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Synthesis and application of haloisoxazoles

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Chemistry of Heterocyclic Compounds Aims and scope

The review summarizes and analyzes methods for the synthesis of haloisoxazoles, gives examples of their use in modern organic synthesis and medicinal chemistry. The bibliography includes 92 literature sources.

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References

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

    Article  CAS  Google Scholar 

  2. (a) Sysak, A.; Obmińska-Mrukowicz, B. Eur. J. Med. Chem. 2017, 137, 292. (b) Pairas, G. N.; Perperopoulou, F.; Tsoungas, P. G.; Varvounis, G. ChemMedChem 2017, 12, 408. (c) Zhu, J.; Mo, J.; Lin, H.-Z.; Chen, Y.; Sun, H.-P. Bioorg. Med. Chem. 2018, 26, 3065. (d) Bondarenko, O. B.; Zyk, N. V. Chem. Heterocycl. Compd. 2020, 56, 694. [Khim. Geterotsikl. Soedin. 2020, 56, 694.]

  3. (a) Hu, F.; Szostak, M. Adv. Synth. Catal. 2015, 357, 2583. (b) Morita, T.; Yugandar, S.; Fuse, S.; Nakamura, H. Tetrahedron Lett. 2018, 59, 1159.

  4. Metal-Catalyzed Cross-Coupling Reactions II; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.

  5. (a) Waldo, J. P.; Mehta, S.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2008, 10, 658. (b) Takenaka, K.; Nakatsuka, S.; Tsujihara, T.; Koranne, P. S.; Sasai, H. Tetrahedron: Asymmetry 2008, 19, 2492.

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

  7. (a) Vinick, F. J.; Pan, Y.; Gschwend, H. W. Tetrahedron Lett. 1978, 19, 4221. (b) Schöllkopt, U.; Hoppe, I. Angew. Chem., Int. Ed. 1975, 14, 765. (c) Hoppe, I.; Schöllkopf, U. Liebigs Ann. Chem. 1979, 219.

  8. (a) Fusco, R.; Rossi, S. Chem. Ind. 1957, 1650. (b) Carr, J. B.; Durham, H. G.; Hass, D. K. J. Med. Chem. 1977, 20, 934.

  9. Nesmeyanov, A. N.; Rybin, L. V.; Rybinskaya, M. I.; Sokolov, S. D. Chem. Heterocycl. Compd. 1967, 3, 633. [Khim. Geterotsikl. Soedin. 1967, 800.]

  10. Schlewer, G.; Krogsgaard-Larsen, P. Acta Chem. Scand., Ser. B: Org. Chem. Biochem. 1984, 38B, 815.

  11. (a) Chiarino, D.; Napoletano, M.; Sala, A. J. Heterocycl. Chem. 1987, 24, 43. (b) Grob, J. E.; Nunez, J.; Dechantsreiter, M. A.; Hamann, L. G. J. Org. Chem. 2011, 76, 10241.

  12. Halling, K.; Thomsen, I.; Torssell, K. B. G. Liebigs Ann. Chem. 1989, 985.

  13. Kovalenko, S. V.; Gorin, V. I.; Martynov, I. V. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1989, 38, 1335. [Izv. Akad. Nauk, USSR, Ser. Khim.1989, 1454.]

  14. Bravo, P.; Gaudiano, G.; Quilico, A.; Ricca, A. Gatz. Chim. Ital. 1961, 91, 47.

    CAS  Google Scholar 

  15. Dighe, S. U.; Mukhopadhyay, S.; Kolle, S.; Kanojiya, S.; Batra, S. Angew. Chem., Int. Ed. 2015, 54, 10926.

    Article  CAS  Google Scholar 

  16. Moore, J. E.; Davies, M. W.; Goodenough, K. M.; Wybrow, R. A. J.; York, M.; Johnson, C. N.; Harrity, J. P. A. Tetrahedron 2005, 61, 6707.

    Article  CAS  Google Scholar 

  17. Chen, W.; Zhang, J.; Wang, B.; Zhao, Z.; Wang, X.; Hu, Y. J. Org. Chem. 2015, 80, 2413.

    Article  CAS  Google Scholar 

  18. Quilico, A.; Justoni, R. Rend. Ist. Lombardo Sci. 1936, 69, 587; Chem. Abstr. 1938, 32, 7455.

  19. Rostovskii, N. V.; Agafonova, A. V.; Smetanin, I. A.; Novikov, M. S.; Khlebnikov, A. F.; Ruvinskaya, J. O.; Starova, G. L. Synthesis 2017, 4478.

  20. Sokolov, S. D.; Kochetkov, N. K. Dokl. Akad. Nauk USSR 1964, 156, 1391.

    CAS  Google Scholar 

  21. Sokolov, S. D.; Yudinceva, I. M. Zh. Org. Khim. 1971, 7, 1765.

    CAS  Google Scholar 

  22. (a) Kochetkov, N. K.; Sokolov, S. D.; Vagurtova, N. M. Zh. Obshch. Khim. 1961, 31, 2326. (b) Bondarenko, O. B.; Komarov, A. I.; Karetnikov, G. L. RF Patent 2711558; Inventions Utility Models. Official Bulletin of the Federal Service for Intellectual Property (Rospatent) 2020, (20).

  23. (a) Frølund, B.; Jørgensen, A. T.; Tagmose, L.; Stensbøl, T. B.; Vestergaard, H. T.; Engblom, C.; Kristiansen, U.; Sanchez, C.; Krogsgaard-Larsen, P.; Liljefors, T. J. Med. Chem. 2002, 45, 2454. (b) Kromann, H.; Sløk, F. A.; Johansen, T. N.; Krogsgaard-Larsen, P. Tetrahedron 2001, 57, 2195.

  24. (a) Micetich, R. G.; Chin, C. G. Can. J. Chem. 1970, 48, 1371. (b) Choi, M. J.; No, E. S.; Thorat, D. A.; Jang, J. W.;Yang, H.; Lee, J.; Choo, H.; Kim, S. J.; Lee, C. S.; Ko, S. Y.; Lee, J.; Nam, G.; Pae, A. N. J. Med. Chem. 2013, 56, 9008.

  25. Day, R. A.; Blake, J. A.; Stephens, C. E. Synthesis 2003, 1586.

  26. Chrisope, D. R.; Keel, R. A.; Baumstark, A. L.; Boykin, D. W. J. Heterocycl. Chem. 1981, 18, 795.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  28. (a) Palin, R.; Abernethy, L.; Ansari, N.; Cameron, K.; Clarkson, T.; Dempster, M.; Dunn, D.; Easson, A.-M.; Edwards, D.; Maclean, J.; Everett, K.; Feilden, H.; Ho, K.-K.; Kultgen, S.; Littlewood, P.; McArthur, D.; McGregor, D.; McLuskey, H.; Neagu, I.; Neale, S.; Nisbet, L.-A.; Ohlmeyer, M.; Pham, Q.; Ratcliffe, P.; Rong, Y.; Roughton, A.; Sammons, M.; Swanson, R.; Tracey, H.; Walker, G. Bioorg. Med. Chem. Lett. 2011, 21, 892. (b) Ratcliffe, P.; Abernethy, L.; Ansari, N.; Cameron, K.; Clarkson, T.; Dempster, M.; Dunn, D.; Easson, A.-M.; Edwаrds, D.; Everett, K.; Feilden, H.; Ho, K.-K.; Kultgen, S.; Littlewood, P.; Maclean, J.; McArthur, D.; McGregor, D.; McLuskey, H.; Neagu, I.; Nimz, O.; Nisbet, L.-A.; Ohlmeyer, M.; Palin, R.; Pham, Q.; Rong, Y.; Roughton, A.; Sammons, M.; Swanson, R.; Tracey, H.; Walker, G. Bioorg. Med. Chem. Lett. 2011, 21, 4652.

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

    Article  CAS  Google Scholar 

  30. Wang, X.-C.; Hu, Y.; Bonacorsi, S.; Hong, Y.; Burrell, R.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 10326.

    Article  CAS  Google Scholar 

  31. (a) Bumgardner, C. L.; Sloop, J. C. J. Fluorine Chem. 1992, 56, 141. (b) Sloop, J. C.; Bumgardner, C. L.; Loehle, W. D. J. Fluorine Chem. 2002, 118, 135.

  32. Stephens, C. E.; Blake, J. A. J. Fluorine Chem. 2004, 125, 1939.

    Article  CAS  Google Scholar 

  33. Khisamutdinov, G. Kh.; Okhlobystina, L. V.; Fainzil'berg, A. A. Russ. Chem. Bull., Int. Ed. 2009, 58, 2182. [Izv. Akad. Nauk, Ser. Khim. 2009, 2117.]

  34. Bondarenko, O. B.; Komarov, A. I.; Karetnikov, G. L.; Nikolaeva, S. N.; Zyk, N. V.; Holt, T.; Kutateladze, A. G. Tetrahedron 2019, 75, 130666.

    Article  Google Scholar 

  35. Sato, K.; Sandford, G.; Shimizu, K.; Akiyama, S.; Lancashire, M. J.; Yufit, D. S.; Tarui, A.; Omote, M.; Kumadaki, I.; Harusawa, S.; Ando, A. Tetrahedron Lett. 2016, 72, 1690.

    Article  CAS  Google Scholar 

  36. Jeong, Y.; Kim, B.-I.; Lee, J. K.; Ryu, J.-S. J. Org. Chem. 2014, 79, 6444.

    Article  CAS  Google Scholar 

  37. Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 7, 5203.

    Article  CAS  Google Scholar 

  38. Debleds, O.; Gayon, E.; Ostaszuk, E.; Vrancken, E.; Campagne, J.-M. Chem.–Eur. J. 2010, 16, 12207.

    Article  CAS  Google Scholar 

  39. Kaewsri, W.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. RSC Adv. 2016, 6, 48666.

    Article  CAS  Google Scholar 

  40. Okitsu, T.; Sato, K.; Potewar, T. M.; Wada, A. J. Org. Chem. 2011, 76, 3438.

    Article  CAS  Google Scholar 

  41. Jackowski, O.; Lecourt, T.; Micouin, L. Org. Lett. 2011, 13, 5664.

    Article  CAS  Google Scholar 

  42. Crossley, J. A.; Browne, D. L. J. Org. Chem. 2010, 75, 5414.

    Article  CAS  Google Scholar 

  43. (a) McIntosh, M. L.; Naffziger, M. R.; Ashburn, B. O.; Zakharov, L. N.; Carter, R. G. Org. Biomol. Chem. 2012, 10, 9204. (b) Oakdale, J. S.; Sit, R. K.; Fokin, V. V. Chem.–Eur. J. 2014, 20, 11101.

  44. Danheiser, R. L.; Becker, D. A. Heterocycles 1987, 25, 277.

    Article  CAS  Google Scholar 

  45. (a) Griesbeck, A. G.; Franke, M.; Neudörfl, J.; Kotaka, H. Beilstein J. Org. Chem. 2011, 7, 127. (b) Adembri, G.; Tedeschi, P. Boll. Sci. Fac. Chim. Ind. Bologna 1965, 23, 203. (c) Rajender, P. S.; Sridevi, G.; Reddy, K. K. Synth. Commun. 2012, 42, 2191. (d) Alyabyev, S. B.; Kravchenko, D. V.; Dorogov, M. V.; Ivachtchenko, А. V. Khim. Khim. Tekhnol. 2007, 50, 47. (e) Gibbons, L. K. US Patent 3781438.

  46. Saito, N.; Kurihara, T.; Yasuda, S.; Akagi, M. Yakugaku Zasshi 1970, 90, 32.

    Article  CAS  Google Scholar 

  47. Chi, K.-W.; Kim, H.-A.; Furin, G. G.; Zhuzhgov, E. L.; Protzuk, N. J. Fluorine Chem. 2001, 110, 11.

    Article  CAS  Google Scholar 

  48. Miller, S. I.; Tanaka, R. J. Org. Chem. 1971, 36, 3856.

    Article  CAS  Google Scholar 

  49. Schäfer, E.; Christiansen, J. J. J. Mol. Struct. 1983, 97, 101.

    Article  Google Scholar 

  50. Ku, Y.-Y.; Grieme, T.; Sharma, P.; Pu, Y.-M.; Raje, P.; Morton, H.; King, S. Org. Lett. 2001, 3, 4185.

    Article  CAS  Google Scholar 

  51. (a) Kondo, Y.; Uchiyama, D.; Sakamoto, T.; Yamanaka, H. Tetrahedron Lett. 1989, 30, 4249. (b) Sakamoto, T.; Kondo, Y.; Uchiyama, D.; Yamanaka, H. Tetrahedron 1991, 47, 5111.

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

    Article  CAS  Google Scholar 

  53. (a) Stevens, R. V.; Albizati, K. F. Tetrahedron Lett. 1984, 25, 4587. (b) Lakhvich, F. A.; Koroleva, E. V. Chem. Heterocycl. Compd. 1994, 30, 375. [Khim. Geterotsikl. Soedin. 1994, 424.]

  54. Sagingova, L. G.; Alhamdan, M.; Petrosyan, V. S. Vestn. Mosk. Univ., Ser. Khim. 2 1998, 39, 339.

    Google Scholar 

  55. Lin, S.-T.; Lin, L.-H.; Yao, Y.-F. Tetrahedron Lett. 1992, 33, 3155.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  57. (a) Bondarenko, O. B.; Vinogradov, A. A.; Komarov, А. I.; Karetnikov, G. L.; Zyk, N. V.; Holt, T.; Kutateladze, A. G. Tetrahedron 2019, 75, 2861. (b) Bondarenko, O. B.; Vinogradov, A. A.; Danilov, P. А.; Nikolaeva, S. N.; Gavrilova, A. Yu.; Zyk, N. V. Tetrahedron Lett. 2015, 56, 6577. (c) Bondarenko, O. B.; Vinogradov, A. A.; Komarov, A. I.; Smirnov, A. S.; Zyk, N. V. J. Fluorine Chem. 2016, 185, 201.

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

  59. Bondarenko, O. B.; Gavrilova, A. Yu.; Murodov, D. S.; Zlotskii, S. S.; Zyk, N. V.; Zefirov, N. S. Tetrahedron Lett. 2013, 54, 1845.

    Article  CAS  Google Scholar 

  60. Bondarenko, O. B.; Gavrilova, A. Yu.; Murodov, D. S.; Zyk, N. V.; Zefirov, N. S. Mendeleev Commun. 2011, 21, 188.

    Article  CAS  Google Scholar 

  61. Bondarenko, O. B.; Garaev, Z. M.; Komarov, A. I.; Kuznetsova, L. I.; Gutorova, S. V.; Skvortsov, D. A.; Zyk, N. V. Mendeleev Commun. 2019, 29, 419.

    Article  CAS  Google Scholar 

  62. Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  64. Li, F.; Hu, Y.; Wang, Y.; Ma, C.; Wang, J. J. Med. Chem. 2017, 60, 1580.

    Article  CAS  Google Scholar 

  65. (a) Anderson, D. J.; Muchmore, C. R. J. Heterocycl. Chem. 1995, 32, 1189. (b) Fernandes, A. A. G.; da Silva, A. F.; Okada, C. Y., Jr.; Suzukawa, V.; Cormanich, R. A.; Jurberg, I. D. Eur. J. Org. Chem. 2019, 3022.

  66. Nantermet, P. G.; Barrow, J. C.; Lundell, G. F.; Pellicore, J. M.; Rittle, K. E.; Young, M. B.; Freidinger, R. M.; Connolly, T. M.; Condra, C.; Karczewski, J.; Bednar, R. A.; Gaul, S. L.; Gould, R. J.; Prendergast, K.; Selnick, H. G. Bioorg. Med. Chem. Lett. 2002, 12, 319.

    Article  CAS  Google Scholar 

  67. Ponticelli, F.; Tedeschi, P. Synthesis 1985, 792.

  68. Agafonova, A. V.; Smetanin, I. A.; Rostovskii, N. V.; Khlebnikov, A. F.; Novikov, M. S. Chem. Heterocycl. Compd. 2017, 53, 1068. [Khim. Geterotsikl. Soedin. 2017, 53, 1068.]

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  1. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Oksana B. Bondarenko & Nikolai V. Zyk

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(12), 1523–1534

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Bondarenko, O.B., Zyk, N.V. Synthesis and application of haloisoxazoles. Chem Heterocycl Comp 56, 1523–1534 (2020). https://doi.org/10.1007/s10593-020-02845-8

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