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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2021 Volume 31, Issue 5, Pages 698–700 (Mi mendc1027)

This article is cited 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

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.

Language: English

DOI: 10.1016/j.mencom.2021.09.035



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