- Process for manufacturing bis(2-methoxyethyl)-2,3,6,7-tetracyano-1,4,5,8,9,10-hexazaanthracene
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A process to manufacture substituted tetracyano-hexaazatricyclics with the substitutions occurring at the 9 and 10 hydrogens. The process begins with 2,3-dichloro-5,6-dicyanopyrazine, which is reacted to form the desired tetracyano-hexaazatricyclic. Different process embodiments enable different reaction paths to the desired tetracyano-hexaazatricyclic. Different tetracyano-hexaazatricyclic embodiments include bis(2-methoxyethyl)-2,3,6,7-tetracyano-1,4,5,8,9,10-hexazaanthracene and bis(2-methoxyethoxyethyl)-2,3,6,7-tetracyano-1,4,5,8,9,10-hexazaanthracene.
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Page/Page column 4; 5
(2014/06/11)
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- Structure-property relationships and nonlinear optical effects in donor-substituted dicyanopyrazine-derived push-pull chromophores with enlarged and varied π-linkers
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Thirteen new, stable, push-pull systems featuring dimethylamino and pyrazine-2,3-dicarbonitrile moieties as the donor and acceptor, respectively, and systematically extended and varied π-linkers were prepared and investigated. Evaluation of the measured UV/Vis spectra, electrochemical data (cyclic voltammetry, rotating disc voltammetry, and polarography), X-ray data, and experimentally determined and calculated hyperpolarizability values enabled structure-property studies; these revealed some important structural features that affected the efficiency of intramolecular charge-transfer and nonlinear optical properties in this class ofheterocyclic push-pull chromophores. The charge-transfer transition was most significantly affected by structuralfeatures such as π-linker length, chromophore planarity, and the number of 1,4-phenylene/ethynylene subunits in the π-linker. Linear and nonlinear optical properties of push-pull chromophores featuring a pyrazine-2,3- dicarbonitrile acceptor moiety and dimethylamino donors were modulated by systematic extension and variation of the π-linker. The length and character of the π-linker used significantly influenced the efficiency of the donor-acceptor conjugation and nonlinear responses. Copyright
- Bures, Filip,Cermakova, Hana,Kulhanek, Jiri,Ludwig, Miroslav,Kuznik, Wojciech,Kityk, Iwan V.,Mikysek, Tomas,Ruzicka, Ales
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supporting information; body text
p. 529 - 538
(2012/03/09)
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- Highly efficient synthesis of 5,6-disubstituted-5H-pyrrolo[2,3-b]pyrazine- 2,3-dicarbonitriles through a one-pot palladium-catalyzed coupling reaction/cyclization in water
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A highly efficient one-pot synthesis of 5,6-disubstituted-5H-pyrrolo[2,3-b] pyrazine-2,3-dicarbonitriles is presented. The reaction of 5-(alkyl-arylamino)- 6-chloropyrazine-2,3-dicarbonitriles with phenylacetylene, catalyzed by Pd-Cu, in the presence of SDS as the surfactant in water, leads to the desired products in good-to-high yields.
- Keivanloo, Ali,Bakherad, Mohammad,Nasr-Isfahani, Hossein,Esmaily, Somayeh
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scheme or table
p. 3126 - 3130
(2012/08/08)
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- Preparation of magnesium azaphthalocyanines by cyclotetramerisation of S-substituted 4,5-disulfanylpyrazine-2,3-dicarbonitriles
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Four novel S-substituted 4,5-disulfanylpyrazine-2,3-dicarbonitriles have been obtained in a multistep synthesis from diaminomaleonitrile. Two of these dicarbonitriles, with ethyl or benzyl S-substituents, give pure magnesium azaphthalocyanines in good yields when reacted with magnesium propoxide in propanol and dioxane. Aromatic S-substituents are less stable during the reaction conditions used for cyclisations, and product mixtures are obtained. Acta Chemica Scandinavica 1996.
- Morkved, Eva H.,Holmaas, Lars T.,Kjosen, Helge,Hvistendahl, Georg
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p. 1153 - 1156
(2007/10/03)
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- Synthesis of Pyridoimidazopyrazines from 2,3-Dichloro-5,6-dicyanopyrazine with 2-Aminopyridines
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Novel synthesis of the title compounds by the facile cyclization between 2,3-dichloro-5,6-dicyanopyrazine and various 2-aminopyridines under relatively mild conditions is described.The reactivity depended on the basicity of 2-aminopyridines.
- Suzuki, Toshinobu,Nagae, Yasushi,Mitsuhashi, Keiryo
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p. 1419 - 1421
(2007/10/02)
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