Aminomethylation of morpholinium and N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates
Konstantin А Frolov
1
,
Sergey G Krivokolysko
1
,
Tatyana M Pekhtereva
3
,
Sergey Yu Suykov
3
,
Elena S Papayanina
4
,
Artem О Dmitrienko
5
,
Ivan S. Bushmarinov
5
Publication type: Journal Article
Publication date: 2016-02-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
The structure of reaction products obtained from 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates, primary amines, and formaldehyde substantially depends on the nature of counter-ion (morpholinium or N-methylmorpholinium), as well as on the primary amine structure and the ratio of reactants. Aminomethylation of these thiolates with highly nucleophilic amines RCH2NH2 and excess formalin (2 equiv and more) produced 7-RCH2-9,9-dimethyl-2-oxo-4-thioxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarbonitrile salts, which gave the respective bispidines upon acidification. Performing this reaction with aromatic amines in the case of N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate led to analogous bispidines, while the morpholinium salt gave 3-aryl-8,8-dimethyl-7-[(morpholin-4-yl)methyl]-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-7,9-dicarbonitriles. The treatment of thiolates with 1 equiv of НСНО and 1 equiv of RCH2NH2 led to 7-RCH2-4-amino-9,9-dimethyl-2-oxo-6-thioxo-3,7-diazabicyclo[3.3.1]non-3-ene-1-carbonitriles. The molecular and crystal structures of key compounds were studied in detail by X-ray structural analysis.
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Total citations:
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Citations from 2024:
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Dotsenko V. V. et al. Aminomethylation of morpholinium and N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates // Chemistry of Heterocyclic Compounds. 2016. Vol. 52. No. 2. pp. 116-127.
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Dotsenko V. V., Frolov K. А., Krivokolysko S. G., Chigorina E. A., Pekhtereva T. M., Suykov S. Yu., Papayanina E. S., Dmitrienko A. О., Bushmarinov I. S. Aminomethylation of morpholinium and N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates // Chemistry of Heterocyclic Compounds. 2016. Vol. 52. No. 2. pp. 116-127.
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TY - JOUR
DO - 10.1007/s10593-016-1843-5
UR - https://doi.org/10.1007/s10593-016-1843-5
TI - Aminomethylation of morpholinium and N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates
T2 - Chemistry of Heterocyclic Compounds
AU - Dotsenko, Victor V
AU - Frolov, Konstantin А
AU - Krivokolysko, Sergey G
AU - Chigorina, Elena A
AU - Pekhtereva, Tatyana M
AU - Suykov, Sergey Yu
AU - Papayanina, Elena S
AU - Dmitrienko, Artem О
AU - Bushmarinov, Ivan S.
PY - 2016
DA - 2016/02/01
PB - Springer Nature
SP - 116-127
IS - 2
VL - 52
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2016_Dotsenko,
author = {Victor V Dotsenko and Konstantin А Frolov and Sergey G Krivokolysko and Elena A Chigorina and Tatyana M Pekhtereva and Sergey Yu Suykov and Elena S Papayanina and Artem О Dmitrienko and Ivan S. Bushmarinov},
title = {Aminomethylation of morpholinium and N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates},
journal = {Chemistry of Heterocyclic Compounds},
year = {2016},
volume = {52},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007/s10593-016-1843-5},
number = {2},
pages = {116--127},
doi = {10.1007/s10593-016-1843-5}
}
Cite this
MLA
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Dotsenko, Victor V., et al. “Aminomethylation of morpholinium and N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates.” Chemistry of Heterocyclic Compounds, vol. 52, no. 2, Feb. 2016, pp. 116-127. https://doi.org/10.1007/s10593-016-1843-5.
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