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 Full article

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2021, Volume: 31, Number: 5, Pages: 698-700 Pages count : 3 DOI: 10.1016/j.mencom.2021.09.035

Authors

Elinson Michail N. ¹ , Vereshchagin Anatoly N. ¹ , Ryzhkova Yuliya E. ¹ , Karpenko Kirill A. ¹ , Ushakov Ivan E. ²

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991,Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation

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.

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. V.31. N5. P.698-700. DOI: 10.1016/j.mencom.2021.09.035 WOS Scopus OpenAlex

Web of science:	WOS:000717972600035
Scopus:	2-s2.0-85119483748
OpenAlex:	W3211029645

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OpenAlex	4
Scopus	3
Web of science	4