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SN H reactions of 3-fluoronitroarenes with chloromethyl sulfone as the method for the construction of 6-fluoro-3-sulfonylindoles

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Abstract

5-R-6-Fluoro-3-phenylsulfonylindoles were synthesized by the SN H reaction of 3-fluoronitrobenzenes with chloromethyl phenyl sulfone in DMSO in the presence of KOH with subsequent reduction of the nitro group and intramolecular cyclization of imidates.

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References

  1. O. N. Chupakhin, V. N. Charushin, and H. C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen, Academic Press, New York, 1994, 367 pp.

    Google Scholar 

  2. M. Makosza and K. Wojciechowski, Chem. Rev., 2004, 104, 2631.

    Article  CAS  Google Scholar 

  3. M. Makosza, Izv. Akad. Nauk, Ser. Khim., 1996, 531 [Russ. Chem. Bull., 1996, 45, 491 (Engl. Transl.)].

  4. W. Verboom, E. O. M. Orlemans, H. J. Berga, M. W. Scheltinga, and D. N. Reinhoudt, Tetrahedron, 1986, 42, 5053.

    Article  CAS  Google Scholar 

  5. K. R. Campos and J. S. Woo, Org. Lett., 2004, 6, 79.

    Article  CAS  Google Scholar 

  6. M. D. Mashkovskii, Lekarstvennye sredstva [Medicines], 1998, 1, 560 pp. (in Russian).

  7. M. D. Mashkovskii, Lekarstvennye sredstva [Medicines], 1998, 2, 592 pp. (in Russian).

  8. R. Silvestri and G. De Martino, J. Med. Chem., 2003, 46, 2482.

    Article  CAS  Google Scholar 

  9. J. M. Berry and T. D. Bradshow, J. Med. Chem., 2005, 48, 639.

    Article  CAS  Google Scholar 

  10. WO, 48,330 Al., Chem. Abstrs., 2004, 141, 38523r.

  11. WO, 11,284, Al., Chem. Abstrs., 2003, 138, 153437r.

  12. WO, 40,112, Al., Chem. Abstrs., 2005, 142, 463596u.

  13. K. Wojciechowski and M. Makosza, Synthesis, 1986, 651.

  14. K. Wojciechowski and M. Makosza, Tetrahedron Lett., 1984, 25, 4793.

    Article  CAS  Google Scholar 

  15. G. A. Zhumabaeva, S. K. Kotovskaya, N. M. Perova, V. N. Charushin, and O. N. Chupakhin, Izv. Akad. Nauk, Ser. Khim., 2006, 1196 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1243].

    Google Scholar 

  16. O. M. Nefedov, A. I. Ioffe, and L. G. Menchikov, Khimiya karbenov [Chemistry of Carbenes], Khimiya, Moscow, 1990, 256 pp. (in Russian).

    Google Scholar 

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Authors and Affiliations

  1. Urals State Technical University — UPI, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    G. A. Zhumabaeva, S. K. Kotovskaya, N. M. Perova, V. N. Charushin & O. N. Chupakhin

  2. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi/Akademicheskaya, 620041, Ekaterinburg, Russian Federation

    V. N. Charushin & O. N. Chupakhin

Authors
  1. G. A. Zhumabaeva
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  2. S. K. Kotovskaya
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  3. N. M. Perova
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  4. V. N. Charushin
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  5. O. N. Chupakhin
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Corresponding author

Correspondence to S. K. Kotovskaya.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1980–1984, October, 2007.

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Zhumabaeva, G.A., Kotovskaya, S.K., Perova, N.M. et al. SN H reactions of 3-fluoronitroarenes with chloromethyl sulfone as the method for the construction of 6-fluoro-3-sulfonylindoles. Russ Chem Bull 56, 2048–2053 (2007). https://doi.org/10.1007/s11172-007-0320-9

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  • DOI: https://doi.org/10.1007/s11172-007-0320-9

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