Direct four-component assembling of arylaldehydes, dimethylbarbituric acid, 4-hydroxycoumarine, and cyclic amines into complex scaffolds with three different heterocyclic rings

Direct four-component assembling of arylaldehydes, dimethylbarbituric acid, 4-hydroxycoumarine, and cyclic amines into complex scaffolds with three different heterocyclic rings Full article

Journal

Monatshefte Fur Chemie
ISSN: 1434-4475 , E-ISSN: 0026-9247

Output data

Year: 2021, Volume: 152, Number: 11, Pages: 1327-1336 Pages count : 10 DOI: 10.1007/s00706-021-02849-w

Authors

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

Affiliations

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

The new type of four-component tandem Knoevenagel–Michael reaction was found: assembling arylaldehydes, N,N′-dimethylbarbituric acid, 4-hydroxycoumarine, and morpholine or piperidine has been successfully carried out in alcohols, other organic solvents and water at ambient temperature without catalyst or any other additives and resulted in the selective formation of the new substituted unsymmetrical scaffold with three different heterocyclic rings in 75–98% yields. The crystal structure of morpholin-4-ium 5-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(phenyl)methyl]-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate and morpholin-4-ium 5-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(4-nitrophenyl)methyl]-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate was confirmed by X-ray diffraction study. Thus, this new four-component tandem Knoevenagel–Michael strategy is a selective, facile, and efficient way to unsymmetrical scaffolds with three different pharmacology active heterocyclic rings. The optimized reaction conditions and a mechanistic rationale for this multicomponent assembling are presented.

Elinson M.N. , Vereshchagin A.N. , Ryzhkova Y.E. , Karpenko K.A. , Ushakov I.E. , Goloveshkin A.S.
Direct four-component assembling of arylaldehydes, dimethylbarbituric acid, 4-hydroxycoumarine, and cyclic amines into complex scaffolds with three different heterocyclic rings
Monatshefte Fur Chemie. 2021. V.152. N11. P.1327-1336. DOI: 10.1007/s00706-021-02849-w WOS Scopus OpenAlex

Web of science:	WOS:000695813100003
Scopus:	2-s2.0-85114866846
OpenAlex:	W3201132425

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