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Preparation of benzisothiazolones from 2-bromobenzamides and sulfur under copper catalysis conditions

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Chemistry of Heterocyclic Compounds Aims and scope

A convenient two-stage method has been developed for preparing benz[d]isothiazol-3(2H)-ones from 2-bromobenzamides and sulfur in a one-pot process under copper catalysis conditions. The method is suitable for the synthesis of N-aryl-, benzyl-, and alkyl-substituted benzisothiazolones. The yields of the benzisothiazolones depend on the nature of the starting amide and can reach 91%.

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References

  1. D. Dou, D. Alex, B. Du, K.-C. Tiew, S. Aravapalli, S. R. Mandadapu, R. Calderone, and W. C. Groutas, Bioorg. Med. Chem., 19, 5782 (2011).

    Article  CAS  Google Scholar 

  2. T. T. Slawik, Pharmazie, 46, 777 (1991).

    CAS  Google Scholar 

  3. J. A. Loo, T. P. Holler, J. Sanchez, R. Gogliotti, L. Maloney, and M. D. Reily, J. Med. Chem., 39, 4313 (1996).

    Article  CAS  Google Scholar 

  4. P. Vicini, M. Incerti, P. La Colla, and R. Loddo, Eur. J. Med. Chem., 44, 1801 (2009).

    Article  CAS  Google Scholar 

  5. S. Ranganathan, K. M. Muraleedharan, P. Bharadwaj, D. Chatterji, and I. Karle, Tetrahedron, 58, 2861 (2002).

    Article  CAS  Google Scholar 

  6. S. W. Wright, J. J. Petraitis, M. M. Abelman, L. L. Bostrom, R. L. Corbett, A. M. Green, R. M. Kindt, S. R. Sherk, and R. L. Magolda, Bioorg. Med. Chem. Lett., 3, 2875 (1993).

    Article  CAS  Google Scholar 

  7. B. K. Sarma and G. Mugesh, J. Am. Chem. Soc., 129, 8872 (2007).

    Article  CAS  Google Scholar 

  8. G. Brahemi, F. R. Kona, A. Fiasella, D. Buac, J. Soukupova, A. Brancale, A. M. Burger, and A. D Westwell, J. Med. Chem., 53, 2757 (2010).

    Google Scholar 

  9. R. Dahl, Y. Bravo, V. Sharma, M. Ichikawa, R.-P. Dhanya, M. Hedrick, B. Brown, J. Rascon, M. Vicchiarelli, A. Mangravita-Novo, L. Yang, D. Stonich, Y. Su, L. H. Smith, E. Sergienko, H. H. Freeze, and N. D. P. Cosford, J. Med. Chem., 54, 3661 (2011).

    Article  CAS  Google Scholar 

  10. M. Shimizu, T. Shimazaki, T. Yoshida, W. Ando, and T. Konakahara, Tetrahedron, 68, 3932 (2012).

    Article  CAS  Google Scholar 

  11. G. Pinna, M. C. Bellucci, L. Malpezzi, L. Pisani, S. Superchi, A. Volonterio, and M. Zanda, Tetrahedron, 67, 5268 (2011).

    Article  CAS  Google Scholar 

  12. T. Sano, T. Takagi, Y. Gama, I. Shibuya, and M. Shimizu, Synthesis, 1585 (2004).

  13. J. A. Turpin, Y. Song, J. K. Inman, M. Huang, A. Wallqvist, A. Maynard, D. G. Covell, W. G. Rice, and E. Appella, J. Med. Chem., 42, 67 (1999).

    Article  CAS  Google Scholar 

  14. K. H. Baggaley, P. D. English, L. J. A. Jennings, B. Morgan, B. Nunn, A. William, and R. Tyrrell, J. Med. Chem., 28, 1661 (1985).

    Article  CAS  Google Scholar 

  15. N. Kamigata, S. Hashimoto, M. Kobayashi, and H. Nakanishi, Bull. Chem. Soc. Jpn., 58, 3131 (1985).

    Article  CAS  Google Scholar 

  16. L. Katz and W. Schroeder, J. Org. Chem., 19, 103 (1954).

    Article  CAS  Google Scholar 

  17. J. P. Yevich, J. S. New, D. W. Smith, W. G. Lobeck, J. D. Catt, J. L. Minielli, M. S. Eison, D. P. Taylor, L. A. Riblet, and D. L. Temple, Jr., J. Med. Chem., 29, 359 (1986).

    Article  CAS  Google Scholar 

  18. C. K. Jin, J.-K. Moon, W. S. Lee, and K. S. Nam, Synlett, 1967 (2003).

  19. Y. Jiang, Y. Qin, S. Xie, X. Zhang, J. Dong, and D. Ma, Org. Lett., 11, 5250 (2009).

    Article  CAS  Google Scholar 

  20. H.-J. Xu, Y.-F. Liang, Z.-Y. Cai, H.-X. Qi, C.-Y. Yang, and Y.-S. Feng, J. Org. Chem., 76, 2296 (2011).

    Article  CAS  Google Scholar 

  21. N. Taniguchi, Synlett, 1687 (2005).

  22. C. Chen, Y. Xie, L. Chu, R.-W. Wang, X. Zhang, and F.-L. Qing, Angew. Chem., Int. Ed., 51, 2492 (2012).

  23. S. J. Balkrishna, B. S. Bhakuni, D. Chopra, and S. Kumar, Org. Lett., 12, 5394 (2010).

    Article  CAS  Google Scholar 

  24. B. S. Bhakuni, S. J. Balkrishna, A. Kumar, and S. Kumar, Tetrahedron Lett., 53, 1354 (2012).

    Article  CAS  Google Scholar 

  25. T. Furuta, Y. Kitamura, A. Hashimoto, S. Fujii, K. Tanaka, and T. Kan, Org. Lett., 9, 183 (2007).

    Article  CAS  Google Scholar 

  26. M. Shimizu, A. Takeda, H. Fukazawa, Y. Abe, and I. Shibuya, Heterocycles, 60, 1855 (2003).

    Article  CAS  Google Scholar 

  27. M. Shimizu, Y. Sugano, T. Konakahara, Y. Gama, and I. Shibuya, Tetrahedron, 58, 3779 (2002).

    Article  CAS  Google Scholar 

  28. I. Caleta, M. Kralj, M. Marjanovic, B. Bertosa, S. Tomic, G. Pavlovic, K. Pavelic, and G. Karminski-Zamola, J. Med. Chem., 52, 1744 (2009).

    Article  CAS  Google Scholar 

  29. G. Zhang, X. Zhao, Y. Yan, and C. Ding, Eur. J. Org. Chem., 669 (2012).

  30. P. Mangini, Gazz. Chim. Ital., 66, 337 (1936).

    CAS  Google Scholar 

  31. V. C. Agwada, J. Chem. Eng. Data, 27, 479 (1982).

    Article  CAS  Google Scholar 

  32. R. Campbell and C. J. Peterson, J. Org. Chem., 28, 2294 (1963).

    Article  CAS  Google Scholar 

  33. M. Hellal, and G. D. Cuny, Tetrahedron Lett., 52, 5508 (2011).

    Article  CAS  Google Scholar 

  34. 34 L. Donati, S. Michel, F. Tillequin, and F.-H. Poree, Org. Lett., 12, 156 (2010).

    Article  CAS  Google Scholar 

  35. M. Schwartz, NL Pat. Appl. 6407402.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga, LV-1006, Latvia

    V. Krasikova & M. Katkevics

Authors
  1. V. Krasikova
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  2. M. Katkevics
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Correspondence to M. Katkevics.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1800-1807, November, 2012.

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Krasikova, V., Katkevics, M. Preparation of benzisothiazolones from 2-bromobenzamides and sulfur under copper catalysis conditions. Chem Heterocycl Comp 48, 1684–1690 (2013). https://doi.org/10.1007/s10593-013-1193-5

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  • DOI: https://doi.org/10.1007/s10593-013-1193-5

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