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Synthesis of Heterocyclic Compounds Based on Isatoic Anhydrides (2H-3,1-Benzoxazine-2,4-diones). (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data published after 1979 on the chemical transformations of 2H-3,1-benzoxazine-2,4-diones (isatoic anhydrides), leading to the formation of other heterocyclic compounds, are reviewed, classified, and analyzed.

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REFERENCES

  1. G. M. Coppola, Synthesis, 505 (1980).

  2. T. Kappe and W. Stadlbauer, Advances in Heterocyclic Chemistry. 28. Isatoic Anhydrides and their Use in Heterocyclic Chemistry, Academic Press, London, etc. (1981), pp. 231-361.

    Google Scholar 

  3. T. Minami, N. Matsuzaki, Yo. Ohshiro, and T. Agawa, J. Chem. Soc. Perkin Trans. 1, 1731 (1980).

  4. G. M. Coppola, US Patent No. 4212804; Ref. Zh. Khim., 4O128 (1981).

  5. E. Schefczik, French Patent No. 2572072; Chem. Abs., 105, 226351 (1986).

    Google Scholar 

  6. R. C. F. Jones and J. Schofield, J. Chem. Soc. Perkin Trans. 1, 375 (1990).

  7. S. Ceccarelli, A. D'Alessandro, F. Magnante, R. Scuri, and S. Zanarella, Il Farmaco, 48, 1301 (1993).

    Google Scholar 

  8. J. E. Francis, W. D. Cash, B. S. Barbaz, P. S. Bernard, R. A. Lovell, G. C. Mazzenga, R. C. Friedmann, J. L. Hyun, A. F. Braunwalder, R. S. Loo, and D. A. Bennett, J. Med. Chem., 34, 281 (1991).

    Google Scholar 

  9. G. M. Coppola and G. E. Hardtmann, Synthesis, 63 (1980).

  10. J. Reisch and C. O. Usifoh, J. Heterocycl. Chem., 26, 1495 (1989).

    Google Scholar 

  11. R. Chen and R. Bao, Synthesis, 618 (1989).

  12. J. Jesse and H. Kanter, BRD Patent No. 3905242; Chem. Abs., 114, 81838 (1991).

    Google Scholar 

  13. R. W. Leiby, J. Heterocycl. Chem., 21, 1825 (1984).

    Google Scholar 

  14. Ch. Reddy, P. S. N. Reddy, and C. V. Patnam, Indian J. Chem., 27B, 568 (1988).

    Google Scholar 

  15. J. S. Davidson, Monatsh. Chem., 115, 565 (1984).

    Google Scholar 

  16. J. Padmaja, M. S. Reddy, and C. V. Ratnam, Indian J. Chem., 26B, 951 (1987).

    Google Scholar 

  17. G. M. Coppola, J. Heterocycl. Chem., 19, 727 (1982).

    Google Scholar 

  18. Sh.-Ch. Kuo, H.-Z. Lee, J.-P. Juang, Y.-T. Lin, T.-Sh. Wu, J.-J. Chang, D. Lednicer, K. D. Paull, Ch. M. Lin, E. Hamel, and K.-H. Lee, J. Med. Chem., 36, 1146 (1993).

    Google Scholar 

  19. G. M. Coppola, J. Heterocycl. Chem., 22, 491 (1985).

    Google Scholar 

  20. G. M. Coppola, J. Heterocycl. Chem., 23, 1717 (1986).

    Google Scholar 

  21. G. M. Coppola, J. Heterocycl. Chem., 29, 1873 (1992).

    Google Scholar 

  22. G. M. Coppola, Synthesis, 81 (1988).

  23. G. M. Coppola, Synth. Commun., 18, 995 (1988).

    Google Scholar 

  24. G. M. Coppola, E. Hanover, T. J. Scallen, A. Del Perte, and R. Montano, Heterocycles, 29, 1497 (1989).

    Google Scholar 

  25. G. M. Coppola and H. Schuster, J. Heterocycl. Chem., 26, 957 (1989).

    Google Scholar 

  26. R. K. Russell, C. E. van Nievelt, R. A. Rampulla, D. N. Klaubert, and S. C. Bell, Synthesis, 753 (1992).

  27. G. M. Coppola, J. Heterocycl. Chem., 21, 1569 (1984).

    Google Scholar 

  28. G. M. Coppola, J. Heterocycl. Chem., 21, 913 (1984).

    Google Scholar 

  29. M. Susse and S. Johne, Z. Chem., 25, 432 (1985).

    Google Scholar 

  30. S. J. Kesten, M. J. Degnan, J. Hung, D. J. McNamara, D. F. Ortwine, S. Uhlendorf, and L. M. Werbel, J. Med. Chem., 35, 3429 (1992).

    Google Scholar 

  31. M. Susse and S. Johne, DDR Patent No. 237835;Chem. Abs., 108, 21733 (1988).

    Google Scholar 

  32. S. Radl, Coll. Czech. Chem. Commun., 60, 2127 (1995).

    Google Scholar 

  33. B. Venugopalan, C. P. Bapat, E. P. de Souza, and N. J. de Souza, Indian J. Chem., 31B, 35 (1992).

    Google Scholar 

  34. G. M. Coppola, Synth. Commun., 15, 135 (1985).

    Google Scholar 

  35. G. M. Coppola, J. Heterocycl. Chem., 20, 1217 (1983).

    Google Scholar 

  36. G. M. Coppola, J. Heterocycl. Chem., 22, 1087 (1985).

    Google Scholar 

  37. G. M. Coppola, Synthesis, 939 (1983).

  38. H. Hayashi, Yo. Miwa, Sh. Ichikawa, N. Yoda, I. Miki, A. Ishii, M. Kono, T. Yasuzawa, and F. Suzuki, J. Med. Chem., 36, 617 (1993).

    Google Scholar 

  39. M. P. Wentland, J. A. Carson, P. H. Dorff, S. C. Aldous, R. B. Perni, D. C. Young, M. G. Woods, S. D. Kingsley, K. A. Ryan, D. Rosi, M. L. Drozd, and F. J. Dutko, J. Med. Chem., 38, 2541 (1995).

    Google Scholar 

  40. P. Albaugh, US Patent No. 5 1822 90; Chem. Abs., 119, 49380 (1993).

    Google Scholar 

  41. F. Suzuki, T. Kuroda, Yo. Nakasato, H. Manabe, K. Ohmori, Sh. Kitamura, Sh. Ichikawa, and T. Ohno, J. Med. Chem., 35, 4045 (1992).

    Google Scholar 

  42. G. E. Hardtman, US Patent No. 4292876; Ref. Zh. Khim., 22 O145 (1980).

    Google Scholar 

  43. F. Suzuki, T. Kurora, T. Kawakita, H. Manabe, Sh. Kitamura, K. Ohmori, M. Ichimura, H. Kase, and Sh. Ichikawa, J. Med. Chem., 35, 4866 (1992).

    Google Scholar 

  44. Th. Kappe, M. Hariri, and E. Pongratz, Monatsh. Chem., 112, 1211 (1981).

    Google Scholar 

  45. B. Th. O'Neill, EPV 370686; Chem. Abs., 113, 191182 (1990).

    Google Scholar 

  46. M. P. Wentland, R. B. Perni, P. H. Dorff, R. P. Brundage, M. J. Castaldi, Th. R. Bailey, Ph. M. Carabateas, E. R. Bacon, D. C. Young, M. G. Woods, D. Rosi, M. L. Drozd, R. K. Kullnig, and F. J. Dutko, J. Med. Chem., 36, 1580 (1993).

    Google Scholar 

  47. T. Minami, M. Ogata, and I. Hirao, Synlett, 231 (1982).

  48. G. M. Coppola, R. E. Damon, and G. E. Hardtmann, Synthesis, 391 (1981).

  49. A. Alfonso, J. Weinstein, and M. J. Gentles, US Patent No.5190956; Chem. Abs., 119, 28016 (1993).

    Google Scholar 

  50. G. E. Hardtmann, US Patent No. 4190659; Chem. Abs., 93, 95134 (1980).

    Google Scholar 

  51. M. Matsuo, K. Tsuji, K. Nakamura, and G. W. Spears, PDT WO 9218483; Chem. Abs., 118, 212903 (1993).

    Google Scholar 

  52. L. Vacek, US Patent No. 4362876; Chem. Abs., 98, 107180 (1983).

    Google Scholar 

  53. G. M. Coppola, E. W. Fu, M. J. Shapiro, and G. E. Hardtmann, J. Heterocycl. Chem., 20, 1427 (1983).

    Google Scholar 

  54. A. A. Santilli, US Patent No. 4266050; Ref. Zh. Khim., 3O118 (1982).

  55. R. V. Davies and R. D. Green, EPV 135367; Chem. Abs., 103, 104975 (1985).

    Google Scholar 

  56. A. M. Birch, R. V. Davies, L. Maclean, and K. Robinson, J. Chem. Soc. Perkin Trans. I, 387 (1994).

  57. G. M. Coppola, J. Heterocycl. Chem., 21, 769 (1984).

    Google Scholar 

  58. G. M. Coppola and H. F. Schuster, J. Heterocycl. Chem., 21, 1409 (1984).

    Google Scholar 

  59. H. M. Mack, E. A. Davis, B. Kadkhodayan, R. A. Taylor, D. C. Duncan, and Ch. F. Beam, J. Heterocycl. Chem., 24, 1733 (1987).

    Google Scholar 

  60. D. J. Le Count, J. Chem. Soc. Perkin Trans. I, 813 (1983).

  61. G. M. Coppola, J. Heterocycl. Chem., 17, 1785 (1980).

    Google Scholar 

  62. M. Matsuo, K. Tsuji, G. W. Spears, and T. Tojo, British Patent No. 2290786; Chem. Abs., 124, 289281 (1996).

    Google Scholar 

  63. N. J. Leonard, P. Kamierczak, and A. Rykowski, J. Org. Chem., 52, 2933 (1987).

    Google Scholar 

  64. J. B. Hynes, Y. C. S. Yang, J. E. McGill, S. J. Harmon, and W. L. Washtier, J. Med. Chem., 27, 232 (1984).

    Google Scholar 

  65. Sh. K. Singh, M. Govidan, and J. B. Hynes, J. Heterocycl. Chem., 27, 2101 (1990).

    Google Scholar 

  66. Th. M. Stevenson, F. Kazmierczak, and N. J. Leonard, J. Org. Chem., 51, 616 (1986).

    Google Scholar 

  67. M. Susse and S. Johne, Monatsh. Chem., 118, 71 (1987).

    Google Scholar 

  68. J. A. Grosso, D. E. Nichols, J. D. Kohl, and D. Glock, J. Med. Chem., 25, 703 (1982).

    Google Scholar 

  69. J. A. Grosso and D. E. Nichols, J. Med. Chem., 23, 1261 (1980).

    Google Scholar 

  70. M. A. Hussain, A. T. Chiu, W. A. Price, P. B. Timmermans, and E. Shefter, Pharm. Res., 5, 242 (1988); Chem. Abs.,109, 222 (1988).

    Google Scholar 

  71. S. Leistner, H. Vieweg, G. Wagner, D. Lohmann, and G. Laban, DDR Patent No. 293810; Chem. Abs., 116, 128951 (1992).

    Google Scholar 

  72. S. Leistner, H. Veiweg, G. Wagner, Th. Strohscheidt, D. Lohmann, and G. Laban, DDR Patent No. 293809; Chem. Abs., 116, 83692 (1992).

    Google Scholar 

  73. A. Siodzava, Yu. Itikawa, and T. Takahira, Jpn. Patent No. 135469; Ref. Zh. Khim., 17 O83 (1988).

    Google Scholar 

  74. V. R. K. Reddy, P. S. N. Reddy, and C. V. Ratnam, Indian J. Chem., 30B, 927 (1991).

    Google Scholar 

  75. M. Susse and S. Johne, J. Pr. Chem., 326, 342 (1984).

    Google Scholar 

  76. P. R. Bhalla and B. L. Walworth, US Patent No. 4331440; Chem. Abs., 100, 174857 (1984).

    Google Scholar 

  77. M. Gal, E. Tihanyi, and P. Dvortsak, Heterocycles, 22, 1985 (1984).

    Google Scholar 

  78. N. P. Peet, Synthesis, 1065 (1984).

  79. M. Susse and S. Johne, Monatsh. Chem., 117, 499 (1986).

    Google Scholar 

  80. M. Susse and S. Johne, Z. Chem., 23, 406 (1983).

    Google Scholar 

  81. S. E. Webber, T. M. Beckman, J. Attard, J. G. Deal, V. Kathardekar, K. M. Welsh, S. Webber, Ch. A. Janson, D. A. Matthews, W. W. Smith, S. T. Freer, S. R. Jordan, R. J. Bacquet, E. F. Howland, C. L. Booth, R. W. Ward, S. M. Hermann, J. White, C. A. Morse, J. A. Hilliard, and Ch, A, Bartlett, J. Med. Chem., 36, 733 (1993).

    Google Scholar 

  82. Ch. K. Reddy, P. S. N. Reddy, and C. V. Ratnam, Indian J. Chem., 26B, 882 (1987).

    Google Scholar 

  83. Y. S. Sadanandam, K. R. M. Reddy, and A. Bh. Rao, Eur. J. Med. Chem., 22, 169 (1987).

    Google Scholar 

  84. J. Bergman, U. Tilstam, and K. W. Toernroos, J. Chem. Soc. Perkin Trans. 1, 519 (1987).

  85. R. Domanig, Arch. Pharm., 314, 271 (1981).

    Google Scholar 

  86. L. A. Mitscher, W.-Ch. Wong, T. De Meulenaere, J. Sulko, and S. Drake, Heterocycles, 15, 1017 (1981).

    Google Scholar 

  87. J. Bergman, J.-O. Lundstrom, and U. Tilstam, Tetrahedron, 41, 2879 (1985).

    Google Scholar 

  88. G. Seybold and G. Wagenblast, BRD Patent No. 4114990; Chem. Abs., 119, 10457 (1993).

    Google Scholar 

  89. L. C. Sircar, Th. Capiris, and S. J. Kesten, J. Heterocycl. Chem., 18, 117 (1981).

    Google Scholar 

  90. H. Kanter and B. Ort, EPV 306876; Chem. Abs., 111, 134184 (1989).

    Google Scholar 

  91. H. Kanter and B. Ort, EPV 306866; Chem. Abs., 111, 134185 (1989).

    Google Scholar 

  92. J. C. Sircar, Th. Capiris, and S. J. Kesten, J. Med. Chem., 24, 735 (1981).

    Google Scholar 

  93. K. Seifert, S. Haertling, and S. Johne, DDR Patent No. 154897; Chem. Abs., 98, 16915 (1983).

    Google Scholar 

  94. K. Seifert, S. Haertling, and S. Johne, DDR Patent No. 154897; Chem. Abs., 98, 16915 (1983).

    Google Scholar 

  95. N. P. Peet, L. E. Baugh, Sh. Sunder, J. E. Lewis, E. H. Matthews, E. L. Olberding, and D. N. Shah, J. Med. Chem., 29, 2403 (1986).

    Google Scholar 

  96. M. Susse, A. Schaks, and S. Johne, DDR Patent No. 206778; Chem. Abs., 101, 72752 (1984).

    Google Scholar 

  97. W. B. Wright, A. S. Tomcufcik, P. S. Chan, J. W. Marsico, and J. B. Press, J. Med. Chem., 30, 2277 (1987).

    Google Scholar 

  98. W. B. Wright and A. S. Tomcufcik, US Patent No. 4710502; Ref. Zh. Khim., 17O86 (1988).

  99. M. Susse and S. Johne, DDR Patent No. 232268; Ref. Zh. Khim., 18O416 (1986).

  100. M. Susse and S. Johne, Helv. Chim. Acta, 68, 892 (1985).

    Google Scholar 

  101. M. Susse and S. Johne, J. Pr. Chem., 326, 1027 (1984).

    Google Scholar 

  102. M. Beugelmans-Verrier and P. Portier, Tetrahedron Lett., 43, 3465 (1987).

    Google Scholar 

  103. N. P. Peet and Sh. Sunder, J. Heterocycl. Chem., 21, 1807 (1984).

    Google Scholar 

  104. M. J. Kornet, T. Varia, and W. Beaven, J. Heterocycl. Chem., 20, 1553 (1983).

    Google Scholar 

  105. H. Takai, H. Obase, M. Teranishi, A. Karasawa, K. Kybo, K. Shuto, Yu. Kasuyo, and K. Shigeobu, Chem. Pharm. Bull., 34, 1907 (1986).

    Google Scholar 

  106. M. Susse and S. Johne, DDR Patent No. 151308; Chem. Abs., 96, 162734 (1982).

    Google Scholar 

  107. S. Leistner, M. Guetschow, K. Drossler, G. Wagner, D. Lohmann, and G. Laban, DDR Patent No. 293811; Chem. Abs., 83691 (1992).

  108. M. Guetschow, S. Leistner, E. Tonew, G. Wagner, and D. Lohmann, DDR Patent No. 293812; Chem. Abs., 117, 48586 (1992).

    Google Scholar 

  109. M. J. Kornet, T. Varia, and W. Beaven, J. Heterocycl. Chem., 21, 1533 (1984).

    Google Scholar 

  110. B. Balzac, Jpn. Patent No. 81 128771; Chem. Abs., 96, 104275 (1982).

    Google Scholar 

  111. R. Baronnet, R. Callendret, and L. Blanchard, Eur. J. Med. Chem.-Chim. Ther., 18, 241 (1983).

    Google Scholar 

  112. M. S. Malamas and J. Millen, J. Med. Chem., 34, 1492 (1991).

    Google Scholar 

  113. R. Iemura, M. Hori, T. Saito, and H. Ohtaka, Chem. Pharm. Bull., 37, 2723 (1989).

    Google Scholar 

  114. K.-Ch. Liu and M.-K. Hu, Arch. Pharm., 320, 166 (1987).

    Google Scholar 

  115. H. K. Gakhar, S. C. Gupta, and N. Kumar, Indian J. Chem., 20B, 14 (1981).

    Google Scholar 

  116. H. K. Gakhar, A. Sharma, and Sh. Bh. Gupta, Indian J. Chem., 21B, 456 (1982).

    Google Scholar 

  117. F. Billon, Ch. Delchambre, A. Cloarec, E. Sartori, and J.-M. Teulon, Eur. J. Med. Chem., 25, 121 (1990).

    Google Scholar 

  118. M. Susse and S. Hohne, Z. Chem., 25, 367 (1985).

    Google Scholar 

  119. R. R. Webb, P. L. Barker, M. Baier, M. E. Reynolds, K. D. Robarge, B. K. Blackburn, M. H. Tischer, and K. J. Weese, Tetrahedron Lett., 35, 2113 (1994).

    Google Scholar 

  120. M. Susse, S. Johne, and A. Schaks, DDR Patent No. 232699; Ref. Zh. Khim., 19O95 (1986).

  121. M. Susse, A. Schaks, J. Schmidt, and S. Johne, DDR Patent No. 252827; Chem. Abs., 109, 38258 (1988).

    Google Scholar 

  122. G. M. Coppola, and M. J. Shapiro, J. Heterocycl. Chem., 17, 1163 (1980).

    Google Scholar 

  123. Ch. F. Beam, B. Kadhodayan, R. A. Taylor, and N. D. Heindel, Synth. Commun., 23, 237 (1993); Chem. Abs., 118, 213019 (1993).

    Google Scholar 

  124. R. Cortez, I. A. Rivero, R. Somanathan, G. Aguirre, F. Ramirez, and E. Hong, Synth. Commun., 21, 285 (1991).

    Google Scholar 

  125. K. Inoe, T. Oine, Yo. Yamada, R. Ishida, and T. Ochiai, Jpn Patent No. 60178817; Chem. Abs., 104, 109677 (1986).

    Google Scholar 

  126. M. Rolf and R. Neeft, BRD Patent No. 3401574; Chem. Abs., 103, 197375 (1985).

    Google Scholar 

  127. W. B. Wright, A. S. Tomcufcik, and J. W. Marsio, US Patent No. 4680293; Chem. Abs., 107, 217653 (1987).

    Google Scholar 

  128. M. Susse and S. Johne, Z. Chem., 26, 250 (1986).

    Google Scholar 

  129. M. Susse and S. Johne, Z. Chem., 26, 166 (1986).

    Google Scholar 

  130. M. Susse, A. Schaks, and S. Johne, DDR Patent No. 232271; Ref. Zh. Khim., 18O415 (1986).

  131. M. Susse, S. Johne, and A. Schaks, DDR Patent No. 232703; Ref. Zh. Khim., 19O98 (1986).

  132. M. Susse, A. Schaks, J. Schmidt, and S. Johne, DDR Patent No. 241076; Chem. Abs., 107, 115607 (1987).

    Google Scholar 

  133. S. Narasimhan, Heterocycles, 18, 133 (1982).

    Google Scholar 

  134. P. Canonne, R. Boulanger, and M. Bernatchez, Tetrahedron, 45, 2525 (1989).

    Google Scholar 

  135. A. Krantz, R. W. Spencer, T. F. Tam, T. J. Liak, L. J. Copp, E. M. Thomas, and S. P. Rafferty, J. Med. Chem., 33, 464 (1990).

    Google Scholar 

  136. I. Butula, V. Vela, and B. Zorc, Croat. Chem. Acta, 54, 105 (1981).

    Google Scholar 

  137. Teijin Ltd., Jpn Patent No. 59 12952; Chem. Abs., 101, 8206 (1984).

    Google Scholar 

  138. Agency of Industrial Sciences and Technology, Jpn Patent No. 59 39893; Chem. Abs., 101, 151864 (1984).

    Google Scholar 

  139. E. Hahn, G. Glas, and P. Guenthert, BRD Patent No. 4101380; Chem. Abs., 117, 1714 62 (1992).

    Google Scholar 

  140. B. Boutevin, L. R. Rasoloarijao, A. Rousseau, J. Garapon, and B. Sillion, J. Fluor. Chem., 58, 29 (1992); Chem. Abs., 117, 251301 (1992).

    Google Scholar 

  141. J. Bergman and S. Bergman, Heterocycles, 16, 347 (1981).

    Google Scholar 

  142. J. Bergman and S. Bergman, J. Org. Chem., 50, 1246 (1985).

    Google Scholar 

  143. Y. R. Rao, M. Bapuji, and S. M. Mahapatra, Indian Patent No. 150839; Chem. Abs., 99, 158452 (1983).

    Google Scholar 

  144. M. Lancaster, Pat. PCT WO 93 22300; Chem. Abs., 120, 107039 (1994).

    Google Scholar 

  145. S. Leistner, K. Hentschel, and G. Wagner, Z. Chem., 23, 215 (1983).

    Google Scholar 

  146. B. R. Shinde, S. J. Shenoy, and N. R. Pai, Indian J. Chem., 29B, 711 (1990).

    Google Scholar 

  147. M. Gates, J. Org. Chem., 45, 1675 (1980).

    Google Scholar 

  148. G. Mohinddin, P. S. N. Reddy, Kh. Akhmed, and C. V. Ratnam, Indian J. Chem., 24B, 905 (1985).

    Google Scholar 

  149. Z.-Q. Gu, G. Wong, C. Dominguez, B. R. de Costa, K. C. Rice, and Ph. Skolnick, J. Med. Chem., 36, 1001 (1993).

    Google Scholar 

  150. P. Zhang, W. Zhang, R. Liu, B. Harris, Ph. Skolnick, and J. M. Cook, J. Med. Chem., 38, 1697 (1995).

    Google Scholar 

  151. W. Haefely, W. Hunkeler, E. Kyburz, H. Moehler, L. Pieri, P. Pole, and M. Gerecke, EPV 27214; Chem. Abs., 95, 115621 (1981).

    Google Scholar 

  152. W. Hunkeler and E. Kyburz, EPV 59386; Chem. Abs., 98, 53948 (1983).

    Google Scholar 

  153. F. Watjen, J. B. Jansen, M. J. Engelstoft, and H. Leif, Can. Pat. No. 1266671; Chem. Abs., 113, 212029 (1990).

    Google Scholar 

  154. M. K. Kukla, H. J. Breslin, C. J. Diamond, Ph. P. Grous, Ch. Y. Ho, M. Miranda, J. D. Rodgers, R. G. Sherill, E. De Clercq, R. Pauwels, K. Andries, L. J. Moens, M. A. C. Janssen, and P. A. J. Janssen, J. Med. Chem., 34, 3187 (1991).

    Google Scholar 

  155. S. Ananthan, S. D. Clayton, S. E. Ealick, G. Wong, G. E. Evoniuk, and Ph. Scolnick, J. Med. Chem., 36, 479 (1993).

    Google Scholar 

  156. D. A. Claremon and N. Liverton, Pat. PCT WO 94 22825; Chem. Abs., 122, 56059 (1995).

    Google Scholar 

  157. M. G. Bock, B. E. Evans, R. M. Freidinger, and S. M. Pitzenberger, US Patent No. 4594191; Chem. Abs., 105, 133917 (1986).

    Google Scholar 

  158. M. G. Bock, R. M. Di Pardo, S. M. Pitzenberger, C. F. Homnick, J. P. Springer, and R. M. Freidinger, J. Org. Chem., 52, 1644 (1987).

    Google Scholar 

  159. B. Bhat and D. M. Harrison, Tetrahedron, 49, 10655 (1993).

    Google Scholar 

  160. B. Bhat and D. M. Harrison, Tetrahedron Lett., 27, 5873 (1986).

    Google Scholar 

  161. M. Susse, A. Schaks, and S. Johne, DDR Patent No. 249475; Chem. Abs., 108, 131865 (1988).

    Google Scholar 

  162. M. Oklobdzija, E. Decorte, G. Comiso, T. Fajdia, G. Gratton, F. Moimas, R. Reso, and V. Sunjic, J. Heterocycl. Chem., 20, 1329 (1983).

    Google Scholar 

  163. W. Hunkeler and E. Kyburz, EPV 59387; Chem. Abs., 98, 72146 (1983).

    Google Scholar 

  164. W. Hunkeler and E. Kyburz, EPV 100906; Chem. Abs., 101, 7217 (1984).

    Google Scholar 

  165. J. W. Suggs, Yu.-Sh. Wang, and K. S. Lee, Tetrahedron Lett., 26, 4871 (1985).

    Google Scholar 

  166. A. G. Schultz, P. J. McCloskey, and J. J. Court, J. Am. Chem. Soc., 109, 6493 (1987).

    Google Scholar 

  167. T. Nagasaka, Yu. Keseki, and F. Hamaguchi, Tetrahedron Lett., 30, 1871 (1989).

    Google Scholar 

  168. A. Kamal, J. Org. Chem., 56, 2237 (1991).

    Google Scholar 

  169. J. N. Reed and V. Snieckus, Tetrahedron Lett., 25, 5505 (1984).

    Google Scholar 

  170. M. R. Pena and J. K. Stille, J. Am. Chem. Soc., 111, 5417 (1989).

    Google Scholar 

  171. H. J. Breslin, M. J. Kukla, D. W. Ludovici, R. Mohrbacher, W. Ho, M. Miranda, J. D. Rodgers, T. K. Hitchens, G. Leo, D. A. Gauthier, Ch. Y. Yo, M. K. Scott, E. De Clercq, R. Pauwels, K. Andries, M. A. C. Janssen, and P. A. J. Janssen, J. Med. Chem., 38, 771 (1995).

    Google Scholar 

  172. M. R. Pena and J. K. Stille, Tetrahedron Lett., 28, 6573 (1987).

    Google Scholar 

  173. A. Kamal and D. E. Thurston, Tetrahedron Lett., 30, 6221 (1989).

    Google Scholar 

  174. H. Hulinska, Z. Polivka, J. Jilek, K. Sindelar, J. Holubek, E. Svatek, O. Matousova, M. Budesinsky, H. Frycova, and M. Protiva, Coll. Czech. Chem. Commun., 53, 1820 (1988).

    Google Scholar 

  175. K. Cooper, M. J. Fray, and J. Stelle, Pat. PCT WO 92 00978; Chem. Abs., 116, 174178 (1992).

    Google Scholar 

  176. J. B. Press, C. M. Hofmann, and S. R. Safir, J. Heterocycl. Chem., 17, 1361 (1980).

    Google Scholar 

  177. B. J. Borrell, S. J. Rocas, and G. E. Fernandez, Spanish Patent No. 548906; Chem. Abs., 106, 84661 (1987).

    Google Scholar 

  178. H. Matsumura, H. Hashizume, A. Matsushita, and M. Eigyo, EPV 353778; Chem. Abs., 113, 40740 (1990).

    Google Scholar 

  179. F. Watjen and H. C. Hansen, EPV 283162; Chem. Abs., 110, 57685 (1989).

    Google Scholar 

  180. G. M. Coppola, J. Heterocycl. Chem., 20, 1589 (1983).

    Google Scholar 

  181. H. K. Gakhar, R. Gupta, and J. K. Gill, Indian J. Chem., 25B, 957 (1986).

    Google Scholar 

  182. J. P. Demers and R. B. Sulsky, US Patent No. 4904667; Chem. Abs., 113, 59212 (1990).

    Google Scholar 

  183. K. Ch. Liu, M. K. Hu, and Yu. O. Lin, Chung-hua Yao Hsueh Tsa Chin, 42, 83 (1990); Chem. Abs., 114, 23910 (1991).

    Google Scholar 

  184. T. O. Olagbemiro, Bull. Soc. Chim. Belg., 90, 1067 (1981).

    Google Scholar 

  185. H. Takahata, N. Hamada, and T. Yamazaki, Synthesis, 388 (1986).

  186. W. Hunkeler and E. Kyburz, EPV 59390; Chem. Abs., 98, 53949 (1983).

    Google Scholar 

  187. W. Hunkeler and E. Kyburz, EPV 59391; Chem. Abs., 98, 53950 (1983).

    Google Scholar 

  188. L. Bruche and G. Zecchi, Tetrahedron, 45, 7427 (1989).

    Google Scholar 

  189. H. Neunhoeffer, J. Hansa, and H. Hammann, Annalen, 640 (1985).

  190. G. Broggini, L. Bruche, L. Garanti, and G. Zecchi, J. Chem. Soc. Perkin Trans 1, 433 (1994).

    Google Scholar 

  191. H. K. Gakhar, A. Jain, J. K. Grill, and Sh. Bh. Gupta, Monatsh. Chem., 114, 339 (1983).

    Google Scholar 

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  1. A. N. Kosygin Moscow State Textile Academy, Moscow, Russia

    M.-G. A. Shvekhgeimer

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Shvekhgeimer, MG.A. Synthesis of Heterocyclic Compounds Based on Isatoic Anhydrides (2H-3,1-Benzoxazine-2,4-diones). (Review). Chemistry of Heterocyclic Compounds 37, 385–443 (2001). https://doi.org/10.1023/A:1017631318971

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