Skip to main content
SpringerLink
Log in

2,1-Bensoidoxazoles [anthranils]. Synthesis and opening of the isoxazole ring (review)

  • Methods of Synthesis and Technology of Drug Production
  • Published:
Pharmaceutical Chemistry Journal Aims and scope

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Literature cited

  1. S. A. Andronati, A. A. Mazurov, and A. S. Yavorskii, Ukr. Khim. Zh.,46, No. 8, 823–826 (1980).

    Google Scholar 

  2. V. G. Granik, V. M. Pechenina, N. A. Mukhina, et al., Khim.-farm. Zh., No. 6, 692–695 (1989).

    Google Scholar 

  3. S. S. Mochalov, T. P. Surikova, and Yu. S. Shabrov, Khim. Geterotsikl. Soedin., No. 7, 886–889 (1976).

    Google Scholar 

  4. S. S. Mochalov, A. N. Fedotov, and Yu. S. Shabarov, Zh. Org. Khim.,16, No. 2, 462–466 (1980).

    Google Scholar 

  5. N. A. Mukhina, V. M. Pechenina, V. G. Klimenko, and N. P. Suvorova, Author's Cert. (USSR) No. 857,944; Otkrytiya, No. 26 (1982).

  6. N. A. Mukhina, V. M. Pechenina, V. G. Klimenko, and V. G. Granik, Author's Cert. (USSR) No. 1,049,487; ibid., No. 39 (1983).

  7. V. M. Pechenina, N. A. Mukhina, V. G. Klimenko, and V. G. Granik, Advances in the Technology of Production of Pharmaceutical Chemicals, and the Identification and Development of New Medicinals [in Russian], Novokuznetsk (1986), pp. 174–175.

  8. V. M. Pechenina, N. A. Mukhina, V. G. Klimenko, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 6, 857 (1986).

    Google Scholar 

  9. V. M. Pechenina, V. G. Klimenko, and V. G. Granik, ibid., No. 8, 1082–1085.

    Google Scholar 

  10. A. S. Favorskii and A. A. Mazurov, Khim. Prom-st'. Ser. Reagenty Osobo Chist. vesh., No. 6, 53 (1980).

    Google Scholar 

  11. Brit. Pat. No. 1,460,141 (1970); Chem. Abstr.,87, P22781d (1977).

  12. East German Pat. No. 61,625 (1968); ibid.,70, P37806p (1969).

  13. East German Pat. No. 158,241 (1983); ibid.,99, P53736v (1984).

  14. East German Pat. No. 219,192 (1985); ibid.,103, P178255h (1985).

  15. Indian Pat. No. 139213 (1976); ibid.,92, P14643u (1980).

  16. Indian Pat. No. 148644 (1981); ibid.,96, P162756k (1982).

  17. Polish Pat. No. 119683 (1983); ibid.,100, P338760m (1984).

  18. Rumanian Pat. No. 54775 (1973); ibid.,80, P59695k (1974).

  19. Rumanian Pat. No. 82486 (1983); ibid.,101, P1303907z (1985).

  20. Rumanian Pat. No. 43507 (1966); Ref. Zh. Khim., No. 17, 17N152 (1967).

  21. US Patent No. 3609145 (1971); Chem. Abstr.,75, P140899y (1971).

  22. US Pat. No. 3642897 (1972); ibid.,76, P153341f (1972).

  23. US Pat. No. 3900501 (1975); ibid.,84, P44187e (1976).

  24. West German Pat. No. 2163522 (1972); ibid.,77, P126705s (1972).

  25. West German Pat. No. 2163642 (1972); ibid., P140181z.

  26. West German Pat. No. 2400689 (1975); ibid.,84, P43633k (1976).

  27. West German Pat. No. 2529292 (1976); ibid., P135627g.

  28. Czech Pat. No. 164184 (1976); ibid.,86, P106178e (1977).

  29. Czech Pat. No. 224,238 (1982); ibid.,102, P45623w (1985).

  30. Jap. Pat. No. 44-26663 (1969); ibid.,72, P12708m (1970).

  31. Jap. Pat. No. 49-39997 (1974); ibid.,82, P139695s (1975).

  32. Jap. Pat. No. 49-41196 (1974); ibid.,82, P170384p (1965).

  33. Jap. Pat. No. 52-51350 (1977); ibid.,88, P37423h (1978).

  34. Jap. Pat. No. 52-83429 (1977); ibid., P6568e.

  35. Jap. Pat. No. 60-252472 (1985); ibid.,104, P207253w (1986).

  36. R. M. Acheson, R. G. Boulton, and J. Hunter, J. Chem., Soc., C., No. 8, 1067–1071 (1970).

    Google Scholar 

  37. V. Askam and R. H. Z. Deck, ibid., No. 10, 1243–1246 (1968).

    Google Scholar 

  38. S. N. Balasubrahmanyanyam and A. S. Radhakrishna, J. Org. Chem.,42, No. 5, 897–902 (1977).

    Google Scholar 

  39. M. A. Berwick, J. Amer. Chem. Soc.,93, No. 22, 1087–5786 (1971).

    Google Scholar 

  40. R. S. Boruah, J. S. Sandhu, and G. Thyagarajan, J. Het. Chem.,16, No. 5, 1087–1091 (1979).

    Google Scholar 

  41. R. S. Boruah, J. S. Sandhu, and G. Thyagarajan, ibid.,18, No. 6, 1081–1085 (1981).

    Google Scholar 

  42. A. J. Boulton, J. J. Fletcher, and A. R. Katritsky, Chem. Commun., No. 1, 62–66 (1968).

    Google Scholar 

  43. A. J. Boulton and R. C. Broun, J. Org. Chem.,35, No. 5, 1662–1666 (1970).

    Google Scholar 

  44. I. G. Cadogan, R. Marschall, and M. I. Smith, J. Chem. Soc., C,. No. 18, 2441–24466 (1970).

    Google Scholar 

  45. M. Christudhas, C. P. Ioshua, and P. K. Ramdas, Ind. J. Chem. Sect. B,22b, No. 4, 325–329 (1983).

    Google Scholar 

  46. R. Coombs and G. E. Hardtmann, J. Org. Chem.,35, No. 7, 2440–2444 (1970).

    Google Scholar 

  47. R. Coombs, ibid.,42, No. 10, 1812–1816 (1977).

    Google Scholar 

  48. R. B. Davis and L. C. Pizzini, ibid.,25, 1884–1888 (1960).

    Google Scholar 

  49. T. Doppler, H. Hansen, and H. Schmid, Helv. Chim. Acta,55, No. 5, 1730–1734 (1972).

    Google Scholar 

  50. T. Doppler and H. Schmid, ibid.,62, No. 1, 271–275 (1979).

    Google Scholar 

  51. T. Doppler and H. Schmid, ibid.,62, No. 1, 304–308.

    Google Scholar 

  52. D. R. Eckroth and T. V. Cochran, J. Chem. Soc., C., No. 19, 2660–2666 (1970).

    Google Scholar 

  53. R. A. Finnegan, J. Org. Chem.,30, No. 4, 1333–1335 (1965).

    Google Scholar 

  54. T. Fournari and Marey, Bull. Soc. Chim. Fr., No. 8, 3223–3233 (1968).

    Google Scholar 

  55. M. Georgarakis, T. Doppler, M. Marky, et al., Helv. Chim. Acta,54, No. 8, 2916–2922 (1971).

    Google Scholar 

  56. E. Glovanini, J. Rosales, and B. Souza, ibid.,54, No. 7, 2111–2115.

    Google Scholar 

  57. E. Giovanini and F. S. E. Bernardo, ibid..

    Google Scholar 

  58. E. Giovanini and F. S. E. Bernardo, ibid.,62, No. 1, 198–204.

    Google Scholar 

  59. W. A. Gladstone, J. E. Aulward, and R. O. Nornan, J. Chem. Soc., C., No. 18, 2587–2592 (1969).

    Google Scholar 

  60. I. H. Hall, F. E. Behz, and R. L. Reed, J. Am. Chem. Soc.,94, No. 14, 4952–4955 (1972).

    Google Scholar 

  61. N. F. Haley, J. Org. Chem.,42, No. 24, 3929–3932 (1977).

    Google Scholar 

  62. N. F. Haley, ibid.,43, No. 6, 1233–1237 (1978).

    Google Scholar 

  63. D. G. Hawkins and O. Meth-Cohn, J. Chem. Soc., Perkin Trans. I, No. 9, 1077–1081 (1983).

    Google Scholar 

  64. M. Ionescu and I. Hopartean, Stud. Univ. Babes-Bolyai Ser Chim.,15, No. 1, 77 (970).

  65. C. P. Ioshua and M. Christudhas, Ind. J. Chem.,22B, No. 5, 432–436 (1983).

    Google Scholar 

  66. S. Iacobescu-Ciliann, D. Belu, M. Lazarescu, and I. Neubauer, Rev. Chim.,25, No. 11, 869–872 (1974).

    Google Scholar 

  67. D. Kohwar, R. C. Boruahs, and J. S. Sandhu, Ind. J. Chem.,21B, 899–905 (1982).

    Google Scholar 

  68. D. Kohwar, R. C. Boruahs, and S. Sandhu, ibid.,23B, No. 10, 975–980 (1984).

    Google Scholar 

  69. D. Kohwar, R. C. Boruahs, J. S. Sandhu, and I. N. Boruahs, Synth. Commun.,14, No. 11, 1053–1058 (1984).

    Google Scholar 

  70. D. Kohwar, R. C. Boruahs, and J. S. Sandhu, Heterocycles,23, No. 10, 2557–2560 (1985).

    Google Scholar 

  71. M. Makosza and A. Zielinska, Roczn. Chem.,46, No. 5, 955–960 (1972).

    Google Scholar 

  72. J. Nakagawa, O. Akio, and K. Sirakawa, Chem. Pharm. Bull.,20, No. 10, 2209–2214 (1972).

    Google Scholar 

  73. R. J. Ning, J. F. Blount, and R. J. Fryel, J. Org. Chem.,42, No. 10, 1791–1796 (1977).

    Google Scholar 

  74. J. Nomura, I. Kkiuchi, and I. Takeuchi, Chem. Lett., No. 6, 575–582 (1974).

    Google Scholar 

  75. B. Novak, D. Babic, M. Japely, and V. Tisler, Hern. Ind.,34, No. 12, 330–336 (1980).

    Google Scholar 

  76. L. D. Nunno and S. Florio, Gaz. Chim. Ital.,108, Nos. 11–12, 607–610 (1978).

    Google Scholar 

  77. M. Ogata, H. Kano, and H. Matsumoto, Chem. Commun., No. 7, 397–402 (1968).

    Google Scholar 

  78. M. Ogata, H. Matsumoto, and H. Kano, Tetrahedron,25, No. 21, 5205–5206 (1969).

    Google Scholar 

  79. R. A. Olofson, R. K. Vander Meer, and Stamoulis Stournas, J. Am. Chem. Soc.,93, 1543–1547 (1971).

    Google Scholar 

  80. R. A. Olofson, R. K. Vander Meer, D. H. Hoskin, and M. I. Bernheim, J. Org. Chem.,49, No. 18, 3367–3370 (1984).

    Google Scholar 

  81. I. Panea, J. Hopartean, and M. Jonescu, Stud. Univ. Babes-Bolyai Ser. Chim.,19, No. 2, 30–35 (1974).

    Google Scholar 

  82. J. L. Pinkus, A. Howard, and J. T. Cohen, J. Chem. Soc., C., No. 2, 242–247 (1979).

    Google Scholar 

  83. V. S. Prabhu, Ind. J. Chem.,23B, No. 2, 163–167 (1984).

    Google Scholar 

  84. K. Russel and P. Pranc, J. Org. Chem.,33, No. 7, 2880–2883 (1968).

    Google Scholar 

  85. W. Schäber and H. Schlude, Tetrahdedron Lett., No. 44, 4313–4315 (1967).

    Google Scholar 

  86. R. K. Smalley, R. H. Smith, and H. Suschitzky, ibid., No. 26, 2309–2312 (1978).

    Google Scholar 

  87. R. K. Smalley, R. H. Smith, and H. Suschitzky, ibid., No. 48, 4687–4691 (1979).

    Google Scholar 

  88. A. Streitweiser, G. R. Ziegler, G. H. Mowery, et al., J. Am. Chem. Soc.,90, No. 5, 1357–1362 (1968).

    Google Scholar 

  89. P. Sutter and C. D. Weis, J. Het. Chem.,19, No. 5, 997–1001 (1982).

    Google Scholar 

  90. E. C. Taylor and J. Bartulin, Tetrahedron Lett., No. 25, 2337–2339 (1967).

    Google Scholar 

  91. E. C. Taylor, D. R. Eckroth, and J. Bartulin, J. Org. Chem.,32, No. 6, 1899–1902 (1967).

    Google Scholar 

  92. R. K. Vander Meer and R. A. Olofson, ibid.,49, No. 18, 3373–3376 (1984).

    Google Scholar 

  93. G. N. Walor, ibid.,27, 1929–2932 (1962).

    Google Scholar 

  94. M. Wilk, H. Schwab, and F. Rochlitz, Aunabn. Chem., No. 698, 149–154 (1966).

    Google Scholar 

  95. J. Wrubel and R. Mayer, Z. Chem. (1984).

  96. K. H. Wunsch and A. J. Boulton, Adv. Het. Chem.,8, 277–379 (1967).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Central Chemical Laboratory, S. Ordzhonikidze All-Union Research Institute for Pharmaceutical Chemistry, Moscow

    V. G. Granik, V. M. Pechenina & N. A. Mukhina

  2. Novikuznetsk Research Institute for Pharmacetutical Chemistry, USSR

    V. G. Granik, V. M. Pechenina & N. A. Mukhina

Authors
  1. V. G. Granik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. M. Pechenina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. A. Mukhina
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 25, No. 1, pp. 57–66, January, 1991.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Granik, V.G., Pechenina, V.M. & Mukhina, N.A. 2,1-Bensoidoxazoles [anthranils]. Synthesis and opening of the isoxazole ring (review). Pharm Chem J 25, 48–59 (1991). https://doi.org/10.1007/BF00766367

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00766367

Keywords

Search

Navigation