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Stereoselective and efficient chemical transformation of aldehydes and two molecules of pyrazolin-5-one into bis(spiropyrazolone)cyclopropanes under a column chromatography-free protocol at room temperature Full article

Journal Monatshefte Fur Chemie
ISSN: 1434-4475 , E-ISSN: 0026-9247
Output data Year: 2023, Volume: 154, Number: 6, Pages: 625-633 Pages count : 9 DOI: 10.1007/s00706-023-03072-5
Authors Elinson Michail N. 1 , Ryzhkova Yuliya E. 1 , Ryzhkov Fedor V. 1 , Kalashnikova Varvara M. 1 , Maslov Oleg I. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: The new type of chemical one-pot Knoevenagel-Michael reaction with following stereoselective NBS induced cyclization was found: the direct chemical one-pot transformation of aldehydes and two molecules of pyrazolin-5-one into substituted bispyrazolone cyclopropanes in 85–95% yields. This stereoselective one-pot process is very efficient and convenient way to substituted (R*,R*)-bis(spiro-2,4-dihydro-3H-pyrazol-3-one)cyclopropanes – useful compounds for different biomedical applications, using reasonable and non-expansive starting materials. Mild and facile conditions of this chemical cascade one-pot process and simple reasonable non-chromatographic isolation procedure allow excellent substance yields along with superior stereoselectivity.
Cite: Elinson M.N. , Ryzhkova Y.E. , Ryzhkov F.V. , Kalashnikova V.M. , Maslov O.I.
Stereoselective and efficient chemical transformation of aldehydes and two molecules of pyrazolin-5-one into bis(spiropyrazolone)cyclopropanes under a column chromatography-free protocol at room temperature
Monatshefte Fur Chemie. 2023. V.154. N6. P.625-633. DOI: 10.1007/s00706-023-03072-5 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:000982061200001
≡ Scopus: 2-s2.0-85158149252
≡ OpenAlex: W4368372506
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