Two-Stage Synthesis of 3-(4-Hydroxyphenyl)-1′,3′,6-trimethyl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone

Two-Stage Synthesis of 3-(4-Hydroxyphenyl)-1′,3′,6-trimethyl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone Full article

Journal

Molbank
ISSN: 1422-8599

Output data

Year: 2026, Volume: 2026, Number: 2, Article number : M2148, Pages count : DOI: 10.3390/m2148

Tags

4-hydroxybenzaldehyde; N,N′-dimethylbarbituric acid; 4-hydroxy-6-methyl- 2H-pyran-2-one; morpholine; N-bromosuccinimide; ionic scaffold; spiro[furo[3,2-c]pyran; tandem Knoevenagel–Michael reaction; cyclization

Authors

Elinson Michail N. ¹ , Kalashnikova Varvara M. ¹ , Ryzhkova Yuliya E. ¹ , Rakitin Oleg A. ¹

Affiliations

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

Spirocyclic compounds are experiencing a research surge due to their unique 3D structure, offering enhanced pharmacological, industrial, and material applications. They are increasingly used in medicinal chemistry to improve drug-like properties, such as solubility and target binding, and are also being utilized for advanced material applications, including electronics and photonics. In this communication, 3-(4-hydroxyphenyl)-1′,3′,6-trimethyl- 2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone was prepared via a two-stage transformation including a tandem Knoevenagel–Michael reaction and NBSinduced cyclization. At the first stage, a previously unknown ionic scaffold, morpholin-4- ium 5-((4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)(4-hydroxyphenyl)methyl)-1,3-dimethyl- 2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate was also isolated. Structures of the newly synthesized compounds were established by 1H and 13C NMR, IR spectroscopy, highresolution mass spectrometry, and elemental analysis.

Elinson M.N. , Kalashnikova V.M. , Ryzhkova Y.E. , Rakitin O.A.
Two-Stage Synthesis of 3-(4-Hydroxyphenyl)-1′,3′,6-trimethyl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone
Molbank. 2026. V.2026. N2. M2148 . DOI: 10.3390/m2148 OpenAlex

Submitted:	Jan 28, 2026
Accepted:	Mar 6, 2026
Published online:	Mar 11, 2026

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