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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

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Abstract

A new type of the four-component tandem Knoevenagel—Michael reaction was discovered. The transformation of arylaldehydes, N,N′-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one, and morpholine in alcohols, other organic solvents, and water without a catalyst or any other additives and without heating leads to the selective formation of a new substituted unsymmetric ionic scaffold with three different heterocyclic rings in 81–98% yields. The structure of the obtained compounds was confirmed by the data of X-ray diffraction analysis.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. N. Elinson, A. N. Vereshchagin, Y. E. Ryzhkova, K. A. Karpenko, O. I. Maslov & M. P. Egorov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    I. E. Ushakov

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  1. M. N. Elinson
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  2. A. N. Vereshchagin
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  3. Y. E. Ryzhkova
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Correspondence to M. N. Elinson.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 464–473, March, 2022.

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Elinson, M.N., Vereshchagin, A.N., Ryzhkova, Y.E. et al. 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, 464–473 (2022). https://doi.org/10.1007/s11172-022-3434-1

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  • DOI: https://doi.org/10.1007/s11172-022-3434-1

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