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Synthesis of fused pyrazoles via intramolecular cyclization of appropriately ortho-substituted nitroarenes and nitroheteroarenes

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Chemistry of Heterocyclic Compounds Aims and scope

Among numerous approaches for the synthesis of condensed heterocycles bearing a pyrazole nucleus, the intramolecular cyclization of a suitable ortho-substituted nitroaromatic and nitroheteroaromatic precursors is one of the most convenient routes. This review summarizes recent developments in the application of this approach for the synthesis of fused pyrazoles, their 1-oxides, and 1-hydroxy derivatives.

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References

  1. Cerecetto, H.; Gerpe, A.; González, M.; Arán, V. J.; de Ocáriz, C. O. Mini Rev. Med. Chem. 2005, 5, 869.

    Article  CAS  Google Scholar 

  2. Schmidt, A.; Beutler, A.; Snovydovych, B. Eur. J. Org. Chem. 2008, 4073.

  3. Thangadurai, A.; Minu, M.; Wakode, S.; Agrawal, S.; Narasimhan, B. Med. Chem. Res. 2012, 21, 1509.

    Article  CAS  Google Scholar 

  4. Kumar, V.; Kaur, K.; Gupta, G. K.; Sharma, A. K. Eur. J. Med. Chem. 2013, 69, 735.

    Article  CAS  Google Scholar 

  5. Meng, L.; Zhao, B.-X. Eur. J. Med. Chem. 2014, 85, 311.

    Article  Google Scholar 

  6. Raffa, D.; Maggio, B.; Raimondi, M. V.; Cascioferro, S.; Plescia, F.; Cancemi, G; Daidone, G. Eur. J. Med. Chem. 2015, 97, 732.

    Article  CAS  Google Scholar 

  7. Balfour, J. A.; Clissold, S. P. Drugs 1990, 39, 575.

    Article  CAS  Google Scholar 

  8. Sanger, G. J.; Nelson, D. R. Eur. J. Pharm. 1989, 159, 113.

    Article  CAS  Google Scholar 

  9. Hesketh, P. J.; Gandara, D. R. J. Nat. Cancer Inst. 1991, 83, 613.

    Article  CAS  Google Scholar 

  10. Dudak, S. D.; Lopez, A.; Block, N. L.; Lokeshwar, B. L. Anticancer Res. 1996, 16, 3665.

    CAS  Google Scholar 

  11. Forster, R.; Campana, A.; D'Onofrio, E.; Henderson, L.; Mosesso, P.; Sforza Barcellona, P. Carcinogenesis 1990, 11, 1509.

    Article  CAS  Google Scholar 

  12. Rugo, H. S.; Herbst, R. S.; Liu, G.; Park, J. W.; Kies, M. S.; Steinfeldt, H. M.; Pithavala, Y. K.; Reich, S. D.; Freddo, J. L.; Wilding, G. J. Clin. Oncol. 2005, 23, 5474.

    Article  CAS  Google Scholar 

  13. Atta-ur-Rahman; Malik, S.; He, C.; Clardy, J. Tetrahedron Lett. 1985, 26, 2759.

    Article  CAS  Google Scholar 

  14. Atta-ur-Rahman; Malik, S.; Hasan, S. S.; Choudhary, M. I.; Ni, C.-Z.; Clardy, J. Tetrahedron Lett. 1995, 36, 1993.

    Article  CAS  Google Scholar 

  15. Liu, Y.-M.; Yang, J.-S.; Liu, Q.-H. Chem. Pharm. Bull. 2004, 52, 454.

    Article  CAS  Google Scholar 

  16. Liu, Y.-M.; Jiang, Y.-H.; Liu, Q.-H.; Chen, B.-Q. Phytochem. Lett. 2013, 6, 556.

    Article  CAS  Google Scholar 

  17. (a) Steeghs, N.; Eskens, F. A. L. M.; Gelderblom, H.; Verweij, J; Nortier, J. W. R.; Ouwerkerk, J.; Van Noort, C.; Mariani, M.; Spinelli, R.; Carpinelli, P.; Laffranchi, B. J. Clin. Oncol. 2009, 27, 5094. (b) https://clinicaltrials.gov/ct2/show/NCT00766324.

  18. Gresser, U.; Gleiter, C. H. Eur. J. Med. Res. 2002, 7, 435.

    CAS  Google Scholar 

  19. Buchanan, J. G., Edgar, A. R.; Hutchison, R. J.; Stobie, A.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1980, 237.

  20. Smirnov, V. V.; Kiprianova, E. A.; Garagulya, A. D.; Esipov, S. E.; Dovjenko, S. A. FEMS Microbiol. Lett. 1997, 153, 357.

    Article  CAS  Google Scholar 

  21. Stadlbauer, W. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Neier, R, Ed.; Georg Thieme Verlag: Stuttgart, 2002, 5th ed., Vol. 12, p. 227.

  22. (a) The Chemistry of the Nitro and Nitroso Groups; Feuer, H., Ed.; Interscience: New York, 1969, Vol. 1. (b) The Chemistry of the Nitro and Nitroso Groups; Feuer, H., Ed.; Interscience: New York, 1970, Vol. 2.

  23. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.

    Book  Google Scholar 

  24. Yan, G.; Yang, M. Org. Biomol. Chem. 2013, 11, 2554.

    Article  CAS  Google Scholar 

  25. Topics in Heterocyclic Chemistry; Charushin, V.; Chupakhin, O., Eds.: Springer: Heidelberg, 2014, Vol. 37.

  26. Terrier, F. Modern Nucleophilic Aromatic Substitution; Wiley-VCH: Weinheim, 2013.

    Book  Google Scholar 

  27. Mąkosza, M. Chem. Soc. Rev. 2010, 39, 2855.

    Article  Google Scholar 

  28. Loudon, J. D.; Tennant, G. Quart. Rev., Chem. Soc. 1964, 389.

  29. Preston, P. N.; Tennant, G. Chem. Rev. 1972, 72, 627.

    Article  CAS  Google Scholar 

  30. Ballini, R.; Araújo, N.; Gil, M. V.; Román, E.; Serrano, J. A. Chem. Rev. 2013, 113, 3493.

    Article  CAS  Google Scholar 

  31. Heller, G.; Spielmeyer, G. Ber. Dtsch. Chem. Ges. 1925, 58, 834.

    Article  Google Scholar 

  32. Gerpe, A.; Aguirre, G.; Boiani, L.; Cerecetto, H.; González, M.; Olea-Azar, C.; Rigol, C.; Maya, J. D.; Morello, A.; Piro, O. E.; Arán, V. J.: Azqueta, A.; López de Ceráin, A.; Monge, A.; Rojas, M. A.; Yaluff, G. Bioorg. Med. Chem. 2006, 14, 3467.

    Article  CAS  Google Scholar 

  33. Nyerges, M.; Fejes, I.; Virányi, A.; Groundwater, P. W.; Tőke, L. Tetrahedron Lett. 2001, 42, 5081.

    Article  CAS  Google Scholar 

  34. Nyerges, M.; Virányi, A.; Zhang, W.; Groundwater, P. W.; Blaskó, G.; Tőke, L. Tetrahedron 2004, 60, 9937.

    Article  CAS  Google Scholar 

  35. Nyerges, M.; Somfai, B.; Tóth, J.; Tőke, L.; Dancsó, A.; Blaskó, G. Synthesis 2005, 2039.

  36. Groundwater, P. W.; Nyerges, M. Adv. Heterocycl. Chem. 1999, 73, 97;

    Article  CAS  Google Scholar 

  37. Nyerges, M.; Virányi, A.; Tóth, J.; Blaskó, G.; Tőke, L. Synthesis 2006, 1273.

  38. Arany, A.; Bendell, D.; Groundwater, P. W.; Garnett, I.; Nyerges, M. J. Chem. Soc., Perkin Trans. 1 1999, 2605.

  39. Bouillon, I.; Zajíček, J.; Pudelová, N.; Krchňák, V. J. Org. Chem. 2008, 73, 9027.

    Article  CAS  Google Scholar 

  40. Senda, S.; Hirota, K.; Asao, T.; Yamada, Y. J. Chem. Soc., Chem. Commun. 1977, 556.

  41. Hirota, K.; Yamada, Y.; Asao, T.; Senda, S. J. Chem. Soc., Perkin I 1982, 277.

  42. Nicolaou, K. C.; Lee, S. H.; Estrada, A. A.; Zak, M. Angew. Chem. 2005, 117, 3802.

    Article  Google Scholar 

  43. Nicolaou, K. C.; Estrada, A. A.; Lee, S. H.; Freestone, G. C. Angew. Chem. 2006, 118, 5490.

    Article  Google Scholar 

  44. Steglich, W.; Kübel, B.; Gruber, P. Chem. Ber. 1973, 106, 2870.

    Article  CAS  Google Scholar 

  45. D'Anello, M.; Erba, E.; Gelmi, M. L.; Pocar, D. Chem. Ber. 1988, 121, 67.

    Article  Google Scholar 

  46. Slevin, Å.; Koolmeister, T.; Scobie, M. Chem. Commun. 2007, 2506.

  47. Lehmann, F.; Koolmeister, T.; Odell, L. R.; Scobie, M. Org. Lett. 2009, 11, 5078.

    Article  CAS  Google Scholar 

  48. Kurth, M. J.; Olmstead, M. M.; Haddadin, M. J. J. Org. Chem. 2005, 70, 1060.

    Article  CAS  Google Scholar 

  49. Mills, A. D.; Nazer, M. Z.; Haddadin, M. J.; Kurth, M. J. J. Org. Chem. 2006, 71, 2687.

    Article  CAS  Google Scholar 

  50. Mills, A. D.; Maloney, P.; Hassanein, E.; Haddadin, M. J.; Kurth, M. J. J. Comb. Chem. 2007, 9, 171.

    Article  CAS  Google Scholar 

  51. Butler, J. D.; Solano, D. M.; Robins, L. I.; Haddadin, M. J.; Kurth, M. J. J. Org. Chem. 2008, 73, 234.

    Article  CAS  Google Scholar 

  52. Solano, D. M.; Butler, J. D.; Haddadin, M. J.; Kurth, M. J. Org. Synth. 2010, 87, 339.

    Article  CAS  Google Scholar 

  53. Avila, B.; El-Dakdouki, M. H.; Nazer, M. Z.; Harrison, J. G.; Tantillo, D. J.; Haddadin, M. J.; Kurth, M. J. Tetrahedron Lett. 2012, 53, 6475.

    Article  CAS  Google Scholar 

  54. Oakdale, J. S.; Solano, D. M.; Fettinger, J. C.; Haddadin, M. J.; Kurth, M. J. Org. Lett. 2009, 11, 2760.

    Article  CAS  Google Scholar 

  55. Donald, M. B.; Conrad, W. E.; Oakdale, J. S.; Butler, J. D.; Haddadin, M. J.; Kurth, M. J. Org. Lett. 2010, 12, 2524.

    Article  CAS  Google Scholar 

  56. Farber, K. M.; Haddadin, M. J.; Kurth, M. J. J. Org. Chem. 2014, 79, 6939.

    Article  CAS  Google Scholar 

  57. Avila, B.; Solano, D. M.; Haddadin, M. J.; Kurth, M. J. Org. Lett. 2011, 13, 1060.

    Article  CAS  Google Scholar 

  58. Hurst, J.; Wibberley, D. G. J. Chem. Soc. (C) 1968, 1487.

  59. Cadogan, J. I. G. Quart Rev., Chem. Soc. 1962, 208.

  60. Cadogan, J. I. G.; Mackie, G. Org. Syn. Coll. 1973, 5, 941.

    Google Scholar 

  61. Varughese, D. J.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 2006, 47, 6795.

    Article  CAS  Google Scholar 

  62. Armour, M.-A.; Cadogan, J. I. G.; Grace, D. S. B. J. Chem. Soc., Perkin Trans. 2 1975, 1185.

  63. Genung, N. E.; Wei, L.; Aspnes, G. E. Org. Lett. 2014, 16, 3114.

    Article  CAS  Google Scholar 

  64. Stanforth, S. P. J. Heterocycl. Chem. 1987, 24, 531.

    Article  CAS  Google Scholar 

  65. Balog, J.; Riedl, Z.; Hajós, G. Tetrahedron Lett. 2013, 54, 5338.

    Article  CAS  Google Scholar 

  66. Akazome, M.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1994, 59, 3375.

    Article  CAS  Google Scholar 

  67. Okuro, K.; Gurnham, J.; Alper, H. Tetrahedron Lett. 2012, 53, 620.

    Article  CAS  Google Scholar 

  68. Sawant, D.: Kumar, R.; Maulik, P. R.; Kundu, B. Org. Lett. 2006, 8, 1525.

    Article  CAS  Google Scholar 

  69. Shi, D. Q.; Dou, G.-L.; Ni, S.-N.; Shi, J.-W.; Li, X.-Y.; Wang, X.-S.; Wu, H.; Ji, S.-J. Synlett 2007, 2509.

  70. McMurry, J. E. Acc. Chem. Res. 1974, 7, 281.

    Article  CAS  Google Scholar 

  71. McMurry, J. E. Chem. Rev. 1989, 89, 1513.

    Article  CAS  Google Scholar 

  72. Lin, W.; Hu, M.; Feng, X.; Cao, C.; Huang, Z.; Shi, D. J. Heterocycl. Chem. 2015, 52, 1170.

    Article  CAS  Google Scholar 

  73. Sun, F.; Feng, X.; Zhao, X.; Huang, Z.-B.; Shi, D. Tetrahedron 2012, 68, 3851.

    Article  CAS  Google Scholar 

  74. Dou, G.; Shi, D. J. Comb. Chem. 2009, 11, 1073.

    Article  CAS  Google Scholar 

  75. Pitts, M. R.; Harrison, J. R.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 2001, 955.

  76. Augé, J.; Lubin-Germain, N.; Uziel, J. Synthesis 2007, 1739.

  77. Bernardi, L.; Bonini, B. F.; Capitò, E.; Dessole, G.; Comes-Franchini, M.; Fochi, M.; Ricci, A. J. Org. Chem. 2004, 69, 8168.

    Article  CAS  Google Scholar 

  78. Cicchi, S.; Bonanni, M.; Cardona, F.; Revuelta, J.; Goti, A. Org. Lett. 2003, 5, 1773.

    Article  CAS  Google Scholar 

  79. Han, R.; Son, K. I.; Ahn, G. H.; Jun, Y. M.; Lee, B. M.; Park, Y.; Kim, B. H. Tetrahedron Lett. 2006, 47, 7295.

    Article  CAS  Google Scholar 

  80. Ahn, G. H.; Lee, J. J.; Jun, Y. M.; Lee, B. M.; Kim, B. H. Org. Biomol. Chem. 2007, 5, 2472.

    Article  CAS  Google Scholar 

  81. Kim, B. H.; Jin, Y.; Jun, Y. M.; Han, R.; Baik, W.; Lee, B. M. Tetrahedron Lett. 2000, 41, 2137.

    Article  CAS  Google Scholar 

  82. Kim, B. H.; Lee, Y. S.; Kwon, W.; Jin, Y.; Tak, J. A.; Jun, Y. M.; Baik, W.; Lee, B. M. Heterocycles 1998, 48, 2581.

    Article  CAS  Google Scholar 

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    Grigoriy Ya. Remennikov

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(2), 101–115

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Remennikov, G.Y. Synthesis of fused pyrazoles via intramolecular cyclization of appropriately ortho-substituted nitroarenes and nitroheteroarenes. Chem Heterocycl Comp 53, 101–115 (2017). https://doi.org/10.1007/s10593-017-2028-6

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