Home / Publications / Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings

Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings

, 
Anatoly Nikolaevich Vereshchagin 1
Anatoly Nikolaevich Vereshchagin
, 
Yuliya Evgenievna Ryzhkova 1
Yuliya Evgenievna Ryzhkova
, 
Kirill Anatol'evich Karpenko 1
Kirill Anatol'evich Karpenko
, 
Ivan Evgenievich Ushakov 2
Ivan Evgenievich Ushakov
10.1016/j.mencom.2021.09.035
Published 2021-09-08
Communication , Volume 31, Issue 5, 698-700
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Elinson M. N. et al. Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 698-700.
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Elinson M. N., Vereshchagin A. N., Ryzhkova Y. E., Karpenko K. A., Ushakov I. E. Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 698-700.
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TY - JOUR
DO - 10.1016/j.mencom.2021.09.035
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.035
TI - Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings
T2 - Mendeleev Communications
AU - Elinson, Michail Nikolaevich
AU - Vereshchagin, Anatoly Nikolaevich
AU - Ryzhkova, Yuliya Evgenievna
AU - Karpenko, Kirill Anatol'evich
AU - Ushakov, Ivan Evgenievich
PY - 2021
DA - 2021/09/08
PB - Mendeleev Communications
SP - 698-700
IS - 5
VL - 31
ER -
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@article{2021_Elinson,
author = {Michail Nikolaevich Elinson and Anatoly Nikolaevich Vereshchagin and Yuliya Evgenievna Ryzhkova and Kirill Anatol'evich Karpenko and Ivan Evgenievich Ushakov},
title = {Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.035},
number = {5},
pages = {698--700},
doi = {10.1016/j.mencom.2021.09.035}
}
MLA
Cite this
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Elinson, Michail Nikolaevich, et al. “Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 698-700. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.035.

Keywords

N,N'-dimethylbarbituric acid
4-hydroxy-6-methyl-2H-pyran-2-one
benzaldehydes
morpholine
multicomponent reaction
tandem Knoevenagel–Michael reaction

Abstract

A new type of four component tandem Knoevenagel–Michael reaction has been found consisting in the assembly of benzaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine in alcohols, other organic solvents or water at room temperature without catalyst or any other additives, which results in the selective formation of unsymmetrical scaffold with three different heterocyclic rings in 63–98% yields. The crystal structure of morpholinium 5-[(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)(4-nitrophenyl)methyl]-1,3-dimethyl-2,6-dioxo-1,2,3,4-tetrahydropyrimidin-6-olate has been confirmed by X-ray diffraction.

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