Cascade assembling of aldehydes and two molecules of dimedone into 4H-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-triones under column chromatography-free protocol at room temperature

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2024-06, Vol.60 (5-6), p.239-244
• Main Authors: Elinson, Michail N., Vereshchagin, Anatoly N., Ryzhkova, Yuliya E., Karpenko, Kirill A., Kalashnikova, Varvara M.
• Format: Article
• Language: English
• Subjects: Aldehydes; Biomedical materials; Chemical compounds; Chemistry; Chemistry and Materials Science; Column chromatography; Cyclohexane; Michael reaction; Organic Chemistry; Pharmacy; Room temperature; Substitutes
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-024-03327-x

A new type of one-pot Knoevenagel–Michael reaction with the following NBS-induced cyclization was found: a direct one-pot transformation of aldehydes and two molecules of dimedone into substituted 4 H -spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-triones in 86–95% yields. This one-pot process is a very efficient and convenient way to access substituted 4 H -spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-triones – useful compounds for different biomedical applications with reasonable and nonexpensive starting materials. Mild and facile conditions of this chemical cascade one-pot process, as well as non-chromatographic isolation procedure lead to excellent substance yields.