Skip to main content
Log in

2-Quinazolinones and their cyclic homologs (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods for the synthesis of 2-quinazolinones, 1,2-dihydro-3H-1,4-benzodiazepin-2-ones, 1,2,3,4-tetrahydro-1,5-benzodiazocin-2-ones, and 1,2,3,4-tetrahydro-5H-1,6-benzodiazonin-2-ones are examined along with the peculiarities of their structure, their tautomerism, their chemical properties, and their biological activity.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. L. Sternbach, L. Randall, and S. Gustafson, Psychopharmacological Agents, Vol. 1, Academic Press, New York (1964), p. 137.

    Google Scholar 

  2. J. Moore and E. Mitchell, in: R. Elderfield (ed.) Heterocyclic Compounds, Vol. 9, New York (1967), p. 225.

  3. G. Archer and L. Sternbach, Chem. Rev., 68, 751 (1968).

    Google Scholar 

  4. A. V. Bogat-skii and S. A. Andronati, Usp. Khim., 39, 2217 (1970).

    Google Scholar 

  5. S. Garattini, E. Mussini, and L. Randall (eds.), The Benzodiazepines, Raven Press, New York (1973).

    Google Scholar 

  6. R. Elderfield (ed.), Heterocyclic Compounds, Vol. 6, Wiley.

  7. W. L. F. Armarego, Quinazolines, Interscience Publ., New York-London-Sydney (1967).

    Google Scholar 

  8. A. Bischler, Ber., 26, 1891 (1893).

    Google Scholar 

  9. K. Auwers and E. Frese, Ann., 450, 273 (1926).

    Google Scholar 

  10. A. Stempel, J. Douvan, and L. Sternbach, J. Org. Chem., 33, 2963 (1968).

    Google Scholar 

  11. T. Sulkowski, US Patent No. 3294782 (1966); Ref. Zh. Khim., 19N409P (1968).

  12. A. V. Bogat-skii, S. A. Andronati, O. P. Rudenko, Z. I. Zhilina, and I. A. Starovoit, Summaries of Papers Presented at the Twelfth Ukrainian Republical Conference on Organic Chemistry [in Russian], Uzhgorod (1974), p. 54.

  13. H. Yamamoto, S. Inaba, T. Okamoto, T. Kirobashi, K. Ishizumi, M. Yamamoto, I. Maruyana, K. Mori, and T. Kobayashi, Japanese Patent No. 4176 (1971); Ref. Zh. Khim., 22N424P (1971).

  14. S. Gabriel and T. Posner, Ber., 28, 1029 (1895).

    Google Scholar 

  15. S. Gabriel and R. Stelzner, Ber., 29, 1300 (1896).

    Google Scholar 

  16. G. Stefanović, L. Lorenc, and M. L. Mihailović, Bull. Acad. Serbe Sci. et Arts, 26, 119 (1961); Ref. Zh. Khim., 9Zh242 (1962).

    Google Scholar 

  17. R. Coombs, R. Danna, N. Denzer, G. Hardtman, B. Huegi, G. Koletar, J. Koletar, and H. Ott, J. Med. Chem., 16, 1237 (1973).

    Google Scholar 

  18. A. V. Bogat-skii, S. A. Andronati, Z. I. Zhilina, and N. I. Danilina, Zh. Org. Khim., 13, 1773 (1977).

    Google Scholar 

  19. I. Ya. Postovskii, O. N. Chupakhin, T. L. Pilicheva, N. A. Klyuev, and S. L. Mertsalov, Zh. Org. Khim., 11, 875 (1975).

    Google Scholar 

  20. H. Ott, USSR Patent No. 354656 (1972); Ref. Zh. Khim., 3N337P (1974).

  21. S. Inaba, M. Yamamoto, K. Ishizumi, K. Mori, and H. Yamamoto, Japanese Patent No. 29517 (1972); Ref. Zh. Khim., 22N387P (1973).

  22. M. Yamamoto, K. Ishizumi, K. Mori, S. Inaba, and H. Yamamoto, Japanese Patent No. 49-46632 (1974); Ref. Zh. Khim., 210165P (1975).

  23. S. Inaba, M. Yamamoto, K. Ishizumi, K. Mori, and H. Yamamoto, Japanese Patent No. 17792 (1972); Ref. Zh. Khim., 7N433P (1973).

  24. S. Inaba, M. Yamamoto, K. Ishizumi, K. Mori, and H. Yamamoto, Japanese Patent No. 48-21953 (1973); Ref. Zh. Khim., 11N277P (1974).

  25. S. Inaba, M. Yamamoto, K. Ishizumi, K. Mori, and H. Yamamoto, Japanese Patent No. 21429 (1972); Ref. Zh. Khim., 10N348P (1973).

  26. S. Inaba, M. Yamamoto, K. Ishizumi, K. Mori, and H. Yamamoto, USSR Patent No. 403180 (1973); Ref. Zh. Khim., 4083P (1975).

  27. K. Ishizumi, S. Inaba, and H. Yamamoto, J. Org. Chem., 38, 2617 (1973).

    Google Scholar 

  28. K. Ishizumi, S. Inaba, and H. Yamamoto, J. Org. Chem., 39, 2587 (1974).

    Google Scholar 

  29. M. Yamamoto, K. Ishizumi, K. Mori, M. Oshiba, S. Inaba, and H. Yamamoto, Japanese Patent No. 49-46633 (1974); Ref. Zh. Khim., 18L181P (1975).

  30. H. Ott, Swiss Patent No. 499545 (1970); Ref. Zh. Khim., 15N468P (1971).

  31. M. Yamamoto, K. Ishizumi, K. Mori, M. Koshiba, S. Inaba, and H. Yamamoto, Japanese Patent No. 48-8628 (1973); Ref. Zh. Khim., 3N338P (1974).

  32. H. Ott, SSR Patent No. 53491 (1972); Ref. Zh. Khim., 7N325P (1974).

  33. T. Komatsu, H. Awata, Y. Sakai, T. Inukai, M. Yamamoto, S. Inaba, and H. Yamamoto, Arzneimittel. Forsch., 22, 1958 (1972).

    Google Scholar 

  34. K. W. Brenkink and P. E. Verkade, Rec. Trav. Chim., 79, 443 (1960).

    Google Scholar 

  35. R. C. Elderfield and I. Serlin, J. Org. Chem., 16, 1669 (1951).

    Google Scholar 

  36. M. T. Bogert and C. E. May, J. Am. Chem. Soc., 31, 507 (1909).

    Google Scholar 

  37. T. Higashino, J. Pharm. Soc. Jpn., 79, 699 (1959).

    Google Scholar 

  38. E. Hayashi, H. Yamanaka, and T. Higashino, Chem. Pharm. Bull. (Tokyo), 7, 149 (1959).

    Google Scholar 

  39. E. Hayashi and T. Higashino, Chem. Pharm. Bull. (Tokyo), 12, 43 (1964).

    Google Scholar 

  40. O. G. Hardtman, US Patent No. 3563990 (1971); Ref. Zh. Khim., 20N427P (1971).

  41. Sandoz, Irish Patent No. 33177 (1974); Ref. Zh. Khim., 150199P (1975).

  42. K. Ishizumi, S. Inaba, and H. Yamamoto, J. Org. Chem., 39, 2581 (1974).

    Google Scholar 

  43. S. Bell, T. Sulkowski, C. Gochman, and S. Childress, J. Org. Chem., 27, 562 (1962).

    Google Scholar 

  44. G. Walker, J. Org. Chem., 27, 1929 (1962).

    Google Scholar 

  45. L. Sternbach, R. Fryer, W. Metlesics, E. Reeder, G. Sach, G. Sausy, and A. Stempel, J. Org. Chem., 27, 3788 (1962).

    Google Scholar 

  46. A. Stempel, and F. Landgraf, J. Org. Chem., 27, 4675 (1962).

    Google Scholar 

  47. C. Podesva and E. Cullen, British Patent No. 1063891 (1967); Ref. Zh. Khim., 16N411P (1968).

  48. R. McCaully, US Patent No. 3899527 (1975); Ref. Zh. Khim., 100124P (1976).

  49. G. F. Field and L. H. Sternbach, Swiss Patent No. 561705 (1975); Ref. Zh. Khim., 10164P (1975); Ref. Zh. Khim., 10164P (1976).

  50. R. McCaully, US Patent No. 3763171 (1973); Ref. Zh. Khim., 17N450P (1974).

  51. N. Blazević and F. Kajfež, J. Heterocycl. Chem., 7, 1173 (1970).

    Google Scholar 

  52. P. Nedenskov and K. Alster, British Patent No. 1313642 (1973); Ref. Zh. Khim., 22N393P (1973).

  53. M. Shindo, K. Moro, and T. Shinozaki, US Patent No. 3692776 (1972); Ref. Zh. Khim., 14N411P (1973).

  54. S. Bell, US Patent No. 3468878 (1969); Ref. Zh. Khim., 21N396P (1970).

  55. H. Yamamoto, S. Inaba, T. Hiroyuki, M. Akatsu, I. Kume, K. Mori, M. Yamamoto, T. Izumi, K. Ishizumi, and N. Maruyama, Japanese Patent No. 3827 (1972); Ref. Zh. Khim., 4N428P (1973).

  56. H. Yamamoto, S. Inaba, T. Hirohashi, M. Yamamoto, H. Sentaku, M. Akatsu, K. Ishiguroki, I. Maruyama, R. Kume, and K. Mori, Japanese Patent No. 1928-1931 (1972); Ref. Zh. Khim., 17N276P–17N279P (1972).

  57. F. Kajfež and N. Blazević, Swiss Patent No. 547293 (1974); Ref. Zh. Khim., 21N433P (1974).

  58. H. Yamamoto, S. Inaba, T. Hirohashi, and K. Ishizumi, Chem. Ber., 101, 4245 (1968).

    Google Scholar 

  59. S. Inaba, T. Hirohashi, and H. Yamamoto, Chem. Pharm. Bull. (Tokyo), 17, 1263 (1969).

    Google Scholar 

  60. H. Yamamoto, S. Inaba, T. Hirohashi, K. Ishiguro, and I. Maruyama, Japanese Patent No. 35906 (1970); Ref. Zh. Khim., 19N508P (1971).

  61. H. Yamamoto, S. Inaba, T. Okamoto, T. Hirohashi, K. Ishiguro, M. Yamamoto, I. Maruyami, K. Mori, and T. Kobayashi, Japanese Patent No. 28287 (1970); Ref. Zh. Khim., 19N506P (1971).

  62. S. Inaba, M. Akatsu, and H. Yamamoto, Japanese Patent No. 13916 (1972); Ref. Zh. Khim., 12N364P (1973).

  63. H. Yamamoto, S. Inaba, and K. Ishizumi, Japanese Chem. Ind. Assoc. Mon., 28, 694 (1975); Ref. Zh. Khim., 20Zh261 (1976).

    Google Scholar 

  64. K. Schöfield and R. S. Theobald, J. Chem. Soc., No.4, 796 (1949).

    Google Scholar 

  65. R. Fryer and L. Sternbach, US Patent No. 3376290 (1968); Ref. Zh. Khim., 1N501P (1970).

  66. Clin-Byla, Dutch Patent No. 6507637 (1965); Chem. Abstr., 64, 15902 (1966).

    Google Scholar 

  67. H. Tawada, H. Natsugari, K. Megyro, and Y. Kuwada, US Patent No. 3746701 (1973); Ref. Zh. Khim., 13N368P (1974).

  68. E. Römer, Swiss Patent No. 498128 (1970); Ref. Zh. Khim., 12N575P (1971).

  69. T. Masuda and I. Kamai, Japanese Patent No. 34436 (1971); Ref. Zh. Khim., 16N279P (1972).

  70. R. Davis and L. Pizzini, J. Org. Chem., 25, 1884 (1960).

    Google Scholar 

  71. O. Aki, Y. Takagawa, K. Sidakawa, and M. Yamamoto, Japanese Patent No. 48-21114 (1973); Ref. Zh. Khim., 12N333P (1974).

  72. Y. Nakagawa, O. Aki, K. Sirakawa, Chem. Pharm. Bull. (Tokyo), 20, 2209 (1972); Ref. Zh. Khim., 8Zh402 (1973).

    Google Scholar 

  73. J. Hellerbach, W. Metlesics, and L. Sternbach, US Patent No. 3297685 (1967); Ref. Zh. Khim., 14N444P (1968).

  74. A. Stempel, J. Douvan, E. Reeder, and L. Sternbach, J. Org. Chem., 32, 2417 (1967).

    Google Scholar 

  75. P. Sorentino, UAR Patent No. 6706791 (1968); Chem. Abstr., 70, 57916 (1968).

    Google Scholar 

  76. Hoffmann-La Roche, Austrian Patent No. 311363 (1973); Ref. Zh. Khim., 23N434P (1974).

  77. K. Meguro and Y. Kuwada, J. Pharm. Soc. Jpn., 93, 1263 (1973).

    Google Scholar 

  78. R. I. Fryer, G. A. Archer, B. Brust, W. Zally, and L. H. Sternbach, J. Org. Chem., 30, 1308 (1965).

    Google Scholar 

  79. S. Inaba, T. Okamoto, T. Hirohashi, K. Ishizumi, M. Yamamoto, J. Maruyama, K. Mori, T. Kobayashi, and H. Yamamoto, US Patent No. 3666643 (1972); Ref. Zh. Khim., 6N445P (1973).

  80. A. M. Felix, J. V. Earley, R. I. Fryer, and L. H. Sternbach, J. Heterocycl. Chem., 5, 731 (1968).

    Google Scholar 

  81. W. Milkowski, S. Funke, R. Hünschens, H. G. Liepmann, W. Stühmer, and H. Zeugner, West German Patent Application No. 2221536 (1973); Ref. Zh. Khim., 20N459P (1974).

  82. K. Meguro and Y. Kuwada, Chem. Pharm. Bull. (Tokyo), 21, 2375 (1973).

    Google Scholar 

  83. T. Tatikawa, H. Takaki, T. Kamioka, M. Fukunaga, and I. Kawano, Japanese Patent No. 47-29970 (1972); Ref. Zh. Khim., 5N360P (1974).

  84. J. Röhricht, L. Kisfaludy, M. Löw, J. Szakolszay, and L. Dancsi, Hungarian Patent No. 160768 (1973); Ref. Zh. Khim., 19N416P (1974).

  85. L. Sternbach and E. Reeder, J. Org. Chem., 26, 4936 (1961).

    Google Scholar 

  86. A. Stempel, E. Reeder, and L. Sternbach, J. Org. Chem., 30, 4267 (1965).

    Google Scholar 

  87. L. Schlager, Austrian Patent No. 308753 (1973); Ref. Zh. Khim., 6N315P (1974).

  88. S. Bell, R. McCaully, and S. Childress, J. Med. Chem., 33, 2889 (1965).

    Google Scholar 

  89. R. McCaully, US Patent No. 3926952 (1975); Ref. Zh. Khim., 170164P (1976).

  90. R. McCaully, US Patent No. 3875213 (1975); Ref. Zh. Khim., 30151P (1976).

  91. R. McCaully, US Patent No. 3873604 (1975); Ref. Zh. Khim., 40125P (1976).

  92. M. Derieg, R. Schweininger, and R. Fryer, J. Org. Chem., 34, 179 (1969).

    Google Scholar 

  93. A. V. Bogat-skii, A. V. Ben'ko, and S. A. Andronati, Dokl. Akad. Nauk Ukr. SSR, No. 9, 801 (1977).

    Google Scholar 

  94. M. Steinman and T. Topliss, J. Pharmac. Sci., 58, 830 (1969).

    Google Scholar 

  95. M. Denzer and H. Ott, J. Org. Chem., 34, 183 (1969).

    Google Scholar 

  96. S. A. Andronati, O. P. Rudenko, and A. V. Bogat-skii, Zh. Obshch. Khim., 45, 389 (1975).

    Google Scholar 

  97. S. A. Andronati, A. V. Bogat-skii, Yu. I. Vikhlyaev, Z. I. Zhilina, B. M. Kats, T. A. Klygul', V. N. Khudyakova, T. K. Chumachenko, and A. A. Énnan, Zh. Obshch. Khim., 40, 1881 (1970).

    Google Scholar 

  98. A. V. Bogat-skii, S. A. Andronati, O. P. Rudenko, and P. B. Terent'ev, Summaries of Papers Presented at the First All-Union Conference on the Chemistry of Heterocyclic Compounds (Nitrogen Heterocycles) [in Russian], Chernogolovka (1973), p. 22.

  99. S. F. Mason, J. Chem. Soc., No. 12, 4874 (1957).

    Google Scholar 

  100. T. I. Korotenko, A. V. Bogat-skii, S. A. Andronati, Z. I. Zhilina, I. A. Starovoit, V. I. Sidorov, and A. F. Galatin, in: Problems in Stereochemistry [in Russian], Vol. 5, Vishcha Shkola, Kiev-Odessa (1976), p. 135.

    Google Scholar 

  101. S. A. Andronati, in: Problems in Stereochemistry [in Russian], Vol. 3, Vischa Shkola, Kiev-Odessa (1973), p. 3.

    Google Scholar 

  102. A. V. Bogat-skii, S. A. Andronati, Yu. Yu. Samitov, A. I. Galatina, E. V. Konovalov, E. P. Saenko, and S. G. Soboleva, Khim. Geterotsikl. Soedin., No. 6, 838 (1974).

    Google Scholar 

  103. P. Linsheid and J. Lehn, Bull. Soc. Chim. Fr., No. 3, 992 (1967).

    Google Scholar 

  104. W. Bley, P. Nuhn, and G. Benndorf, Arch. Pharm., 301, 444 (1968).

    Google Scholar 

  105. W. Sadee, Arch. Pharm., 302, 769 (1969).

    Google Scholar 

  106. A. Kamerman and H. Kamerman, J. Am. Chem. Soc., 94, 268 (1972).

    Google Scholar 

  107. M. Sarrazin, M. Bourdeaux-Pontier, and E. Vincent, Org. Magn. Reson., 7, 89 (1975).

    Google Scholar 

  108. T. I. Korotenko, V. S. Yur'eva, A. V. Bogat-skii, V. I. Minkin, S. A. Andronati, L. E. Nivorozhkin, and L. N. Yakubovskaya, Summaries of Papers Presented at the Third All-Union Conference on Stereochemistry and Conformational Analysis in Organic and Petro-chemical Synthesis [in Russian], Baku-Sumgant (1976), p. 49.

  109. A. V. Bogat-skii, V. I. Minkin, S. A. Andronati, V. S. Yur'eva, T. I. Korotenko, L. N. Yakubovskaya, A. I. Galatina, and L. E. Nivorozhkin, Summaries of Papers Presented at the All-Union Conference on the Synthesis and Mechanism of the Effect of Physiologically Active Substances [in Russian], Odessa (1976), p. 9.

  110. A. V. Bogat-skii, S. A. Andronati, T. I. Korotenko, L. N. Yakubovskaya, V. I. Minkin, V. S. Yur'eva, and L. E. Nivorozhkin, in: Problems in Stereochemistry [in Russian], Vol. 6, Vishcha Shkola, Kiev-Odessa (1977), p. 74.

    Google Scholar 

  111. V. Sunjić, M. Stromar, F. Kajfež, S. Rendić, and D. Kolbah, Acta Pharm. Jugosl., 23, 213 (1973).

    Google Scholar 

  112. V. Sunjić, F. Kajfež, J. Stromar, N. Blazević, and D. Kolbah, J. Heterocycl. Chem., 10, 591 (1973).

    Google Scholar 

  113. V. Sunjić, J. Kuftines, and F. Kajfež, Arzneimittel-Forsch., 25, 340 (1975).

    Google Scholar 

  114. A. V. Bogat-skii, S. A. Andronati, Yu. I. Vikhlyaev, Z. I. Zhilina, T. A. Klygul', and V. F. Ryakhin, Khim.-Farm. Zh., No. 5, 13 (1974).

    Google Scholar 

  115. A. Albert and J. N. Phillips, J. Chem. Soc., No. 6, 1294 (1956).

    Google Scholar 

  116. S. L. Mertsalov, L. G. Egorova, and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., No. 5, 687 (1970).

    Google Scholar 

  117. A. V. Bogat-skii, S. A. Andronati, Z. I. Zhilina, O. P. Rudenko, I. A. Starovoit, and T. K. Chumachenko, Zh. Obshch. Khim., 42, 2571 (1972).

    Google Scholar 

  118. R. Fryer, J. Earley, and L. Sternbach, J. Org. Chem., 32, 3798 (1967).

    Google Scholar 

  119. S. A. Andronati, Yu. I. Vikhlyaev, T. A. Klygul', and A. V. Bogat-skii, in: Physiologically Active Substances [in Russian], Vol. 5, Naukova Dumka, Kiev (1973), p. 117.

    Google Scholar 

  120. J. Earley, R. Fryer, D. Winter, and L. Sternbach, J. Med. Chem., 11, 774 (1968).

    Google Scholar 

  121. M. Derieg, R. Fryer, R. Schweininger, and L. Sternbach, J. Med. Chem., 11, 912 (1968).

    Google Scholar 

  122. A. Albert and G. B. Barlin, J. Chem. Soc., No. 8, 3129 (1968).

    Google Scholar 

  123. E. Reeder and L. Sternbach, US Patent No. 3247186 (1966); Ref. Zh. Khim., 3N418P (1968).

  124. S. Christenscu, British Patent No. 1247554 (1971); Ref. Zh. Khim., 7N375P (1972).

  125. G. Hardtmann and H. Ott, US Patent No. 3547921 (1970); Ref. Zh. Khim., 16N444P (1971).

  126. R. Y. R. Ning and L. Sternbach, US Patent No. 3801569 (1974); Ref. Zh. Khim., 30129P (1975).

  127. F. McEvoy, E. Greenblatt, H. Osterberg, and G. Allen, J. Med. Chem., 11, 1248 (1968).

    Google Scholar 

  128. H. Piper, G. Krüger, J. Keck, and R. Noll, West German Patent Application No. 2311714 (1974); Ref. Zh. Khim., 110276P (1975).

  129. G. Hanscke, Ber., 32, 2021 (1899).

    Google Scholar 

  130. A. V. Bogat-skii, S. A. Andronati, E. D. Sych, T. K. Chumachenko, Z. I. Zhilina, V. N. Khudyakova, Yu. I. Vikhlyaev, T. A. Klygul', and A. A. Énnan, Summaries of Papers Presented at the Tenth Ukrainian Republican Conference on Organic Chemistry [in Russian], Kiev (1969), p. 76.

  131. S. Bell and S. Childress, J. Org. Chem., 27, 1591 (1962).

    Google Scholar 

  132. S. Bell, R. McCaully, C. Gochman, S. Childress, and M. Gluckman, J. Med. Chem., 11, 457 (1968).

    Google Scholar 

  133. S. Bell, US Patent No. 3296249 (1967); Ref. Zh. Khim., 18N407P (1968).

  134. A. Walser, G. Silverman, and R. Fryer, J. Org. Chem., 38, 3502 (1973).

    Google Scholar 

  135. R. Moffet and A. Rudzik, J. Med. Chem., 16, 1256 (1973).

    Google Scholar 

  136. S. Inaba, M. Yamamoto, K. Ishizumi, and K. Mori, Japanese Patent No. 48-21951 (1973); Ref. Zh. Khim., 11N275P (1974).

  137. A. V. Bogat-skii, Z. I. Zhilina, N. I. Danilina, and I. A. Starovoit, Summaries of Papers Presented at the All-Union Conference on the Synthesis and Mechanism of the Effect of Physiologically Active Substances [in Russian], Odessa (1976), p. 33.

  138. H. Oelschläger, J. Volke, and E. Kurek, Arch. Pharm., 297, 431 (1964).

    Google Scholar 

  139. H. Oelschläger, J. Volke, G. T. Lim, and R. Spang, Arch. Pharm., 302, 946 (1969).

    Google Scholar 

  140. A. V. Bogat-skii, S. A. Andronati, V. P. Gul'tyai, Yu. I. Vikhlyaev, A. F. Galatin, Z. I. Zhilina, and T. A. Klygul', Zh. Obshch. Khim., 41, 1358 (1971).

    Google Scholar 

  141. S. A. Andronati, A. V. Bogat-skii, V. P. Gul'tyai, T. A. Klygul', S. P. Smul'skii, and Yu. I. Vikhlyaev, in: Physiologically Active Substances [in Russian], Vol. 7, Naukova Dumka, Kiev (1975), p. 75.

    Google Scholar 

  142. L. Sternbach, E. Reeder, and G. Archer, J. Org. Chem., 28, 2456 (1963).

    Google Scholar 

  143. K. Ishizumi, K. Mori, T. Okamoto, T. Okasa, I. Izumi, M. Akatsu, Y. Kume, S. Inaba, and H. Yamamoto, US Patent No. 3880575 (1975); Ref. Zh. Khim., 30148P (1976).

  144. K. Ishiguro, K. Mori, T. Okamoto, T. Anase, T. Izumi, M. Akatsu, I. Kume, S. Inaba, and H. Yamamoto, Japanese Patent No. 50-11396 (1975); Ref. Zh. Khim., 90165P (1976).

  145. L. H. Sternbach, R. I. Fryer, O. Keller, W. Metlesics, G. Sach, and N. Steiger, J. Med. Chem., 6, 261 (1963).

    Google Scholar 

  146. A. Walser, G. Zenchoff, and R. I. Fryer, J. Med. Chem., 19, 1378 (1976).

    Google Scholar 

  147. H. Roth, and M. Adomeit, Arch. Pharm., 306, 889 (1973).

    Google Scholar 

  148. H, Oelschläger, J. Volke, G. T. Lim, and U. Frank, Arzneimit, Forsch., 16, 82 (1966).

    Google Scholar 

  149. H. Oelschläger, J. Volke, and G. T. Lim, Arch. Pharm., 302, 241 (1969).

    Google Scholar 

  150. J. Hromas and A. Nováćek, Czechoslovakian Inventor's Certificate No. 150806 (1973); Ref. Zh. Khim., 60155P (1976).

  151. J. Hellerbach and A. Walser, Australian Patent No. 433500 (1973); Ref. Zh. Khim., 11N289P (1974).

  152. Aktiengeselskabet Grinstedvaerket, Dutch Patent No. 6608039 (1966); Chem. Abstr., 66, 105006 (1967).

    Google Scholar 

  153. A. Walser and J. Hellerbach, Swiss Patent No. 500996 (1971); Ref. Zh. Khim., 18N447P (1972).

  154. T. S. Sulkowski and S. J. Childress, J. Org. Chem., 28, 2150 (1963).

    Google Scholar 

  155. R. Ning and L. Sternbach, US Patent No. 3682892 (1972); Ref. Zh. Khim., 12N345P (1973).

  156. A. V. Bogat-skii, V. V. Danilin, S. A. Andronati, O. P. Rudenko, P. B. Terent'ev, and P. A. Sharbatyan, Summaries of Papers Presented at the All-Union Conference on the Synthesis and Mechanism of the Effect of Physiologically Active Substances [in Russian], Odessa (1976), p. 48.

  157. G. Sauchy and L. Sternbach, Helv. Chim. Acta, 45, 2226 (1962).

    Google Scholar 

  158. J. Hellerbach and A. Walser, Swiss Patent 503750 (1971); Ref. Zh. Khim., 19N504P (1971).

  159. R. Ning and L. Sternbach, US Patent No. 3627754 (1971); Ref. Zh. Khim., 19N305P (1972).

  160. A. V. Bogat-skii, N. Ya. Golovenko, S. A. Andronati, G. Yu. Kolomeichenko, and V. G. Zin'kovskii, Dokl. Akad. Nauk Ukr. SSR, Ser. B, No. 8, 740 (1975).

    Google Scholar 

  161. H. Yamamoto, S. Inaba, O. Wada, S. Hagino, and F. Kishimoto, Japanese Patent No. 50-11999 (1975); Ref. Zh. Khim., 130143P (1976).

  162. R. I. Fryer, B. Brust, and L. H. Sternbach, J. Chem. Soc., No. 10, 4977 (1963).

    Google Scholar 

  163. R. I. Fryer, I. V. Earley, and L. H. Sternbach, J. Org. Chem., 30, 521 (1965).

    Google Scholar 

  164. J. Sellstedt, US Patent No. 3882101 (1975); Ref. Zh. Khim., 80190P (1976).

  165. Clin-Byla, French Patent No. 1455048 (1966); Chem. Abstr., 66, 95096 (1967).

    Google Scholar 

  166. J. Schmitt, Australian Patent No. 414082 (1971); Ref. Zh. Khim., 11N352P (1973).

  167. A. Ziggiotti, G. Riva, and F. Mauri, British Patent Nos. 1333501 and 1333502 (1973); Ref. Zh. Khim., 12N336P and 12N337P (1974).

  168. R. Ning and L. Sternbach, US Patent No. 3635948 (1972); Ref. Zh. Khim., 2N318P (1973).

  169. Hoffmann-La Roche, Austrian Patent No. 309452 (1973); Ref. Zh. Khim., 13N367P (1974).

  170. Hoffmann-La Roche, UAR Patent No. 66/7088 (1967) (cited in an earlier review [3]).

  171. J. Sellstedt, J. Org. Chem., 40, 1508 (1975).

    Google Scholar 

  172. E. Poetsch, J. Uhn, D. Marx, W. Strehlow, H. Müller-Calgan, and G. Dolce, West German Patent Application No. 2460360 (1976); Ref. Zh. Khim., 80123P (1977).

  173. R. Ning and L. Sternbach, US Patent No. 3801569 (1974); Ref. Zh. Khim., 30129P (1975).

  174. W. Metlesics, R. Tavares, and L. Sternbach, J. Org. Chem., 30, 1311 (1965).

    Google Scholar 

  175. S. Bell, US Patent No. 3198789 (1965); Ref. Zh. Khim., 10N303P (1967).

  176. S. Bell, US Patent No. 3401159 (1969); Ref. Zh. Khim., 4N463P (1970).

  177. S. Bell, US Patent No. 3418315 (1969); Ref. Zh. Khim., 11N619P (1970).

  178. R. Ning, L. Sternbach, W. Pool, and L. Randall, J. Med. Chem., 16, 879 (1973).

    Google Scholar 

  179. R. Ning and L. Sternbach, US Patent No. 3644334 (1972); Ref. Zh. Khim., 22N311P (1973).

  180. H. Natsukari, K. Meguro, K. Tsuzigawa, and H. Kuwada, Japanese Patent No. 48-12757 (1973); Ref. Zh. Khim., 9N282P (1974).

  181. G. Archer and L. Sternbach, J. Org. Chem., 29, 231 (1964).

    Google Scholar 

  182. J. Hester, US Patent No. 3674777 (1972); Ref. Zh. Khim., 6N444P (1973).

  183. G. Archer and L. Sternbach, US Patent No. 3422091 (1969); Ref. Zh. Khim., 9N433P (1970).

  184. J. B. Hester, J. Rudzik, D. Allan, and B. V. Kamdar, J. Med. Chem., 14, 1078 (1971).

    Google Scholar 

  185. S. Inaba, M. Yamamoto, K. Ishizumi, K. Mori, and H. Yamamoto, Japanese Patent No. 48-8117 (1973); Ref. Zh. Khim., 12N326P (1974).

  186. H. Yamamoto, Y. Nakamura, S. Inaba, and I. Maruyama, Japanese Patent No. 20911 (1970); Ref. Zh. Khim., 16N460P (1971).

  187. M. Derieg, J. Earley, I. Fryer, R. Schweininger, L. Sternbach, and H. Wharton, Tetrahedron, 27, 2591 (1971).

    Google Scholar 

  188. R. Janin, W. Oberhäusli, and I. Hellerbach, Helv. Chim. Acta, 55, 2975 (1972).

    Google Scholar 

  189. J. Szmuskowicz, C. Chidester, D. Duchamp, and F. Mackeller, Tetrahedron Lett., No. 39, 3665(1971).

    Google Scholar 

  190. J. Hester, US Patent No. 3714178 (1973); Ref. Zh. Khim., 1N311P (1973).

  191. Z. I. Zhilina, A. V. Bogat-skii, T. K. Sych, T. K. Chumachenko, and S. A. Andronati, Khim. Geterotsikl. Soedin., No.7, 992 (1971).

    Google Scholar 

  192. A. V. Bogat-skii, S. A. Andronati, Z. I. Zhilina, O. V. Kobzareva, P. A. Sharbatyan, R. Yu. Ivanova, and T. K. Chumachenko, Zh. Obshch. Khim., 45, 396 (1975).

    Google Scholar 

  193. H. Pieper, G. Krüger, J. Keck, and K. Noll, West German Patent Application No. 2304095 (1974); Ref. Zh. Khim., 120252 (1975).

  194. J. Dobresky, B. Gonzabz, and A. Molinari, Rev. Acad. Bioquim. Argent., 36, 214 (1971).

    Google Scholar 

  195. L. Schlager, Austrian Patent No. 309436 (1973); Ref. Zh. Khim., 50155P (1975).

  196. I. Grecu and P. Marcu, Farmacia (RSR), 21, 339 (1973).

    Google Scholar 

  197. R. Fryer, J. Heterocycl. Chem., 9, 747 (1972).

    Google Scholar 

  198. S. Bell, P. Valley, and H. Wei, US Patent No. 3563990 (1971); Ref. Zh. Khim., 20N427P (1972).

  199. Yu. I. Vikhlyaev and T. A. Voronina, New Medicinals. Express Information [in Russian], VNIIMI, Moscow (1978), No. 3, p. 2.

    Google Scholar 

  200. G. M. Rudenko, N. G. Shatrova, and V. K. Lepakhin, New Medicinals. Express Information [in Russian], VNIIMI, Moscow (1978), No. 3, p. 7.

    Google Scholar 

  201. M. P. de la Mora, K. Fuxe, F. Luigi, T. Hökfeit, and A. Ljungdahl, Abstracts of Papers Presented at the Sixth International Congress of Pharmacology, Helsinki (1975), p. 400.

  202. S. Bredstrup, R. Albrechtsen, and R. F. Ckuires, Nature, 269, 702 (1977).

    Google Scholar 

  203. A. V. Bogat-skii, Yu. I. Vikhlyaev, S. A. Andronati, T. A. Klygul', T. K. Chumachenko, and Z. I. Zhilina, Khim.-Farm. Zh., No. 4, 5 (1970).

    Google Scholar 

  204. A. V. Bogat-skii, Yu. I. Vikhlyaev, S. A. Andronati, T. A. Klygul', and Z. I. Zhilina, Khim. Geterotsikl. Soedin., No. 11, 1558 (1973).

    Google Scholar 

  205. A. V. Bogat-skii, S. A. Andronati, T. A. Klygul', Z. I. Zhilina, Yu. I. Vikhlyaev, and R. Yu. Ivanova, Khim.-Farm. Zh., No. 2, 37 (1977).

    Google Scholar 

  206. A. V. Bogat-skii, S. A. Andronati, Yu. I. Vikhlyaev, T. A. Voronina, L. N. Yakubovskaya, and A. V. Ben'ko, Khim.-Farm. Zh., No. 11, 85 (1977).

    Google Scholar 

  207. S. P. Smul'skii, A. V. Bogat-skii, S. A. Andronati, Yu. I. Vikhlyaev, and Z. I. Zhilina, Dokl. Akad. Nauk SSSR, 235, 369 (1977).

    Google Scholar 

  208. Yu. I. Vikhlyaev, A. V. Bogat-skii, T. A. Klygul', S. A. Andronati, O. P. Rudenko, and P. B. Terent'ev, in: Physiologically Active Substances [in Russian], Vol. 6, Naukova Dumka, Kiev (1974), p. 94.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 723–738, June, 1979.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bogat-skii, A.V., Andronati, S.A. 2-Quinazolinones and their cyclic homologs (review). Chem Heterocycl Compd 15, 583–597 (1979). https://doi.org/10.1007/BF00539490

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00539490

Keywords

Navigation