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Synthesis and alkylation of 1-alkyl(aryl)-4-cyano-3-dicyanomethylene-substituted carbo[c]fused pyridines. Molecular and crystal structure of 2-(4-cyano-1-methyl-5,6,7,8-tetrahydroisoquinolin-3-yl)-2-(2-oxo-2-phenylethyl)malononitrile and 10-amino-8-phenyl-5-(2-chlorophenyl)-1,2,3,4-tetrahydro-7H-pyrido[2′,3′:3,4]cyclopenta[1,2-c]isoquinoline-7,7,9-tricarbonitrile

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Abstract

Condensation of 2-acyl-1-(N-morpholinyl)cycloalkene with malononitrile dimer results in 1-alkyl-(aryl)-4-cyano-3-dicyanomethylene-substituted carbo[c]fused pyridines. Reaction of the latter with alkyl halides affords the corresponding 2-alkyl-2-(3-isoquinolinyl)malononitrile, 1-amino-2-(4-bromobenzoyl)-5-(2-chlorophenyl)-6,7,8,9-tetrahydro-3H-cyclopenta[c]isoquinoline-3,3-dicarbonitrile and 10-amino-8-phenyl-5-(2-chlorophenyl)-1,2,3,4-tetrahydro-7H-pyrido[2′,3′:3,4]cyclopenta[1,2-c]isoquinoline-7,7,9-tricarbonitrile. Structure of the latter and of 2-(1-methyl-4-cyano-5,6,7,8-tetrahydroisoquinolin-3-yl)-2-(2-oxo-2-phenylethyl)-malononitrile was investigated by XRD.

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Authors and Affiliations

  1. Shevchenko Lugansk National University, ul. Oboronnaya 2, Lugansk, 91011, Ukraine

    I. V. Dyachenko

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine

    E. B. Rusanov, A. V. Gutov & M. V. Vovk

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  1. I. V. Dyachenko
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  2. E. B. Rusanov
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  3. A. V. Gutov
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  4. M. V. Vovk
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Correspondence to I. V. Dyachenko.

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Original Russian Text © I.V. Dyachenko, E.B. Rusanov, A.V. Gutov, M.V. Vovk, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 7, pp. 1132–1142.

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Dyachenko, I.V., Rusanov, E.B., Gutov, A.V. et al. Synthesis and alkylation of 1-alkyl(aryl)-4-cyano-3-dicyanomethylene-substituted carbo[c]fused pyridines. Molecular and crystal structure of 2-(4-cyano-1-methyl-5,6,7,8-tetrahydroisoquinolin-3-yl)-2-(2-oxo-2-phenylethyl)malononitrile and 10-amino-8-phenyl-5-(2-chlorophenyl)-1,2,3,4-tetrahydro-7H-pyrido[2′,3′:3,4]cyclopenta[1,2-c]isoquinoline-7,7,9-tricarbonitrile. Russ J Gen Chem 83, 1383–1393 (2013). https://doi.org/10.1134/S1070363213070141

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