 2001
  • (1-Chloro-2,2-dicyanovinyl)benzene or 1,4-bis(1-chloro-2,2-dicyanovinyl)benzene was reacted with 2-amino-phenol to give the model compound, hydroxy enaminonitrile, which was found to undergo thermal cyclization reaction to form the corresponding benzoxazole. This intramolecular cyclization reaction is expected to occur through nucleophilic attack to electropositive enamine carbon by ortho-hydroxy group on the phenyl ring, which is accompanied by the release of neutral malononitrile through rearrangement. From each bifunctional monomer, o-hydroxy substituted polyenaminonitrile was prepared and characterized as a new precursor polymer for well-known aromatic polybenzoxazole. Also the unusual macrocyclic dimer formation from the 1,4-bis(1-chloro-2,2-dicyanovinyl)benzene and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane polymerization reaction system was discussed. The thermal cyclization reactions and the properties of polymers were investigated using FT-IR and thermal analysis (DSC & TGA).

Synthesis and Cationic Polymerization of Vinyl Ethers Containing Oxynitrobenzylidenemalononitrile and Oxynitrobenzylidenecyanoacetate as the NLO-phores in the Side Chain

  • 이주연;김무용;안미라
    • Bulletin of the Korean Chemical Society
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    • v.20 no.5
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    • pp.567-572
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    • 1999
  • 5-Nitro-2-(2'-vinyloxyethoxy)benzylidenemalononitrile (2a), methyl 5-nitro-2-(2'-vinyloxyethoxy)benzylidenecyanoacetate (2b), 3-nitro-4-(2'-vinyloxyethoxy)benzylidenemalononitrile (4a), methyl 3-nitro-4-(2'-vinyloxyethoxy)benzylidenecyanoacetate (4b), 2-nitro-5-(2'-vinyloxyethoxy)benzylidenemalononitrile (6a), and methyl 2-nitro-5-(2'-vinyloxyetboxy)benzylidenecyanoacetate (6b) were prepared by the condensation of 5-nitro-2-(2'-vinyloxyethoxy)benzaldehyde (1), 3-nitro-4-(2'-vinyloxyethoxy)benzaldehyde (3), and 2-nitro-5-(2'-vinyloxyethoxy)benzaldehyde (5) with malononitrile or methyl cyanoacetate, respectively. Vinyl ether monomers 2a-b, 4a-b, and 6a-b were polymerized with boron trifluoride etherate as a cationic initiator to yield poly(vinyl ethers) 7-9 having oxynitrobenzylidenemalononitrile and oxynitrobenzylidenecyanoacetate, which is effective chromophore for second-order nonlinear optical applications. Polymers 7-9 were soluble in common organic solvents such as acetone and DMSO. Tg values of the resulting polymers were in the range of 67-83 ℃. Electrooptic coefficient (r33) of the poled polymer films were in the range of 15-27 pm/V at 633 nm. Polymers 7-9 showed a thermal stability up to 300 ℃ in TGA thermograms, which is acceptable for NLO device applications.

Steric Hindrance in the Free Radical Polymerization of Aryloxyethyl Vinyl Ethers Containing Electron-Deficient Olefin Groups$^{\dag}$

  • Lee, Ju Yeon;Jin, Mi Gyeong
    • Bulletin of the Korean Chemical Society
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    • v.21 no.6
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    • pp.613-617
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    • 2000
  • p-(2-Vinyloxyethoxy)benzylidenemalononitrile (4a), methyl p-(2-vinyloxyethoxy)benzylidenecyanoacetate (4b), 3,5-dimethoxy-4-(2'-vinyloxyethoxy)benzylidenemalononitrile (5a), methyl 3,5-dimethoxy-4-(2'-vinyloxy-ethoxy) benzylidenecyanoacetate (5 b), o-(2 -vinyloxyethoxy)benzylidenemalononitrile (6a), methyl o-(2-viny-Ioxyethoxy) benzylidenecyanoacetate (6b), 1,3-di-(2',2'-dicyanovinyl)-5-methyl-2-(2'-vinyloxyetioxy)benzene (7a), l,3-di-(2'-carbomethoxy-2'-cyanovinyl)-5-methyl-2-(2'-vinyloxyethoxy)benzene (7b), 2,3,4-tri-(2'-viny-Ioxyethoxy) benzylidenemalononitrile (8a), methyl 2,3,4-tri-(2'-vinyloxyethoxy)benzylidenecyanoacetate (8b), 2,4,6-tri-(2'-vinyloxyethoxy)benzylidenemalononitrile (9a), and methyl 2,4,6-tri-(2'-vinyloxyethoxy)benzyl-idenecyanoacetate(9b) were prepared by the condensation of the corresponding benzaldehyde 1-3 with malononitrile or methyl cyanoacetate, respectively. Vinyl ether monomers 4, 6, and 8 polymerized readily with radical initiators to yield crosslinked polymers 10, 12, and 14. However, compounds 5, 7, and 9 were inert to radical initiators due to the steric hindrance. The resulting polymers 10, 12, and 14 were not soluble in common solvents showing a thermal stability up to $300^{\circ}C$.

Synthesis and Cationic Polymerization of Vinyl Ethers Containing the NLO-chromophores Oxybenzylidenemalononitrile and Oxybenzylidenecyanoacetatate in the Side Chain

  • 이주연;김무용;김지향
    • Bulletin of the Korean Chemical Society
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    • v.19 no.2
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    • pp.155-159
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    • 1998
  • o-(2-Vinyloxyethoxy)benzylidenemalononitrile (4a), methyl o-(2-vinyloxyethoxy)benzylidenecyanoacetate (4b), m-(2-vinyloxyethoxy)benzylidenemalononitrile (5a), methyl m-(2-vinyloxyethoxy)benzylidenecyanoacetate (5b), p-(2-vinyloxyethoxy)benzylidenemalononitrile (6a), and methyl p-(2-vinyloxyethoxy)benzylidenecyanoacetate (6b) were prepared by the condensation of o-(2-vinyloxyethoxy)benzaldehyde (1), m-(2-vinyloxyethoxy)benzaldehyde (2), and p-(2-vinyloxyethoxy)benzaldehyde (3) with malononitrile or methyl cyanoacetate, respectively. Bifunctional vinyl ether monomers 4a-b and 6a-b polymerized readily with cationic initiators to give polymers with the NLO-chromophores o- and p-oxybenzylidenemalononitrile or o- and p-oxybenzylidenecyanoacetate in side chain at -60 ℃, while meta-isomers 5a and 5b gave lower yields of polymers under the same conditions. The resulting polymers 7-9 were soluble in common organic solvents and the inherent viscosities of polymers were in the range of 0.20-0.30 dL/g in acetone. Solution-cast films were clear and brittle, showing Tg values in the range of 40-70 ℃.