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On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones

, 
Anatoly Nikolaevich Vereshchagin 1
Anatoly Nikolaevich Vereshchagin
, 
Yuliya Evgenievna Anisina 1
Yuliya Evgenievna Anisina
, 
Natalia A Leonova 1, 2
Natalia A Leonova
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
10.1016/j.mencom.2020.01.005
Published 2019-12-30
Communication , Volume 30, Issue 1, 15-17
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Elinson M. N. et al. On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 15-17.
GOST all authors (up to 50) Copy
Elinson M. N., Vereshchagin A. N., Anisina Y. E., Leonova N. A., Egorov M. P. On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 15-17.
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TY - JOUR
DO - 10.1016/j.mencom.2020.01.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.005
TI - On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones
T2 - Mendeleev Communications
AU - Elinson, Michail Nikolaevich
AU - Vereshchagin, Anatoly Nikolaevich
AU - Anisina, Yuliya Evgenievna
AU - Leonova, Natalia A
AU - Egorov, Mikhail Petrovich
PY - 2019
DA - 2019/12/30
PB - Mendeleev Communications
SP - 15-17
IS - 1
VL - 30
ER -
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@article{2019_Elinson,
author = {Michail Nikolaevich Elinson and Anatoly Nikolaevich Vereshchagin and Yuliya Evgenievna Anisina and Natalia A Leonova and Mikhail Petrovich Egorov},
title = {On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones},
journal = {Mendeleev Communications},
year = {2019},
volume = {30},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.005},
number = {1},
pages = {15--17},
doi = {10.1016/j.mencom.2020.01.005}
}
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Elinson, Michail Nikolaevich, et al. “On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones.” Mendeleev Communications, vol. 30, no. 1, Dec. 2019, pp. 15-17. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.005.

Abstract

Heating aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones in water results in fast formation of Knoevenagel–Michael adducts in 82–98% yields. This multicomponent process opens facile, efficient and environmentally benign way to the new functionalized [(2-hydroxy-6-oxocyclohex-1-en-1-yl)(aryl)methyl]pyrimidine-2,4(1H,3H)-diones bearing both barbituric acid and cyclohexane-1,3-dionemoieties separated by arylmethylene spacer, which are promising compounds for biomedical applications including analeptics, anti-AIDS and anticancer remedies.

References

1.
10.1016/j.mencom.2020.01.005_bib0005
Organic Reactions in Water: Principles, Strategies and Applications, 2007
2.
Green chemistry oriented organic synthesis in water
Simon M., Li C.
Chemical Society Reviews, 2012
3.
“On Water”: Unique Reactivity of Organic Compounds in Aqueous Suspension
Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., Sharpless K.B.
Angewandte Chemie - International Edition, 2005
5.
Fast reactions ‘on water’
Klijn J.E., Engberts J.B.
Nature, 2005
6.
Organic Synthesis “On Water”
Chanda A., Fokin V.V.
Chemical Reviews, 2009
7.
10.1016/j.mencom.2020.01.005_bib0035
Multicomponent Reactions, 2005
8.
Elinson M.N., Vereshchagin A.N., Anisina Y.E., Goloveshkin A.S., Ushakov I.E., Egorov M.P.
Mendeleev Communications, 2018
9.
Vereshchagin A.N., Karpenko K.A., Elinson M.N., Dorofeeva E.O., Goloveshkin A.S., Egorov M.P.
Mendeleev Communications, 2018
10.
Elinson M.N., Vereshchagin A.N., Anisina Y.E., Krymov S.K., Fakhrutdinov A.N., Egorov M.P.
Mendeleev Communications, 2019
11.
Organic synthesis reactions on-water at the organic–liquid water interface
Butler R.N., Coyne A.G.
Organic and Biomolecular Chemistry, 2016
12.
Demchuk D.V., Elinson M.N., Nikishin G.I.
Mendeleev Communications, 2011
15.
Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis
Gawande M.B., Bonifácio V.D., Luque R., Branco P.S., Varma R.S.
Chemical Society Reviews, 2013
16.
Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists
Evans B.E., Rittle K.E., Bock M.G., DiPardo R.M., Freidinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S., Lotti V.J., Cerino D.J., Chen T.B., Kling P.J., Kunkel K.A., et. al.
Journal of Medicinal Chemistry, 1988
19.
5-Benzylbarbituric acid derivatives, potent and specific inhibitors of uridine phosphorylase.
Naguib F.N., Levesque D.L., Eng-Chi Wang, Panzica R.P., El Kouni M.H.
Biochemical Pharmacology, 1993
20.
Pyrimidine-2,4,6-Triones: A New Effective and Selective Class of Matrix Metalloproteinase Inhibitors
Grams F., Brandstetter H., DAlò S., Geppert D., Krell H., Leinert H., Livi V., Menta E., Oliva A., Zimmermann G.
Biological Chemistry, 2001
21.
Anti-Invasive, Antitumoral, and Antiangiogenic Efficacy of a Pyrimidine-2,4,6-trione Derivative, an Orally Active and Selective Matrix Metalloproteinases Inhibitor
Maquoi E., Sounni N.E., Devy L., Olivier F., Frankenne F., Krell H., Grams F., Foidart J., Noël A.
Clinical Cancer Research, 2004
23.
Elinson M.N., Ilovaisky A.I., Merkulova V.M., Zaimovskaya T.A., Nikishin G.I.
Mendeleev Communications, 2011
28.
Molecular structure and spectroscopic investigations combined with hypoglycemic/anticancer and docking studies of a new barbituric acid derivative
Barakat A., Soliman S.M., Elshaier Y.A., Ali M., Al-Majid A.M., Ghabbour H.A.
Journal of Molecular Structure, 2017
30.
Tandem Knoevenagel–Michael-cyclocondensation reactions of malononitrile, various aldehydes and dimedone using acetic acid functionalized ionic liquid
Moosavi-Zare A.R., Zolfigol M.A., Khaledian O., Khakyzadeh V., Farahani M.D., Kruger H.G.
New Journal of Chemistry, 2014