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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 12, pp 1350–1361 | Cite as

Domino reaction of (2-haloethyl)polyfluorophenyl sulfides, sulfoxides, and sulfones with ammonia or amines: one-pot synthesis of 3,4-dihydro-2H-1,4-benzothiazines polyfluorinated at the benzene ring and the corresponding 1-oxides and 1,1-dioxides

  • Andrey S. KondratyevEmail author
  • Vitalij D. Shteingarts
  • Vladimir V. Litvak
  • Evgeny V. Tretyakov
  • Alexey V. Tkachev
Article

5,7,8-Trifluoro-3,4-dihydro-2H-1,4-benzothiazine, corresponding 1-oxide and 1,1-dioxide, as well as some of their 4- and 6-substituted derivatives were prepared in 39–88% yields via the reaction of ammonia or primary aliphatic amines with (2-haloethyl)-2,3,5,6-tetrafluorophenyl sulfides, sulfoxides, or sulfones. Formation of the heterocyclic moiety was shown to proceed as a two-stage process starting from halogen replacement at the side chain followed by intramolecular aminodefluorination. The ratio of the reaction rates of the two processes depends on the nature of the reagent used. Chemical structures of the cyclization products were proved by precise analysis of the NMR spectra and by comparing the experimental NMR parameters with those calculated by an empirical additivity scheme and quantum chemistry methods (DFT).

Keywords

ammonia 1,4-benzothiazine polyfluoroarenes domino reaction heterocyclization intramolecular aromatic nucleophilic substitution primary amines tandem reaction 

Notes

The research described was supported in part by the Russian Foundation for Basic Research (grant No. 14-03-00108 А). The authors thank the Chemical Service Center, SB RAS, Novosibirsk, for recording spectra of the compounds described and the Information Technology Centre of the Novosibirsk State University for providing access to the cluster computational resources to carry out quantumchemical calculations.

References

  1. 1.
    Fringuelli, R.; Milanese, L.; Schiaffella, F. Mini-Rev. Med. Chem. 2005, 5, 1061.CrossRefGoogle Scholar
  2. 2.
    Ajani, O. O. Arch. Pharm. 2012, 345, 841.CrossRefGoogle Scholar
  3. 3.
    Gupta, R. R.; Ojha, K. C. In Phenothiazines and 1,4-Benzothiazines – Chemical and Biochemical Aspects, Gupta, R. R., Ed.; Elsevier: Amsterdam, 1988, p. 163.Google Scholar
  4. 4.
    (a) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L., Eds.; Elsevier: Amsterdam, 1993. (b) Organofluorine Chemistry. Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (c) Davis, R.; Bryson, H. M. Drugs 1994, 47, 677. (d) Furin, G. G. Fluorine-containing Heterocyclic Compounds [in Russian]; Nauka: Novosibirsk, 2001, p. 9.Google Scholar
  5. 5.
    Armenise, D.; Muraglia, M.; Florio, M. A.; De Laurentis, N.; Rosato, A.; Carrieri, A.; Corbo, F.; Franchini, C. Arch. Pharm. 2012, 345, 407.CrossRefGoogle Scholar
  6. 6.
    Vysokov, V. I.; Charushin, V. N.; Chupakhin, O. N.; Pashkevich, T. K. Zh. Org. Khim. 1998, 34, 455.Google Scholar
  7. 7.
    Culbertson, T. P. J. Heterocycl. Chem. 1991, 28, 1701.Google Scholar
  8. 8.
    Cecchetti, V.; Fravolini, A.; Schiafella, F.; Tabarrini, O.; Zhou, W.; Pagella, P. G. J. Heterocycl. Chem. 1992, 29, 375.CrossRefGoogle Scholar
  9. 9.
    (a) Gupta, R. R.; Kumar, R.; Gautam, R. K. J. Fluorine Chem. 1985, 28, 381. (b) Gupta, R. R.; Thomas, A.; Gautam, R. K.; Gupta, V. J. Fluorine Chem. 1989, 44, 1. (c) Hamadi, M. Y.; Gupta, R.; Gupta, R. R. J. Fluorine Chem. 1999, 94, 169.Google Scholar
  10. 10.
    (a) Yakobson, G. G.; Petrova, T. D.; Kobrina, L. S. In Fluorine Chemistry Reviews; Tarrant, P., Ed.; Marcel Dekker: New York, 1974, vol. 7, p. 115. (b) Nosova, E. V.; Lipunova, G. N.; Charushin, V. N.; Chupakhin, O. N. J. Fluorine Chem. 2010, 131, 1267. (c) Hargreaves, C. A.; Sandford, G.; Slater, R.; Yufit, D. S.; Howard, J. A. K.; Vong, A. Tetrahedron 2007, 63, 5204. (d) Cargill, M. R.; Linton, K. E.; Sandford, G.; Yufit, D. S.; Howard, J. A. K. Tetrahedron 2010, 66, 2356. (e) Ranjbar-Karimi, R.; Mousavi, M. J. Fluorine Chem. 2010, 131, 587.Google Scholar
  11. 11.
    Amosova, S. V.; Gostevskaya, V. I.; Gavrilova, G. M.; Nesterov, V. N.; Struchkov, Yu. T.; Il’icheva, L. N. Chem. Heterocycl. Compd. 1996, 32, 1023. [Khim. Geterotsikl. Soedin. 1996, 1195.]CrossRefGoogle Scholar
  12. 12.
    Amosova, S. V.; Gavrilova, G. M.; Gostevskaya, V. I.; Afonin, A. V.; Larina, L. I. Chem. Heterocycl. Compd. 1998, 34, 625. [Khim. Geterotsikl. Soedin. 1998, 706.]CrossRefGoogle Scholar
  13. 13.
    (a) Bernotas, R. C., Dooley, R. J. Tetrahedron 2010, 66, 2273. (b) Parai, M. K.; Panda, G. Tetrahedron Lett. 2009, 50, 4703.Google Scholar
  14. 14.
    (a) Langille, K. R.; Peach, M. E. J. Fluorine Chem. 1972, 1, 407. (b) Musial, B. C.; Peach, M. E. J. Fluorine Chem. 1976, 7, 427. (c) Testaferri, L.; Tingoli, M.; Tiecco, M. J. Org. Chem. 1980, 45, 4376. (d) Crowell, T. R.; Peach, M. E. J. Fluorine Chem. 1982, 21, 469. (e) MacNicol, D. D.; Mallison, P. R.; Murphy, A.; Sym, G. J. Tetrahedron Lett. 1982, 23, 4131. (f) Pastor, S. D.; Hessell, E. T. J. Org. Chem. 1985, 50, 4812.Google Scholar
  15. 15.
    Kizner, T. A.; Shteingarts, V. D. Zh. Org. Khim. 1989, 25, 2424.Google Scholar
  16. 16.
    Litvak, V. V.; Kondrat'ev, A. S.; Shteingarts, V. D. Russ. J. Org. Chem. 2009, 45, 1637. [Zh. Org. Khim. 2009, 45, 1648.]CrossRefGoogle Scholar
  17. 17.
    Krulikovskaya, E. A.; Dozmorov, S. V. Zh. Obshch. Khim. 1972, 42, 2248.Google Scholar
  18. 18.
    (a) González, J. P.; Edgar, M.; Elsegood, M. R. J.; Weaver, G. W. Org. Biomol. Chem. 2011, 9, 2294. (b) Kolchina, E. F. Dis. kand. khim. nauk; Novosibirsk, 2004.Google Scholar
  19. 19.
    Bruce, M. I. J. Chem. Soc. A 1968, 1459. Google Scholar
  20. 20.
    Pushkina, L. N.; Stepanov, A. P.; Zhukov, V. S.; Naumov, A. D. Zh. Org. Khim. 1972, 8, 586. Google Scholar
  21. 21.
    Sheppard, W. A.; Foster, S. S. J. Fluorine Chem. 1972, 2, 53.CrossRefGoogle Scholar
  22. 22.
    Marriott, J. H.; Moreno Barber, A. M.; Hardcastle, I. R.; Rowlands, M. G.; Grimshaw, R. M.; Neidle, S.; Jarman, M. J. Chem. Soc., Perkin Trans. 1 2000, 24, 4265.Google Scholar
  23. 23.
    Sandford, G.; Tadeusiak, A.; Yufit, D. S.; Howard, J. A. K. J. Fluorine Chem. 2007, 128, 1216.CrossRefGoogle Scholar
  24. 24.
    Petrova, T. D.; Savchenko, T. I.; Kukovinets, O. S.; Yakobson, G. G. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk. 1974, 2, 117.Google Scholar
  25. 25.
    Petrov, V. P.; Barkhash, V. A. Chem. Heterocycl. Compd. 1970, 6, 357. [Khim. Geterotsikl. Soedin. 1970, 385.]CrossRefGoogle Scholar
  26. 26.
    Konstantinova, A. V.; Gerasimova, T. N.; Kozlova, M. M.; Petrenko, N. I. Chem. Heterocycl. Compd. 1989, 25, 451. [Khim. Geterotsikl. Soedin. 1989, 539.]CrossRefGoogle Scholar
  27. 27.
    Gerasimova, T. N.; Kargapolova, I. Yu. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk. 1986, 5, 112.Google Scholar
  28. 28.
    Hogben, M. G.; Graham, W. A. G. J. Am. Chem. Soc. 1969, 91, 283.CrossRefGoogle Scholar
  29. 29.
    Abraham, R. J.; Macdonald, D. B.; Pepper, E. S. J. Am. Chem. Soc. 1968, 90, 147.CrossRefGoogle Scholar
  30. 30.
    Furin, G. G.; Yakobson, G. G. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk. 1977, 2, 109.Google Scholar
  31. 31.
    Furin, G. G., Yakobson, G. G. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk. 1976, 3, 120.Google Scholar
  32. 32.
    Andreevskaya, O. I.; Furin, G. G.; Yakobson, G. G. Zh. Org. Khim. 1977, 13, 1684.Google Scholar
  33. 33.
    Cohen, E. A.; Bourn, A. J. R.; Manatt, S. L. J. Magn. Reson. 1969, 1, 436.Google Scholar
  34. 34.
    Neese, F. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 73.Google Scholar
  35. 35.
    Dalton, a Molecular Electronic Structure Program, Release Dalton2015.0 (2015); http://daltonprogram.org
  36. 36.
    Aidas, K.; Angeli, C.; Bak, K. L.; Bakken, V.; Bast, R.; Boman, L.; Christiansen, O.; Cimiraglia, R.; Coriani, S.; Dahle, P.; Dalskov, E. K.; Ekström, U.; Enevoldsen, T.; Eriksen, J. J.; Ettenhuber, P.; Fernández, B.; Ferrighi, L.; Fliegl, H.; Frediani, L.; Hald, K.; Halkier, A.; Hättig, C.; Heiberg, H.; Helgaker, T.; Hennum, A. C.; Hettema, H.; Hjertenæs, E.; Høst, S.; Høyvik, I.-M.; Iozzi, M. F.; Jansik, B.; Jensen, H. J. Aa.; Jonsson, D.; Jørgensen, P.; Kauczor, J.; Kirpekar, S.; Kjærgaard, T.; Klopper, W.; Knecht, S.; Kobayashi, R.; Koch, H.; Kongsted, J.; Krapp, A.; Kristensen, K.; Ligabue, A.; Lutnæs, O. B.; Melo, J. I.; Mikkelsen, K. V.; Myhre, R. H.; Neiss, C.; Nielsen, C. B.; Norman, P.; Olsen, J.; Olsen, J. M. H.; Osted, A.; Packer, M. J.; Pawlowski, F.; Pedersen, T. B.; Provasi, P. F.; Reine, S.; Rinkevicius, Z.; Ruden, T. A.; Ruud, K.; Rybkin, V.; Salek, P.; Samson, C. C. M.; Sánchez de Merás, A.; Saue, T.; Sauer, S. P. A.; Schimmelpfennig, B.; Sneskov, K.; Steindal, A. H.; Sylvester-Hvid, K. O.; Taylor, P. R.; Teale, A. M.; Tellgren, E. I.; Tew, D. P.; Thorvaldsen, A. J.; Thøgersen, L.; Vahtras, O.; Watson, M. A.; Wilson, D. J. D.; Ziolkowski, M.; Ågren, H. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2014, 4, 269.Google Scholar
  37. 37.
    Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.CrossRefGoogle Scholar
  38. 38.
    Ovenall, D. W.; Chang, J. J. J. Magn. Reson. 1977, 25, 361.Google Scholar

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Authors and Affiliations

  • Andrey S. Kondratyev
    • 1
    Email author
  • Vitalij D. Shteingarts
    • 1
  • Vladimir V. Litvak
    • 2
  • Evgeny V. Tretyakov
    • 1
    • 3
  • Alexey V. Tkachev
    • 1
    • 3
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussia
  2. 2.Institute of Chemical Biology and Fundamental MedicineSiberian Branch of the Russian Academy of SciencesNovosibirskRussia
  3. 3.Novosibirsk State UniversityNovosibirskRussia

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