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Synthesis of 6-hydroxy-5,6-dihydro-2-pyrones and -pyridones by reaction of 4-aryl-6-trifluoromethyl-2-pyrones with water, hydrazine, and hydroxylamine

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Chemistry of Heterocyclic Compounds Aims and scope

Reactions of 4-aryl-6-trifluoromethyl-2H-pyran-2-ones with sodium hydroxide followed by acidification provided the respective 6-hydroxy-5,6-dihydro derivatives, while the reactions of 4-aryl-6-trifluoromethyl-2H-pyran-2-ones with hydrazine and hydroxylamine were accompanied by rearrangement to N-substituted 6-hydroxy-5,6-dihydro-2-pyridones.

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References

  1. (a) Hänsel, R.; Pelrer, A.; Schulz, J.; Hille, C. Chem. Ber. 1976, 109, 1617. (b) Hänsel, R.; Schulz, J. Arch. Pharm. 1982, 315, 147.

  2. Nicotra, V. E.; Ramacciotti, N. S.; Gil, R. R.; Oberti, J. C.; Feresin, G. E.; Guerrero, C. A.; Baggio, R. F.; Garland, M. T.; Burton G. J. Nat. Prod. 2006, 69, 783.

    Article  CAS  Google Scholar 

  3. (a) Nahrstedt, A.; Kant, J.-D.; Wray, V. Phytochem. 1982, 21, 101. (b) Hungeling, M.; Lechtenberg, M.; Fronczek, F. R.; Nahrstedt, A. Phytochem. 2009, 70, 270.

  4. Ito, K.; Miyajima, S. Bull. Chem. Soc. Jpn. 1986, 59, 815.

    Article  CAS  Google Scholar 

  5. (a) Caspi, E.; Schmid, W.; Khan, B. T. Tetrahedron 1962, 18, 767. (b) Kocór, M.; Kurek, A.; Dabrowski, J. Tetrahedron 1969, 25, 4257. (c) Frimer, A. A.; Ripstos, S.; Marks, V.; Aljadeff, G.; Hameiri-Buch J.; Gilinsky-Sharon, P. Tetrahedron 1991, 47, 8361. (d) Frimer, A. A.; GilinskySharon, P.; Aljadeff, G.; Gottlieb, H. E.; Hameiri-Buch, J.; Marks, V.; Philosof, R.; Rosental, Z. J. Org. Chem. 1989, 54, 4853. (e) Frimer, A. A.; Gilinsky-Sharon, P.; Aljadeff, G.; Marks, V.; Rosental, Z. J. Org. Chem. 1989, 54, 4866. (f) Frimer, A. A.; Gilinsky-Sharon, P.; Aljadeff, G. Tetrahedron Lett. 1982, 23, 1301. (g) Srinivasan, R.; Rinehart, K., Jr. J. Org. Chem. 1968, 33, 351. (h) Miyajima, S.; Ito, K. Bull. Chem. Soc. Jpn. 1985, 58, 2659. (i) Padwa, A.; Eisenbarth, P. Tetrahedron 1985, 41, 283. (j) Langer, J.; Fischer, R.; Görls, H.; Walther, D. J. Organomet. Chem. 2004, 689, 2952.

  6. Yamada, K.; Naito, T.; Okuhara, K.; Nakata, K.; Hirata, Y. Bull. Chem. Soc. Jpn. 1960, 33, 1303.

    Article  CAS  Google Scholar 

  7. (a) Zonov, Y. V.; Karpov, V. M.; Platonov. V. E. J. Fluorine Chem. 2007, 128, 1065. (b) Zonov, Y. V.; Karpov, V. M.; Platonov, V. E. Russ. J. Org. Chem. 2010, 46, 1517. [Zh. Org. Khim. 2010, 46, 1512.]

  8. (a) Gerus, I. I.; Tolmachova, N. A.; Vdovenko, S. I.; Fröhlich, R.; Haufe, G. Synthesis 2005, 1269. (b) Tolmachova, N. A.; Dolovanyuk, V. G.; Gerus, I. I.; Kondratov, I. S.; Polovinko, V. V.; Bergander, K.; Haufe G. Synthesis 2011, 1149.

  9. Modyanova, L.; Azerad, R. Tetrahedron Lett. 2000, 41, 3865.

    Article  CAS  Google Scholar 

  10. Shone, R. L. Tetrahedron Lett. 1979, 24, 2185.

    Article  Google Scholar 

  11. (a) Usachev, B. I.; Obydennov, D. L.; Röschenthaler, G.-V.; Sosnovskikh, V. Y. Org. Lett. 2008, 10, 2857. (b) Usachev, S. A.; Usachev, B. I.; Sosnovskikh, V. Y. Tetrahedron 2014, 70, 60. (с) Usachev, S. A.; Usachev, B. I.; Eltsov, O. S.; Sosnovskikh, V. Y. Tetrahedron 2014, 70, 8863. (d) Usachev, S. A.; Popova, N. V.; Moshkin, V. S.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2015, 51, 913. [Khim. Geterotsikl. Soedin. 2015, 51, 913.]

  12. Yeh, P.-P.; Daniels, D. S. B.; Cordes, D. B.; Slawin, A. M. Z.; Smith, A. D. Org. Lett. 2014, 16, 964.

    Article  CAS  Google Scholar 

  13. Peet, N. P.; Sunder, S. Heterocycles 1986, 24, 393.

    Article  CAS  Google Scholar 

  14. (a) Shusherina, N. P.; Dmitrieva, N. D.; Luk'yanets, E. A.; Levina, R. Ya. Russ. Chem. Rev. 1967, 36, 175. [Usp. Khim. 1967, 36, 437.] (b) Phillips, A. J.; Henderson, J. A.; Jackson, K. L. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Amsterdam, 2008, Vol. 7, p. 366. (с) Goel, A.; Ram, V. J. Tetrahedron 2009, 65, 7865.

  15. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

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This work was performed with financial support from the Russian Foundation for Basic Research (grant No. 1703-00340).

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Authors and Affiliations

  1. Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg, 620000, Russia

    Sergey A. Usachev & Vyacheslav Ya. Sosnovskikh

  2. Department of Chemistry, School of Pure Sciences, College of Engineering, Science & Technology, Fiji National University, P.O. Box 5529, Lautoka, Fiji

    Boris I. Usachev

Authors
  1. Sergey A. Usachev
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  2. Boris I. Usachev
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  3. Vyacheslav Ya. Sosnovskikh
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Correspondence to Sergey A. Usachev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(12), 1294–1301

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Usachev, S.A., Usachev, B.I. & Sosnovskikh, V.Y. Synthesis of 6-hydroxy-5,6-dihydro-2-pyrones and -pyridones by reaction of 4-aryl-6-trifluoromethyl-2-pyrones with water, hydrazine, and hydroxylamine. Chem Heterocycl Comp 53, 1294–1301 (2017). https://doi.org/10.1007/s10593-018-2209-y

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  • DOI: https://doi.org/10.1007/s10593-018-2209-y

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