Abstract
The electrolysis of pyrazoline-5-ones and activated olefins in the presence of sodium bromide as mediator in alcohols in an undivided cell results in efficient formation of the substituted spirocyclopropylpyrazolones in 50–85 % yields. This novel electrocatalytic process opens a convenient way to functionalized spirocyclopropylpyrazolones—the promising compounds for the different biomedical applications. Thus, the simple electrocatalytic system can produce in an undivided cell under mild conditions the electrochemically induced cascade reaction of pyrazoline-5-ones with activated olefins.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L.A. Wessjohann, W. Brandt, Chem. Rev. 103, 1625 (2003)
F. Brackmann, A. de Meijere, Chem. Rev. 107, 4538 (2007)
C. Laroche, J.-B. Behr, J. Szymoniak, P. Bertus, C. Schutz, P. Vogel, R. Plantier-Royon, Bioorgan, Med. Chem. 14, 4047 (2006)
V.P. Sandanayaka, A.S. Prashad, Y. Yang, R.T. Williamson, Y.I. Lin, T.S. Mansour, J. Med. Chem. 46, 2569 (2003)
T. Jiang, K.L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T.Y.-H. Wub, Y. He, Bioorg. Med. Chem. Lett. 16, 2105 (2006)
T. Jiang, K.L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T. Tuntland, K. Zhang, D. Karanewsky, Y. He, Bioorg. Med. Chem. Lett. 16, 2109 (2006)
S. Devi, A. Nayak, A.S. Mittra, J. Indian Chem. Soc. 61, 640 (1984)
M. Itokawa, T. Miyata, M. Arai, Eur. Pat. Appl. EP 2 189 537 A1 (2010)
J. Elguero, in ed. by A.R. Katritzky, C.W. Rees, E.F.V. Scrive. Comprehensive Heterocyclic Chemistry II, vol 3 (Pergamon-Elsevier Science, Oxford, 1996)
R. Frankle, R.D. Little, Chem. Soc. Rev. 43, 2492 (2014)
Y.N. Ogibin, M.N. Elinson, G.I. Nikishin, Russ. Chem. Rev. 78, 89 (2009)
M.N. Elinson, E.O. Dorofeeva, A.N. Vereshchagin, G.I. Nikishin, Russ. Chem. Rev. 84, 485 (2015)
G.I. Nikishin, M.N. Elinson, S.K. Feducovich, Russ. Chem. Bull. 35, 1749 (1986)
M.N. Elinson, T.L. Lizunova, M.O. Dekaprilevich, Y.T. Struchkov, G.I. Nikishin, Mendeleev Commun. 3, 192 (1993)
M.N. Elinson, A.N. Vereshchagin, N.O. Stepanov, T.A. Zaimovskaya, V.M. Merkulova, G.I. Nikishin, Tetrahedron Lett. 51, 428 (2010)
M.N. Elinson, S.K. Feducovich, N.O. Stepanov, A.N. Vereshchagin, G.I. Nikishin, Tetrahedron 64, 708 (2008)
M.N. Elinson, S.K. Feducovich, T.L. Lizunova, G.I. Nikishin, Tetrahedron 56, 3063 (2000)
A.N. Vereshchagin, M.N. Elinson, T.A. Zaimovskaya, G.I. Nikishin, Tetrahedron 64, 9766 (2008)
A.N. Vereshchagin, M.N. Elinson, E.O. Dorofeeva, R.F. Nasybullin, I.S. Bushmarinov, A.S. Goloveshkin, M.P. Egorov, Electrochim. Acta 165, 116 (2015)
M.N. Elinson, S.K. Feducovich, Z.A. Starikova, O.S. Olessova, A.N. Vereshchagin, G.I. Nikishin, Tetrahedron Lett. 41, 4937 (2000)
M.N. Elinson, S.K. Feducovich, Z.A. Starikova, A.N. Vereshchagin, G.I. Nikishin, Tetrahedron 60, 11743 (2004)
M.N. Elinson, S.K. Feducovich, Z.A. Starikova, A.N. Vereshchagin, S.V. Gorbunov, G.I. Nikishin, Tetrahedron Lett. 46, 6389 (2005)
M.N. Elinson, S.K. Feducovich, Z.A. Starikova, A.N. Vereshchagin, G.I.P.A. Belyakov, Nikishin, Tetrahedron 62, 3989 (2006)
Acknowledgments
The authors gratefully acknowledge the financial support of the Russian Foundation for Basic Research (Project No. 15-33-20168).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Elinson, M.N., Dorofeeva, E.O., Vereshchagin, A.N. et al. Simple and facile electrocatalytic approach to medicinally relevant spirocyclopropylpyrazolones directly from pyrazoline-5-ones and activated olefins. Res Chem Intermed 42, 2191–2200 (2016). https://doi.org/10.1007/s11164-015-2142-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2142-y