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

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 Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 1573-8353 , E-ISSN: 0009-3122

Output data

Year: 2024, Volume: 60, Number: 5-6, Pages: 239-244 Pages count : 6 DOI: 10.1007/s10593-024-03327-x

Authors

Elinson Michail N. ¹ , Vereshchagin Anatoly N. ¹ , Ryzhkova Yuliya E. ¹ , Karpenko Kirill A. ¹ , Kalashnikova Varvara M. ^1,2

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia
2	D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, 125047, Russia

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 4H-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 4H-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.

Elinson M.N. , Vereshchagin A.N. , Ryzhkova Y.E. , Karpenko K.A. , Kalashnikova V.M.
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
Chemistry of Heterocyclic Compounds. 2024. V.60. N5-6. P.239-244. DOI: 10.1007/s10593-024-03327-x WOS Scopus OpenAlex

Web of science:	WOS:001298364100002
Scopus:	2-s2.0-85201643638
OpenAlex:	W4401754341

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