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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

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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.

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1H and 13C NMR spectra for all new compounds are presented in in the supplementary information file.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

    Michail N. Elinson, Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Varvara M. Kalashnikova & Oleg I. Maslov

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  1. Michail N. Elinson
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  2. Yuliya E. Ryzhkova
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  3. Fedor V. Ryzhkov
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  4. Varvara M. Kalashnikova
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  5. Oleg I. Maslov
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Correspondence to Michail N. Elinson.

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Elinson, M.N., Ryzhkova, Y.E., Ryzhkov, F.V. et al. 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. Monatsh Chem 154, 625–633 (2023). https://doi.org/10.1007/s00706-023-03072-5

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