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Transformations of gem-dibromoarylcyclopropanes under nitrosation conditions on treatment with NOCl·(SO3) n

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Abstract

The reaction of 2-aryl-1,1-dibromocyclopropanes with adduct NOCl·(SO3) n leading to 3-aryl-5-bromoisoxazoles as a result of nitrosation—heterocyclization of the cyclopropane ring was studied. The reaction is accompanied with electrophilic aromatic bromination. The mechanism of the transformation was discussed, the optimal reaction conditions to enhance the reaction selectivity were developed.

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References

  1. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Eds A. de Meijere, F. Diederich, Wiley-VCH, Weinheim, 2004, 916 pp.

  2. M. Schnürch, R. Flasik, A. F. Khan, M. Spina, M. D. Mihovilovic, P. Stanetty, Eur. J. Org. Chem., 2006, 3283.

    Google Scholar 

  3. X. Huang, G. W. Shipps, Jr., C. C. Cheng, P. Spacciapoli, X. Zhang, M. A. McCoy, D. F. Wyss, X. Yang, A. Achab, K. Soucy, D. K. Montavon, D. M. Murphy, C. E. Whitehurst, ACS Med. Chem. Lett., 2011, 2, 632.

    Article  CAS  Google Scholar 

  4. P. Ratcliffe, L. Abernethy, N. Ansari, K. Cameron, T. Clarkson, M. Dempster, D. Dunn, A.-M. Easson, D. Edwards, K. Everett, H. Feilden, K.-K. Ho, S. Kultgen, P. Littlewood, J. Maclean, D. McArthur, D. McGregor, H. McLuskey, I. Neagu, O. Nimz, L.-A. Nisbet, M. Ohlmeyer, R. Palin, Q. Pham, Y. Rong, A. Roughton, M. Sammons, R. Swanson, H. Tracey, G. Walker, Bioorg. Med. Chem. Lett., 2011, 21, 4652.

    Article  CAS  Google Scholar 

  5. K. Takenaka, S. Nakatsuka, T Tsujihara, P. S. Koranne, H. Sasai, Tetrahedron: Asymmetry, 2008, 19, 2492.

    Article  CAS  Google Scholar 

  6. M. Shailaja, A. Manjula, R. B. Vittal, B. Praseeda, R. B. Madhava, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 2011, 50, 214.

    Google Scholar 

  7. R. Palin, L. Abernethy, N. Ansari, K. Cameron, T. Clarkson, M. Dempster, D. Dunn, A.-M. Easson, D. Edwards, J. Maclean, K. Everett, H. Feilden, K.-K. Ho, S. Kultgen, P. Littlewood, D. McArthur, D. McGregor, H. McLuskey, I. Neagu, S. Neale, L.-A. Nisbet, M. Ohlmeyer, Q. Pham, P. Ratcliffe, Y. Rong, A. Roughton, M. Sammons, R. Swanson, H. Tracey, G. Walker, Bioorg. Med. Chem. Lett., 2011, 21, 892.

    Article  CAS  Google Scholar 

  8. S. Sanders, V. Harisdangkul, Am. J. Med. Sci., 2002, 323, 190.

    Article  Google Scholar 

  9. P. Pinto, M. Dougados, Acta Reumatol. Port., 2006, 31, 215.

    Google Scholar 

  10. J. Kremer, M. Genovese, G. W. Cannon, J. Caldwell, J. Cush, D. Furst, M. Luggen, E. Keystone, J. Bathon, A. Kavanaugh, E. Ruderman, P. Coleman, D. Curtis, E. Kopp, S. Kantor, M. Weisman, J. Waltuck, H. B. Lindsley, J. Markenson, B. Crawford, I. Fernando, K. Simpson, V. Strand, J. Rheumatol., 2004, 31, 1521.

    CAS  Google Scholar 

  11. J. B. Carr, H. G. Durham, D. K. Hass, J. Med. Chem., 1977, 20, 934.

    Article  CAS  Google Scholar 

  12. Pat. US 3781438; http://patft.uspto.gov/netahtml/PTO/srchnum.htm.

  13. A. A. Vieira, F. R. Bryk, G. Conte, A. J. Bortoluzzi, H. Gallardo, Tetrahedron Lett., 2009, 50, 905.

    Article  CAS  Google Scholar 

  14. N. K. Kochetkov, S. D. Sokolov, N. M. Vagurtova, E. E. Nifantiev, Dokl. Akad. Nauk SSSR, 1960, 133, 598 (in Russian).

    CAS  Google Scholar 

  15. A. Quilico, R. Justoni, Rend. Ist. Lombardo Sci., 1936, 69, 439; Chem. Abstrs., 1938, 32, 7455.

    CAS  Google Scholar 

  16. G. Li, R. Kakarla, S. W. Gerritz, Tetrahedron Lett., 2007, 48, 4595.

    Article  CAS  Google Scholar 

  17. M. Iglesias, O. Schuster, M. Albrecht, Tetrahedron Lett., 2010, 51, 5423.

    Article  CAS  Google Scholar 

  18. F. J. Vinick, Y. Pan, H W. Gschwend, Tetrahedron Lett., 1978, 19, 422l.

    Google Scholar 

  19. U. Schöllkopt, I. Hoppe, Angew. Chem., Int. Ed., 1975, 14, 765.

    Article  Google Scholar 

  20. G. Adembri, P. Tedeschi, Boll. Sci. Fac. Chim. Ind. Bologna, 1965, 23, 203.

    CAS  Google Scholar 

  21. S.-T. Lin, S.-H. Kuo, F.-M. Yang, J. Org. Chem., 1997, 62, 5229.

    Article  CAS  Google Scholar 

  22. W. E. Doering, A. K. Hoffmann, J. Am. Chem. Soc., 1954, 76, 6162.

    Article  CAS  Google Scholar 

  23. M. Mąkosza M. Wawrzyniewicz, Tetrahedron Lett., 1969, 4659.

    Google Scholar 

  24. O. B. Bondarenko, A. Yu. Gavrilova, L. G. Saginova, N. V. Zyk, N. S. Zefirov, Russ. Chem. Bull. (Int. Ed.), 2003, 52, 778 [Izv. Akad. Nauk, Ser. Khim., 2003, 741].

    Article  CAS  Google Scholar 

  25. R. C. Paul, C. L. Arora, K. C. Malhotra, Indian J. Chem., 1972, 10, 92.

    CAS  Google Scholar 

  26. O. B. Bondarenko, A. Yu. Gavrilova, M. A. Kazantseva, V. N. Tikhanushkina, E. E. Nifant´ev, L. G. Saginova, N. V. Zyk, Russ. J. Org. Chem. (Engl. Transl.), 2007, 43, 564 [Zh. Org. Khim., 2007, 43, 566].

    Article  CAS  Google Scholar 

  27. N. V. Zyk, O. B. Bondarenko, A. Yu. Gavrilova, A. O. Chizhov, N. S. Zefirov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 328 [Izv. Akad. Nauk, Ser. Khim., 2011, 321].

    Article  CAS  Google Scholar 

  28. O. B. Bondarenko, A. Yu. Gavrilova, D. S. Murodov, N. V. Zyk, N. S. Zefirov, Russ. J. Org. Chem. (Engl. Transl.), 2013, 49, 186 [Zh. Org. Khim., 2013, 49, 198].

    Article  CAS  Google Scholar 

  29. M. Sutharchanadevi, R. Murugan, in Comprehensive Heterocyclic Chemistry II, Second Edition: A Review of the Literature 1982–1995, Eds A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Vol. 3, Five-membered Rings with Two Heteroatoms and Fused Carbocyclic Derivatives, Elsevier Sci. Ltd., 1996, pp. 226–227.

  30. G. C. Levy, G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, J. Wiley and Sons, Chichester, 1972.

    Google Scholar 

  31. F. Radner, Acta Chem. Scand., 1989, 43, 902.

    Article  CAS  Google Scholar 

  32. O. B. Bondarenko, A. A. Vinogradov, P. A. Danilov, S. N. Nikolaeva, A. Yu. Gavrilova, N. V. Zyk, Tetrahedron Lett., 2015, 56, 6577.

    Article  CAS  Google Scholar 

  33. A. Gordon, R. Ford, The Chemist´s Companion: A Handbook of Practical Data, Techniques, and References, Wiley, New York, 1972, 560 pp.

    Google Scholar 

  34. S.-T. Lin, M.-L. Lin, J. Chem. Soc., Perkin Trans. 2, 1990, 91.

    Google Scholar 

  35. V. D. Novokreshchenych, S. S. Mochalov, Yu. S. Shabarov, J. Org. Chem. URSS [Zh. Org. Khim.], 1979, 15, 485 (in Russian).

    Google Scholar 

  36. Bruker SADABS, version 2008/1, Bruker AXS, Madison, (WI).

  37. G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3.

    Article  Google Scholar 

  38. F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci., 2002, 58, 380.

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119992, Moscow, Russian Federation

    O. B. Bondarenko, A. Yu. Gavrilova, S. N. Nikolaeva & N. V. Zyk

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432, Russian Federation

    N. V. Zyk

Authors
  1. O. B. Bondarenko
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  2. A. Yu. Gavrilova
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  3. S. N. Nikolaeva
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  4. N. V. Zyk
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Correspondence to O. B. Bondarenko.

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Dedicated to Academician of the Russian Academy of Sciences O. G. Sinyashin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1225–1231, May, 2016.

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Bondarenko, O.B., Gavrilova, A.Y., Nikolaeva, S.N. et al. Transformations of gem-dibromoarylcyclopropanes under nitrosation conditions on treatment with NOCl·(SO3) n . Russ Chem Bull 65, 1225–1231 (2016). https://doi.org/10.1007/s11172-016-1439-3

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  • DOI: https://doi.org/10.1007/s11172-016-1439-3

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