Multicomponent Selective Assembling Aldehydes, <i>N</i> , <i>N′</i> ‐Dialkylbarbituric Acids, and 4‐Hydroxycoumarin Into Medicinally Relevant Spirobarbituric 2,3‐Dihydro‐ <scp> 4 <i>H</i> </scp> ‐Furo[2,3‐ <i>c</i> ]Chromen‐4‐One Scaffold

ABSTRACT The new type of multicomponent tandem Knoevenagel–Michael reaction with further cyclization was found: the transformation of arylaldehydes, N , N ´‐dialkylbarbituric acids and 4‐hydroxycoumarin by the action of morpholine, and then N ‐bromosuccinimide in ethanol without any other additives at ambient temperature led to selective formation of the medicinally relevant unsymmetrical spirobarbituric 2,3‐dihydro‐4 H ‐furo[2,3‐ c ]chromen‐4‐ones with three pharmacology active heterocyclic rings in 85%–98% yields. This new multicomponent reaction is a simple selective and efficient way to spiro[furo[3,2‐ c ]chromene‐2,5′‐pyrimidines], which are promising compounds for the different biomedical applications, among them anticonvulsants, anti‐AIDS agents, and anti‐inflammatory remedies. This synthetic multicomponent procedure does not require heating, long reaction times, or complex equipment. It is easy to carry out, and the procedure for isolating the final compounds is very simple. This new multicomponent method is applicable for large‐scale processes with modern environmental requirements. All these advantages make this method valuable for the synthesis of new potential biologically active compounds.

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Publication Details

Journal
Journal of Heterocyclic Chemistry
Published
2026-02-18
DOI
https://doi.org/10.1002/jhet.70176
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
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article

Multicomponent Selective Assembling Aldehydes, N , N′ ‐Dialkylbarbituric Acids, and 4‐Hydroxycoumarin Into Medicinally Relevant Spirobarbituric 2,3‐Dihydro‐ 4 H ‐Furo[2,3‐ c ]Chromen‐4‐One Scaffold

Yuliya E. Ryzhkova, Michaïl N. Elinson, Varvara M. Kalashnikova, Mikhail P. Egorov et al.
Journal of Heterocyclic Chemistry
Multicomponent Synthesis of Heterocycles
article

Multicomponent Selective Assembling Aldehydes, N , N′ ‐Dialkylbarbituric Acids, and 4‐Hydroxycoumarin Into Medicinally Relevant Spirobarbituric 2,3‐Dihydro‐ 4 H ‐Furo[2,3‐ c ]Chromen‐4‐One Scaffold

Yuliya E. Ryzhkova, Michaïl N. Elinson, Varvara M. Kalashnikova, Mikhail P. Egorov, Artem N. Fakhrutdinov
article en

Abstract

ABSTRACT The new type of multicomponent tandem Knoevenagel–Michael reaction with further cyclization was found: the transformation of arylaldehydes, N , N ´‐dialkylbarbituric acids and 4‐hydroxycoumarin by the action of morpholine, and then N ‐bromosuccinimide in ethanol without any other additives at ambient temperature led to selective formation of the medicinally relevant unsymmetrical spirobarbituric 2,3‐dihydro‐4 H ‐furo[2,3‐ c ]chromen‐4‐ones with three pharmacology active heterocyclic rings in 85%–98% yields. This new multicomponent reaction is a simple selective and efficient way to spiro[furo[3,2‐ c ]chromene‐2,5′‐pyrimidines], which are promising compounds for the different biomedical applications, among them anticonvulsants, anti‐AIDS agents, and anti‐inflammatory remedies. This synthetic multicomponent procedure does not require heating, long reaction times, or complex equipment. It is easy to carry out, and the procedure for isolating the final compounds is very simple. This new multicomponent method is applicable for large‐scale processes with modern environmental requirements. All these advantages make this method valuable for the synthesis of new potential biologically active compounds.

Journal of Heterocyclic Chemistry
N.D. Zelinsky Institute of Organic Chemistry (RU)
Life in Land
Openalex Percentile: Top 49%
Multicomponent Synthesis of Heterocycles
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