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Synthesis of 2,1-benzisoxazoles (microreview)

  • HETEROCYCLES IN FOCUS
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Chemistry of Heterocyclic Compounds Aims and scope

This microreview summarizes data published over the past 10 years devoted to the synthesis of substituted 2,1-benzisoxazoles. The major synthetic approaches aim at increasing either the electrophilicity or nucleophilicity of ortho substituents or other substrates. Ortho-substituted aryl azides, anilines, nitroso- and nitrobenzenes were used as starting compounds.

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References

  1. (a) Wünsch, K.-H.; Boulton, A. J. In Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J., Eds.; Academic Press; New York, 1967, vVol. 8, p. 280. (b) Granik, V. G.; Pechenina, V. M.; Mukhina, N. A. Pharm. Chem. J. 1991, 25, 48. (c) Smalley, R. K. In Houben-Weyl, Methods in Organic Chemistry; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1992, Vol. E8a, p. 349. (d) Eswaran, S. V. In Chemistry of Heterocyclic Compounds: Isoxazoles; Griinanger, P., Vita-Finzi, P., Eds.; Dowling, J. E., Dev. Ed.; John Wiley & Sons. Inc, 1999; Part 2, Vol. 49, p. 123. (e) Kotov, A. D.; Prokaznikov, M. A.; Antonova, E. A.; Rusakov, A. I. Chem. Heterocycl. Compd. 2014, 50, 647. [Khim. Geterotsikl. Soedin. 2014, 704.]

  2. (a) Sadeghian, A.; Pordel, M.; Safdari, H.; Fahmidekar, M. A.; Sadeghian, H. Med. Chem. Res. 2012, 21, 3897. (b) Grimberg, B. T.; Jaworska, M. M.; Hough, L. B.; Zimmerman, P. A.; Phillips, J. G. Bioorg. Med. Chem. Lett. 2009, 19, 5452. (c) Kraus, J. M.; Tatipaka, H. B.; McGuffin, S. A.; Chennamaneni, N. K.; Karimi, M.; Arif, J.; Verlinde, C. L. M. J.; Buckner, F. S.; Gelb, M. H. J. Med. Chem. 2010, 53, 3887. (d) Li, Q.; Woods, K. W.; Wang, W.; Lin, N.-H.; Claiborne, A.; Gu, W. Z.; Cohen, J.; Stoll, V. S.; Hutchins, C.; Frost, D.; Rosenberg, S. H.; Sham, H. L. Bioorg. Med. Chem. Lett. 2005, 15, 2033.

  3. (a) Pierce, A. C.; Jacobs, M.; Stuver-Moody, C. J. Med. Chem. 2008, 51, 1972. (b) Parish, C. A.; Smith, S. K.; Calati, K.; Zink, D.; Wilson, K.; Roemer, T.; Jiang, B.; Xu, D.; Bills, G.; Platas, G.; Peláez, F.; Díez, M. T.; Tsou, N.; McKeown, A. E.; Ball, R. G.; Powles, M. A.; Yeung, L.; Liberator, P.; Harris, G. J. Am. Chem. Soc. 2008, 130, 7060. (c) McClay, K. R.; Steffan, R. J. US Patent 7973065. (d) Bräse, S.; Gläser, F.; Kramer, C. S.; Lindner, S.; Linsenmeier, A. M.; Masters, K.-S.; Meister, A. C.; Ruff, B. M.; Zhong, S. The Chemistry of Mycotoxins; Springer Science & Business Media, 2013, Vol. 97. (e) Purohit, S. S.; Veerapur V. P. Int. J. Pharm. Bio. Sci. 2012, 3(4), 142.

  4. (a) Lyssikatos, J. P.; Greca, S. D. L.; Yang, B. V. US Patent 6495564. (b) Massarotti, A.; Theeramunkong, S.; Mesenzani, O.; Caldarelli, A.; Genazzani, A. A.; Tron, G. C. Chem. Biol. Drug. Des. 2011, 78, 913.

  5. (a) Dzhons, D. Yu.; Budruev, A. V. Beilstein J. Org. Chem. 2016, 12, 874. (b) Sinjagina, D. Yu.; Budruev, A. V. High Energy Chem. 2013, 47, 162. [Khim. Vysokikh Energii 2013, 47, 275.]

  6. Stokes, B. J.; Vogel, C. V.; Urnezis, L. K.; Pan, M.; Driver, T. G. Org. Lett. 2010, 12, 2884.

    Article  CAS  Google Scholar 

  7. Mezhnev, V. V; Dutov, M. D.; Shevelev, S. A. Russ. Chem. Bull., Int. Ed. 2009, 58, 476. [Izv. Akad. Nauk, Ser. Khim. 2009, 466.]

  8. Golubev, A. S.; Shidlovskii, A. F.; Peregudov, A. S.; Kagramanov, N. D. Russ. Chem. Bull., Int. Ed. 2014, 63, 2264. [Izv. Akad. Nauk, Ser. Khim. 2014, 2264.]

  9. Yang, W.; Sun, J.; Xu, X.; Zhang, Q.; Liu, Q. Chem. Commun. 2014, 50, 4420.

    Article  CAS  Google Scholar 

  10. Gao, X.-A.; Yan, R.-L.; Wang, X.-X.; Yan, H.; Li, J.; Guo, H.; Huang, G.-S. J. Org. Chem. 2012, 77, 7700.

    Article  CAS  Google Scholar 

  11. Otley, K. D.; Ellman, J. A. J. Org. Chem. 2014, 79, 8296.

    Article  CAS  Google Scholar 

  12. Kasuga, N. C.; Saito, Y.; Okamura, N.; Miyazaki, T.; Satou, H.; Watanabe, K.; Ohta, T.; Morimoto, S.; Yamaguchi, K. J. Photochem. Photobiol. A Chem. 2016, 321, 41.

    Article  CAS  Google Scholar 

  13. (a) Cikotiene, I. Eur. J. Org. Chem. 2012, 2012, 2766. (b) Asao, N.; Sato, K.; Yamamoto, Y. Tetrahedron Lett. 2003, 44, 5675. (c) Patel, P.; Ramana, C. V. Org. Biomol. Chem. 2011, 9, 7327. (d) Li, X.; Incarvito, C. D.; Vogel, T.; Crabtree, R. H. Organometallics 2005, 24, 3066.

  14. Sulikowski, D.; Mąkosza, M. Acta Chim. Slov. 2009, 56, 680.

    CAS  Google Scholar 

  15. Arcadi, A.; Chiarini, M.; Del Vecchio, L.; Marinelli, F.; Michelet, V. Chem. Commun. 2016, 52, 1458.

    Article  CAS  Google Scholar 

  16. Anand, D.; Patel, O. P. S.; Maurya, R. K.; Kant, R.; Yadav, P. P. J. Org. Chem. 2015, 80, 12410.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Lobachevsky State University of Nizhny Novgorod, 23 Gagarin Ave, Nizhny Novgorod, 603950, Russia

    Andrei V. Budruev & Daria Yu. Dzhons

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  1. Andrei V. Budruev
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  2. Daria Yu. Dzhons
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Correspondence to Andrei V. Budruev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(7), 441–443

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Budruev, A.V., Dzhons, D.Y. Synthesis of 2,1-benzisoxazoles (microreview). Chem Heterocycl Comp 52, 441–443 (2016). https://doi.org/10.1007/s10593-016-1908-5

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