New 1,3-disubstituted 2,2-dimethylcyclopropanes of the isoxazole and pyrazole series were synthesized starting from (+)-3-carene. Olefination of the reductive ozonolysis product of (+)-4-acetyl-2-carene produced 1R-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane, further reaction of which with hydroxylamine or hydrazines led to heterocyclic compounds. It was shown that 3,5-dimethylpyrazoles could be synthesized on the surface of Al2O3 using ultrasonic irradiation. Studies of the antimicrobial activity of heterocyclic derivatives of dibromovinyl-2,2-dimethylcyclopropane found significant fungicidal effects of pyrazoles 8, 10, and 11 with weak antibacterial activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
E. L. D’Ambro, N. Hyttinen, K. H. Moller, S. Iyer, R. V. Otkjar, D. M. Bell, J. Liu, F. D. Lopez-Hilfiker, S. Schobesberger, J. E. Shilling, A. Zelenyuk, H. G. Kjaergaard, J. A. Thornton, and T. Kurten, Environ. Sci. Technol., 56, 2213 (2022).
S. N. Curlat and F. Macaev, Chem. Nat. Compd., 57, 733 (2021).
S. N. Curlat, A. N. Barba, V. V. Boldescu, K. Panekok, and F. Z. Macaev, Chem. Nat. Compd., 55, 269 (2019).
S. Curlat, Chem. J. Mold., 14 (2), 32 (2019).
J. R. Hanson, J. Chem. Res., 39, 677 (2015).
F. Z. Macaev, N. S. Sucman, S. I. Pogrebnoi, L. P. Logina, and A. N. Barba, Chem. Nat. Compd., 50, 103 (2014).
E. B. Benetsky, S. V. Zheglov, T. B. Grishina, F. Macaev, L. P. Bet, V. A. Davankov, and K. N. Gavrilov, Tetrahedron Lett., 48, 8326 (2007).
K. N. Gavrilov, E. B. Benetsky, T. B. Grishina, S. V. Zheglov, E. A. Rastorguev, P. V. Petrovskii, F. Macaev, and V. A. Davankov, Tetrahedron: Asymmetry, 18, 2557 (2007).
F. Macaev and A.V. Malkov, Tetrahedron, 62, 9 (2006).
O. A. Banina, D. V. Sudarikov, P. A. Slepukhin, L. L. Frolova, and A. V. Kuchin, Chem. Nat. Compd., 52, 240 (2016).
H. J. Lee, G. Shan, T. Watanabe, D. W. Stoutamire, S. J. Gee, and B. D. Hammock, J. Agric. Food Chem., 50, 5526 (2002).
G. A. Tolstikov, F. Z. Galin, F. Z. Macaev, and V. K. Ignatyuk, J. Org. Chem. USSR, 25, 2359 (1989).
L. M. Khalilov, A. A. Fatykhov, V. S. Sultanova, F. Z. Makaev, F. Z. Galin, G. A. Tolstikov, and A. A. Panasenko, Chem. Nat. Compd., 25, 231 (1989).
N. Eremia, O. Coseleva, N. Sucman, G. Balan, L. Lupascu, T. Mardari, S. Modvala, and F. Macaev, Gorteria, 63, 207 (2023).
E. Stingaci, M. Zveaghinteva, S. Pogrebnoi, L. Lupascu, V. Valica, L. Uncu, A. Smetanscaia, M. Drumea, A. Petrou, A. Ciric, J. Glamoclija, M. Sokovic, V. Kravtsov, A. Geronikaki, and F. Macaev, Bioorg. Med. Chem. Lett., 30, 127368 (2020).
P. J. Kropp, D. C. Heckert, and T. J. Flautt, Tetrahedron, 24, 1385 (1968).
Acknowledgment
The work was financially supported by Applied Research Projects Nos. 20.80009.5007.17 and 20.80009-8007.14 of the National Agency for Research and Development of the Republic of Moldova.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2024, pp. 114–117.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Cojocari, S.V., Curlat, S.N. & Macaev, F.Z. Synthesis of 1R-cis-Dibromovinyl-2,2-dimethylcyclopropanes of the Isoxazole and Pyrazole Series Based on (+)-3-Carene. Chem Nat Compd 60, 133–137 (2024). https://doi.org/10.1007/s10600-024-04267-w
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-024-04267-w