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
1
Shevchenko Lugansk National University, Lugansk, Ukraine
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2
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine
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Publication type: Journal Article
Publication date: 2013-07-01
scimago Q4
wos Q4
SJR: 0.179
CiteScore: 1.4
Impact factor: 0.8
ISSN: 10703632, 16083350
General Chemistry
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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Dyachenko I. 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 // Russian Journal of General Chemistry. 2013. Vol. 83. No. 7. pp. 1383-1393.
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Dyachenko I. V., Rusanov E. B., Gutov A. V., Vovk M. V. 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 // Russian Journal of General Chemistry. 2013. Vol. 83. No. 7. pp. 1383-1393.
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TY - JOUR
DO - 10.1134/s1070363213070141
UR - https://doi.org/10.1134/s1070363213070141
TI - 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
T2 - Russian Journal of General Chemistry
AU - Dyachenko, I V
AU - Rusanov, E. B.
AU - Gutov, A V
AU - Vovk, M V
PY - 2013
DA - 2013/07/01
PB - Pleiades Publishing
SP - 1383-1393
IS - 7
VL - 83
SN - 1070-3632
SN - 1608-3350
ER -
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@article{2013_Dyachenko,
author = {I V Dyachenko and E. B. Rusanov and A V Gutov and M V Vovk},
title = {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},
journal = {Russian Journal of General Chemistry},
year = {2013},
volume = {83},
publisher = {Pleiades Publishing},
month = {jul},
url = {https://doi.org/10.1134/s1070363213070141},
number = {7},
pages = {1383--1393},
doi = {10.1134/s1070363213070141}
}
Cite this
MLA
Copy
Dyachenko, I. 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.” Russian Journal of General Chemistry, vol. 83, no. 7, Jul. 2013, pp. 1383-1393. https://doi.org/10.1134/s1070363213070141.