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The rearrangement of trifluoroacetylchromenes to trifluoromethylchromenols

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of o-phenylenediamine with condensed 4H-pyrans containing a trifluoroacetyl group at the β-position relative to the oxygen atom led to 2-(trifluoromethyl)chroman-2-ols and 3-(trifluoromethyl)-2,3-dihydro-1H-benzo[f]chromen-3-ols via a cascade process that was initiated by a Michael reaction.

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References

  1. Bassetto, M.; Ferla, S.; Pertusati, F. Future Med. Chem. 2015, 7, 527.

    Article  CAS  Google Scholar 

  2. (a) Schütz, H. Benzodiazepines: A Handbook. Basic Data, Analytical Methods, Pharmacokinetics and Comprehensive Literature; Springer-Verlag: Heidelberg, 1982. (b) Schütz, H. Benzodiazepines II: A Handbook. Basic Data, Analytical Methods, Pharmacokinetics and Comprehensive Literature; Springer-Verlag: Berlin, Heidelberg, 1989.

  3. Mkrtchyan, E. G.; Yachevskii, D. S.; Chizhov, D. L.; Charushin, V. N. Russ. Chem. Bull., Int. Ed. 2005, 54, 2150. [Izv. Akad. Nauk, Ser. Khim. 2005, 2086.]

  4. Kudyakova, Yu. S.; Goryaeva, M. V.; Burgart, Ya. V.; Slepukhin, P. A.; Saloutin, V. I. Russ. Chem. Bull., Int. Ed. 2010, 59, 1582. [Izv. Akad. Nauk, Ser. Khim. 2010, 1544.]

  5. Chopin, N.; Médebielle, M.; Pilet, G. Eur. J. Inorg. Chem. 2012, 1093.

  6. Gerus, I. I.; Gorbunova, M. G.; Vdovenko, S. I.; Yagupol'skii, Yu. L.; Kukhar', V. P. J. Org. Chem. USSR 1990, 26, 1623. [Zh. Org. Khim. 1990, 26, 1877.]

  7. Chu, Q.; Wang, Y.; Zhu, S. Synth. Commun. 2000, 30, 677.

    Article  CAS  Google Scholar 

  8. Narsaiah, B.; Sivaprasad, A.; Venkataratnam, R. V. J. Fluorine Chem. 1994, 66, 47.

    Article  CAS  Google Scholar 

  9. Ota, N.; Okada, E.; Terai, N.; Miyamura, T.; Shibata, D.; Sakai, T. Heterocycles 2009, 77, 983.

    Article  CAS  Google Scholar 

  10. Chandra Sheker Reddy, A.; Shanthan Rao, P.; Venkataratnam, R.V. Tetrahedron 1997, 53, 5847.

    Article  Google Scholar 

  11. Ota, N.; Tomoda, T.; Terai, N.; Kamitori, Y.; Shibata, D.; Médebielle, M.; Okada, E. Heterocycles 2008, 76, 1205.

    Article  CAS  Google Scholar 

  12. Mamat, C.; Hein, M.; Miethchen, R. Carbohydr. Res. 2006, 341, 1758.

    Article  CAS  Google Scholar 

  13. Chandra Sheker Reddy, A.; Shanthan Rao, P.; Venkataratnam, R. V. Tetrahedron Lett. 1996, 37, 2845.

    Article  Google Scholar 

  14. Bonacorso, H. G.; Marques, L. M. L.; Zanatta, N.; Martins, M. A. P. Synth. Commun. 2002, 32, 3225.

    Article  CAS  Google Scholar 

  15. Roupany, A. J. A.; Baker, J. R. RSC Adv. 2013, 3, 10650.

    Article  CAS  Google Scholar 

  16. Lim, S.-G.; Jun, C.-H. Bull. Korean Chem. Soc. 2004, 25, 1623.

    Article  CAS  Google Scholar 

  17. Fan, H.-F.; Wang, X.-W.; Zhao, J.-W.; Li, X.-J.; Gao, J.-M.; Zhu, S.-Z. Synth. Commun. 2013, 43, 2883.

    Article  CAS  Google Scholar 

  18. Bonacorso, H. G.; Porte, L. M. F.; Cechinel, C. A.; Paim, G. R.; Deon, E. D.; Zanatta, N.; Martins, M. A. P. Tetrahedron Lett. 2009, 50, 1392.

    Article  CAS  Google Scholar 

  19. Bonacorso, H. G.; Cechinel, C. A.; Navarini, J.; Andrighetto, R.; Martins, M. A. P.; Zanatta, N. Monatsh. Chem. 2011, 142, 277.

    Article  CAS  Google Scholar 

  20. Osyanin, V. A. Dr. Chem. Sci. Theses, Samara, 2014. [http://d21221705.samgtu.ru/sites/d21221705.samgtu.ru/files/osyaninv.pdf]

  21. SDBSWeb: http://sdbs.db.aist.go.jp (National Institute of Advanced Industrial Science and Technology, date of access).

  22. Dreyer, D. R.; Jia, H.-P.; Todd, A. D.; Geng, J.; Bielawski, C. W. Org. Biomol. Chem. 2011, 9, 7292.

    Article  CAS  Google Scholar 

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The work was performed with financial support from the Ministry of Education and Science of the Russian Federation within the framework of the Project part of the State assignment for scientific activity (4.1597.2014/К) and the Grant Council of the President of the Russian Federation for support of young Russian scientists (grant MD-5833.2016.3).

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Correspondence to Vitaly A. Osyanin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(8), 559–563

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Osyanin, V.A., Popova, Y.V., Sakhnenko, D.V. et al. The rearrangement of trifluoroacetylchromenes to trifluoromethylchromenols. Chem Heterocycl Comp 52, 559–563 (2016). https://doi.org/10.1007/s10593-016-1931-6

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  • DOI: https://doi.org/10.1007/s10593-016-1931-6

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