This article is cited in 4 scientific papers (total in 4 papers)
Communications
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
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.
Citation:
M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, K. A. Karpenko, I. E. Ushakov, “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 Commun., 31:5 (2021), 698–700
Linking options:
https://www.mathnet.ru/eng/mendc1027
https://www.mathnet.ru/eng/mendc/v31/i5/p698
This publication is cited in the following 4 articles:
M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, K. A. Karpenko, T. M. Iliyasov, V. M. Kalashnikova, M. P. Egorov, “Multicomponent synthesis of new barbituric acid derivatives”, Russ Chem Bull, 73:5 (2024), 1286
M. N. Elinson, Yu. E. Ryzhkova, V. M. Kalashnikova, A. O. Chizhov, A. N. Fakhrutdinov, M. P. Egorov, “First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings”, Mendeleev Commun., 34:6 (2024), 865–867
Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Artem N. Fakhrutdinov, Michail N. Elinson, “Green multicomponent approach to novel 5‐[(2H‐Pyran‐3‐yl)(aryl)methyl]‐1,3‐dimethylpyrimidines”, Journal of Heterocyclic Chem, 60:4 (2023), 576
M. N. Elinson, A. N. Vereshchagin, Y. E. Ryzhkova, K. A. Karpenko, I. E. Ushakov, O. I. Maslov, M. P. Egorov, “Four-component transformation of benzaldehydes, dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one, and morpholine into the unsymmetrical ionic scaffold with three different heterocyclic rings”, Russ Chem Bull, 71:3 (2022), 464