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Uncommon Ozonolysis of 2,3-Seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile

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Abstract

The oxidation of 2,3-seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile with ozone in methylene chloride at –40°C afforded a mixture of 4,20-dioxo-2,3-seco-23,24,28,29-tetranorlupane-2,17-dicar­bonitrile (71%), 4,20-dioxo-3,30-dihydroxy-2,3-seco-23,24,28,29-tetranorlupane-2,17-dicarbonitrile (15%), 2,17-dicyano-2,4-seco-3,23,24,28,29,30-hexanorlupane-4,20-dioic acid (7%), and 30-hydroxy-2,4-seco-3,23,24,28,29-pentanorlupan-4-oic acid (4%). The product structure was determined by NMR spectroscopy using two-dimensional shift correlation techniques.

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ACKNOWLEDGMENTS

The NMR and mass spectra were recorded using the equipment of the Chemistry joint center (Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences) and Agidel regional joint center (Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment (project nos. AAAA-A20-120012090023-8, AAAA- A20-120012090029-0).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    E. F. Khusnutdinova, I. P. Baikova, A. N. Lobov & O. B. Kazakova

Authors
  1. E. F. Khusnutdinova
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  2. I. P. Baikova
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  3. A. N. Lobov
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  4. O. B. Kazakova
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Corresponding author

Correspondence to O. B. Kazakova.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 9, pp. 1260–1266 https://doi.org/10.31857/S0514749221090044.

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Khusnutdinova, E.F., Baikova, I.P., Lobov, A.N. et al. Uncommon Ozonolysis of 2,3-Seco-24,28-dinorlupa-4(23),20(29)-diene-2,17-dicarbonitrile. Russ J Org Chem 57, 1412–1416 (2021). https://doi.org/10.1134/S1070428021090049

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