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Mendeleev Communications, 2021, Volume 31, Issue 5, Pages 698–700
DOI: https://doi.org/10.1016/j.mencom.2021.09.035
(Mi mendc1027)
 

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

M. N. Elinsona, A. N. Vereshchagina, Yu. E. Ryzhkovaa, K. A. Karpenkoa, I. E. Ushakovb

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
Full-text PDF (392 kB) Citations (4)
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.
Keywords: multicomponent reaction, benzaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one, morpholine, tandem Knoevenagel–Michael reaction.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (2.3 Mb)


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
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  • https://www.mathnet.ru/eng/mendc1027
  • https://www.mathnet.ru/eng/mendc/v31/i5/p698
  • This publication is cited in the following 4 articles:
    1. 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  crossref
    2. 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  mathnet  crossref
    3. 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  crossref
    4. 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  crossref
    Citing articles in Google Scholar: Russian citations, English citations
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