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Synthesis and chemical properties of thiochromone and its 3-substituted derivatives (review)

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Chemistry of Heterocyclic Compounds Aims and scope

This review article contains generalized and systematically arranged data about the methods of synthesis and the reactivity of thiochromone and its 3-substituted derivatives published over the previous 40 years.

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References

  1. (a) Schneller, S. W. Adv. Heterocycl. Chem. 1975, 18, 79. (b) Wang, H.-K.; Bastow, K. F.; Cosentino, L. M.; Lee, K.-H. J. Med. Chem. 1996, 39, 1975.

  2. (a) Ellis, G. P. In Comprehensive Heterocyclic Chemistry I; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, Vol. 3, p. 647. (b) Phillips, A. J.; Henderson, J. A.; Jackson, K. L. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier, 2008, Vol. 7, p. 337. (c) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.

  3. (a) Huang, C.-N.; Chuang, R.-R.; Kuo, P.-Y.; Yang, D.-Y. Synlett 2008, 1825. (b) Kumar, P.; Rao, A. T.; Pandey, B. J. Chem. Soc., Chem. Commun. 1992, 1580. (c) Kumar, P.; Bodas, M. S. Tetrahedron 2001, 57, 9755. (d) Vijay, T. A. J.; Nandeesh, K. N.; Raghavendra, G. M.; Rangappa, K. S.; Mantelingu, K. Tetrahedron Lett. 2013, 54, 6533. (e) Lee, J. I.; Kim, M. J. Bull. Korean Chem. Soc. 2011, 32, 1383. (f) Kobayashi, K.; Kobayashi, A.; Ezaki, K. Heterocycles 2012, 85, 1997. (g) Nakazumi, H.; Ueyama, T.; Kitao, T. J. Heterocycl. Chem. 1984, 21, 193.

  4. Razdan, R. K.; Bruni, R. J.; Mehta, A. C.; Weinhardt, K. K.; Papanastassiou, Z. B. J. Med. Chem. 1978, 21, 643.

    Article  CAS  Google Scholar 

  5. Bondock, S.; Metwally, M. A. J. Sulfur Chem. 2008, 29, 623.

    Article  CAS  Google Scholar 

  6. Sosnovskikh, V. Ya. J. Sulfur Chem. 2013, 34, 432.

    Article  CAS  Google Scholar 

  7. (a) Arndt, F.; Flemming, W.; Scholz, E.; Löwensohn, V.; Källner, G.; Eistert, B. Ber. Deutsch. Chem. Ges. 1925, 58, 1612. (b) Krollpfeiffer, F.; Schultze, H.; Schlumbohm, E.; Sommermeyer, E. Ber. Deutsch. Chem. Ges. 1925, 58, 1654.

  8. Still, I. W. J.; Arora, P. C.; Sokolowsky, S. N. Org. Prep. Proced. Int. 1975, 7, 159.

    Article  CAS  Google Scholar 

  9. Cox, P. J.; MacKenzie, N. E.; Thomson, R. H. Tetrahedron Lett. 1981, 22, 2221.

    Article  CAS  Google Scholar 

  10. Holshouser, M. H.; Loeffler, L. J.; Hall, I. H. J. Med. Chem. 1981, 24, 853.

    Article  CAS  Google Scholar 

  11. Giles, P. R.; Marson, C. M. Aust. J. Chem. 1992, 45, 439.

    Article  CAS  Google Scholar 

  12. Nakazumi, H.; Endo, T.; Nakaue, T.; Kitao, T. J. Heterocycl. Chem. 1985, 22, 89.

    Article  CAS  Google Scholar 

  13. (a) Willy, B.; Müller, T. J. J. Synlett 2009, 1255. (b) Willy, B.; Frank, W.; Müller, T. J. J. Org. Biomol. Chem. 2010, 8, 90.

  14. Palani, T.; Park, K.; Song, K. H.; Lee, S. Adv. Synth. Catal. 2013, 355, 1160.

    Article  CAS  Google Scholar 

  15. Dereu, N.; Renson, M.; Mollier, Y.; Le Coustumer, G. J. Organomet. Chem. 1981, 208, 23.

    Article  CAS  Google Scholar 

  16. (a) Iwasaki, H.; Kume, T.; Yamamoto, Y.; Akiba, K. Tetrahedron Lett. 1987, 28, 6355. (b) Ohkata, K.; Ishimaru, K.; Lee, Y.; Akiba, K. Chem. Lett. 1990, 1725. (c) Lee, Y.; Iwasaki, H.; Yamamoto, Y.; Ohkata, K.; Akiba, K. Heterocycles 1989, 29, 35. (d) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058. (e) Langer, P. Synlett 2007, 1016.

  17. Beifuss, U.; Tietze, M.; Gehm, H. Synlett 1996, 182.

  18. Beifuss, U.; Taraschewski, M. J. Chem. Soc., Perkin Trans. 1 1997, 2807.

  19. Beifuss, U.; Schniske, U.; Feder, G. Tetrahedron 2001, 57, 1005.

    Article  CAS  Google Scholar 

  20. (a) Beifuss, U.; Gehm, H.; Noltemeyer, M.; Schmidt, H.-G. Angew. Chem., Int. Ed. 1995, 34, 647. (b) Beifuss, U.; Gehm, H. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 95–96, 339.

  21. Hoettecke, N.; Rotzoll, S.; Albrecht, U.; Lalk, M.; Fischer, C.; Langer, P. Bioorg. Med. Chem. 2008, 16, 10319.

    Article  CAS  Google Scholar 

  22. Liu, J.; Li, Z.; Tong, P.; Xie, Z.; Zhang, Y.; Li, Y. J. Org. Chem. 2015, 80, 1632.

    Article  CAS  Google Scholar 

  23. Hammann, J. M.; Haas, D.; Knochel, P. Angew. Chem., Int. Ed. 2015, 54, 4478.

    Article  CAS  Google Scholar 

  24. Narayan, R.; Antonchick, A. P. Chem. Eur. J. 2014, 20, 4568.

    Article  CAS  Google Scholar 

  25. Chen, C. H.; Reynolds, G. A.; Luss, H. R.; Perlstein, J. H. J. Org. Chem. 1986, 51, 3282.

    Article  CAS  Google Scholar 

  26. Nakazumi, H.; Endo, T.; Sonoda, H.; Kitao, T. J. Heterocycl. Chem. 1985, 22, 821.

    Article  CAS  Google Scholar 

  27. Loutfy, R. O.; Still, I. W. J.; Thompson, M.; Leong, T. S. Can. J. Chem. 1979, 57, 638.

    Article  CAS  Google Scholar 

  28. (a) Ghosh, C. K.; Chakraborty, A. ARKIVOC 2015, (vi), 288. (b) Ibrahim, M. A.; Ali, T. E.-S.; El-Gohary, N. M.; El-Kazak, A. M. Eur. J. Chem. 2013, 4, 311. (c) Plaskon, A. S.; Grygorenko, O. O.; Ryabukhin, S. V. Tetrahedron 2012, 68, 2743. (d) Ghosh, C. K.; Patra, A. J. Heterocycl. Chem. 2008, 45, 1529.

  29. Chen, C. H.; Reynolds, G. A. J. Org. Chem. 1979, 44, 3144.

    Article  CAS  Google Scholar 

  30. (a) Giles, P. R.; Marson, C. M. Tetrahedron Lett. 1990, 31, 5227. (b) Giles, P. R.; Marson, C. M. Tetrahedron 1991, 47, 1303.

  31. Sevenard, D. V.; Vorobyev, M.; Sosnovskikh, V. Ya.; Wessel, H.; Kazakova, O.; Vogel, V.; Shevchenko, N. E.; Nenajdenko, V. G.; Lork, E.; Röschenthaler, G.-V. Tetrahedron 2009, 65, 7538.

    Article  CAS  Google Scholar 

  32. Nakazumi, H.; Torigoe, N.; Kuriyama, T.; Kitao, T. Chem. Express 1986, 1, 21.

    CAS  Google Scholar 

  33. (a) Sigg, I.; Haas, G.; Winkler, T. Helv. Chim. Acta 1982, 65, 275. (b) Rihs, G.; Sigg, I.; Haas, G.; Winkler, T. Helv. Chim. Acta 1985, 68, 1933.

  34. Sosnovskikh, V. Ya.; Sevenard, D. V.; Moshkin, V. S.; Iaroshenko, V. O.; Langer, P. Tetrahedron 2010, 66, 7322.

    Article  CAS  Google Scholar 

  35. Chen, C. H.; Kelts, L. W.; Luss, H. R.; Fox, J. L. J. Org. Chem. 1984, 49, 5143.

    Article  CAS  Google Scholar 

  36. (a) Nakazumi, H.; Maeda, K.; Yagi, S.; Kitao, T. J. Chem. Soc., Chem. Commun. 1992, 1188. (b) Nakazumi, H.; Maeda, K.; Yagi, S.; Kitao, T. J. Mater. Chem. 1999, 9, 2991.

  37. Adams, H.; Bailey, N. A.; Giles, P. R.; Marson, C. M. Acta Cryst. 1991, C47, 1332.

    CAS  Google Scholar 

  38. Sosnovskikh, V. Ya.; Moshkin, V. S. Chem. Heterocycl. Compd. 2012, 48, 139. [Khim. Geterotsikl. Soed. 2012, 144].

  39. (a) Sosnovskikh, V. Ya.; Moshkin, V. S.; El'tsov, O. S. Russ. Chem. Bull., Int. Ed. 2010, 59, 2151. [Izv. Akad. Nauk, Ser. Khim. 2010, 2097.] (b) Sosnovskikh, V. Ya.; Sevenard, D. V.; Moshkin, V. S.; El'tsov, O. S. Russ. Chem. Bull., Int. Ed. 2010, 59, 2155. [Izv. Akad. Nauk, Ser. Khim. 2010, 2101.]

  40. Kikionis, S.; McKee, V.; Markopoulos, J.; Igglessi-Markopoulou, O. Tetrahedron 2008, 64, 5454.

    Article  CAS  Google Scholar 

  41. Cecchetti, V.; Fravolini, A.; Fringuelli, R.; Schiaffella, F.; Lorenzini, M. C.; Tabarrini, O. J. Heterocycl. Chem. 1993, 30, 1143.

    Article  CAS  Google Scholar 

  42. Wentland, M. P.; Lesher, G. Y.; Reuman, M.; Gruett, M. D.; Singh, B.; Aldous, S. C.; Dorff, P. H.; Rake, J. B.; Coughlin, S. A. J. Med. Chem. 1993, 36, 2801.

    Article  CAS  Google Scholar 

  43. (a) Tanaka, M.; Murakami, Y.; Morita, H.; Takagi, K. Chem. Pharm. Bull. 1985, 33, 2129. (b) Takagi, K.; Tanaka, M.; Murakami, Y.; Ogura, K.; Ishii, K.; Morita, H.; Aotsuka, T. J. Heterocycl. Chem. 1987, 24, 1003. (c) Haas, G.; Stanton, J. L.; Winkler, T. J. Heterocycl. Chem. 1981, 18, 619. (d) Iaroshenko, V. O.; Mkrtchyan, S.; Gevorgyan, A.; Vilches-Herrera, M.; Sevenard, D. V.; Villinger, A.; Chochikyan, T. V.; Saghiyan, A.; Sosnovskikh, V. Ya.; Langer, P. Tetrahedron 2012, 68, 2532. (e) Ostrovskyi, D.; Iaroshenko, V. O.; Petrosyan, A.; Dudkin, S.; Ali, I.; Villinger, A.; Tolmachev, A.; Langer, P. Synlett 2010, 2299.

  44. Geissler, J. F.; Roesel, J. L.; Meyer, T.; Trinks, U. P.; Traxler, P.; Lydon, N. B. Cancer Res. 1992, 52, 4492.

    CAS  Google Scholar 

  45. Sevenard, D. V.; Barabanov, M. A.; Sosnovskikh, V. Ya. Russ. Chem. Bull., Int. Ed. 2010, 59, 297. [Izv. Akad. Nauk, Ser. Khim. 2010, 289.]

  46. Barabanov, M. A.; Sevenard, D. V.; Sosnovskikh, V. Ya. Russ. Chem. Bull., Int. Ed. 2012, 61, 2183. [Izv. Akad. Nauk, Ser. Khim. 2012, 2166.]

  47. (a) Sosnovskikh, V. Ya.; Irgashev, R. A. Synlett 2005, 1164. (b) Sosnovskikh, V. Ya.; Irgashev, R. A.; Barabanov, M. A. Synthesis 2006, 2707.

  48. Kotljarov, A.; Sevenard, D. V.; Iaroshenko, V. O.; Irgashev, R. A.; Volochnyuk, D. M.; Langer, P.; Tolmachev, A. A.; Sosnovskikh, V. Ya. Synthesis 2010, 671.

  49. Kotljarov, A.; Irgashev, R. A.; Iaroshenko, V. O.; Sevenard, D. V.; Sosnovskikh, V. Ya. Synthesis 2009, 3233.

  50. Kotljarov, A.; Iaroshenko, V. O.; Volochnyuk, D. M.; Irgashev, R. A.; Sosnovskikh, V. Ya. Synthesis 2009, 3869.

  51. Iaroshenko, V. O.; Bunescu, A.; Sevenard, D. V.; Sosnovskikh, V. Ya.; Langer, P. Russ. Chem. Bull., Int. Ed. 2015, 64, 470. [Izv. Akad. Nauk, Ser. Khim. 2015, 470.]

  52. MacKenzie, N. E.; Thomson, R. H. J. Chem. Soc., Perkin Trans. 1 1982, 395.

  53. Cozzi, P.; Pillan, A. J. Heterocycl. Chem. 1988, 25, 1613.

    Article  CAS  Google Scholar 

  54. Cozzi, P.; Pillan, A. J. Heterocycl. Chem. 1985, 22, 441.

    Article  CAS  Google Scholar 

  55. Nakazumi, H.; Watanabe, S.; Maeda, K.; Kitao, T. Chem. Lett. 1990, 679.

  56. Biswas, K.; Peterkin, T. A. N.; Bryan, M. C.; Arik, L.; Lehto, S. G.; Sun, H.; Hsieh, F.-Y.; Xu, C.; Fremeau, R. T.; Allen, J. R. J. Med. Chem. 2011, 54, 7232.

    Article  CAS  Google Scholar 

  57. Swamy, N. K.; Tatini, L. K.; Babu, J. M.; Annamalai, P.; Pal, M. Chem. Commun. 2007, 1035.

  58. Qi, X.; Xiang, H.; Yang, C. Org. Lett. 2015, 17, 5590.

    Article  CAS  Google Scholar 

  59. Watanabe, S.; Nakazumi, H.; Kitao, T. J. Chem. Soc., Perkin Trans. 1 1988, 1829.

  60. Hofmann, H.; Salbeck, G.; Meyer, B. Chem. Ber. 1970, 103, 2084.

    Article  CAS  Google Scholar 

  61. Katekar, G. F.; Thomson, R. M. Aust. J. Chem. 1972, 25, 647.

    Article  CAS  Google Scholar 

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This study was supported by Program 211 of the Government of the Russian Federation (agreement No. 02.A03.21.0006).

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Correspondence to Vyacheslav Ya. Sosnovskikh.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(7), 427–440

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Sosnovskikh, V.Y. Synthesis and chemical properties of thiochromone and its 3-substituted derivatives (review). Chem Heterocycl Comp 52, 427–440 (2016). https://doi.org/10.1007/s10593-016-1906-7

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