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Synthesis of ethyl 5-aryl-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-carboxylates, exhibiting plant growth-regulating properties

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Abstract

A convenient method for the synthesis of high-boiling-point α-(trifluoromethyl)styrenes was proposed. The regioselective synthesis of a series of ethyl 5-aryl-5-(trifluoromethyl)-4,5- dihydroisoxazole-3-carboxylates was conducted by the reaction of ethyl nitroacetate with α-(trifluoromethyl)styrenes in the presence of 1,4-diazabicyclo[2.2.2]octane as a catalyst. The effect of the resulting compounds on seed germination and root formation was studied.

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References

  1. A. I. Kotyatkina, V. N. Zhabinsky, V. A. Khripach, Russ. Chem. Rew., 2001, 70, 641.

    Article  Google Scholar 

  2. A. K. Kumar, M. M. Jovindaraju, N. Renuca, G. V. Kurnar, J. Chem. Pharm. Res., 2015, 7, 250.

    Google Scholar 

  3. M. M. M. Santos, N. Faria, J. Iley, J. Coles, M. B. Hursthouse, M. Luz Martins, R. Moreira, Biorg. Med. Chem. Lett., 2010, 20, 193.

    Article  Google Scholar 

  4. B. Sailu, M. Srinivas, S. A. Satya, B. Balram, B. Ram, B. Taara, B. Vasudha, Der. Pharm. Chem., 2012, 4, 2036.

    Google Scholar 

  5. J. Skommer, D. Wlodcowic, M. Matto, M. Eray, J. Pelkonen, Leukemia Res., 2006, 30, 322.

    Article  Google Scholar 

  6. S. Kasibhatla, H. Gourdeau, K. Meerovitch, J. Drewe, S. Reddy, L. Qiu, H. Zhang, F. Bergeron, D. Boufard, Q. Yang, J. Herich, S. Lamothe, S. Xiong, B. Tseng, Mol. Cancer Ther., 2004, 3, 1365.

    Google Scholar 

  7. Yu. Ya. Spiridonov, G. E. Larina, V. G. Shestakov, Metodicheskoe rukovodstvo po izucheniyu gerbitsidov, primenyaemykh v rastenievodstve [Methodological Guidelines for the Study of Herbicides Used in Plant Growing], Pechatnyi Gorod, Moscow, 2009, 252 pp. (in Russian).

    Google Scholar 

  8. JP Pat. WO 2004018410 (A1) 20040304, 2004.

  9. JP Pat. WO 2005085216 (A1) 20050915, 2005.

  10. DE Pat. WO 2014135606 (A1) 20140912, 2014.

  11. EP 2964019 A1 20160113, 2016.

  12. US Pat. US 20160015028 A1 20160121, 2016.

  13. J. P. Begue, D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, John Wiley and Sons, Hoboken, 2008, 365 pp.

    Book  Google Scholar 

  14. P. Kirsh, Modern Fluoroorganic Chemistry (Synthesis, Reactivity Applications), 2nd ed., Wiley-VCH, Weinheim, 2013, 384 pp.

    Google Scholar 

  15. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Eds A. Padwa, W. H. Pearson, Wiley, New Jersey, 2003, 940 pp.

    Google Scholar 

  16. G. Cremonesi, P. D. Croce, F. Fontana, C. Fiorelli, C. La Rosa, Tetrahedron: Asymmetry, 2008, 19, 2850.

    Article  Google Scholar 

  17. P. Tarrant, R. E. Taylor, J. Org. Chem., 1959, 24, 238.

    Article  Google Scholar 

  18. J. V. Kazennikova, T. V. Talalaeva, A. V. Zimin, K. A. Kocheshkov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1961, 10, 985.

    Article  Google Scholar 

  19. B. M. Trost, L. Debien, J. Am. Chem. Soc., 2015, 137, 11606.

    Article  Google Scholar 

  20. T. Fujita, M. Takazawa, K. Sugiyama, N. Suzuki, J. Ichikawa, Org. Lett., 2017, 19, 588.

    Article  Google Scholar 

  21. D. Dolenc, B. Plesnicar, J. Org. Chem. 2006, 71, 8028.

    Article  Google Scholar 

  22. S. N. Osipov, A. S. Golubev, D. V. Vorob´eva, I. E. Yagafarova, T. P. Vasil´eva, Yu. Ya. Spiridonov, L. D. Protasova, N. D. Chkanikov, Agrokhimiya [Agrochemistry], 2016, 10, 57 (in Russian).

    Google Scholar 

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    A. L. Sigan, A. S. Golubev, E. V. Belyaeva, S. M. Gorfinkel, N. D. Kagramanov & N. D. Chkanikov

  2. All-Russian Research Institute of Phytopathology, 5 ul. Institut, 143050, Bol′shie Vyazemy, Moscow Region, Russian Federation

    Yu. Ya. Spiridonov

Authors
  1. A. L. Sigan
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  2. A. S. Golubev
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  3. E. V. Belyaeva
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  4. S. M. Gorfinkel
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  5. N. D. Kagramanov
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  6. Yu. Ya. Spiridonov
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  7. N. D. Chkanikov
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Corresponding authors

Correspondence to A. L. Sigan or Yu. Ya. Spiridonov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0099–0103, January, 2019.

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Sigan, A.L., Golubev, A.S., Belyaeva, E.V. et al. Synthesis of ethyl 5-aryl-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-carboxylates, exhibiting plant growth-regulating properties. Russ Chem Bull 68, 99–103 (2019). https://doi.org/10.1007/s11172-019-2422-6

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  • DOI: https://doi.org/10.1007/s11172-019-2422-6

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