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2, 3-Polymethylenequinolines and related compounds (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The methods for the synthesis of and the chemical properties and biological activity of 2, 3-polymethylenequinolines and related β-quinindines are reviewed.

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Literature cited

  1. I. F. Tishchenkova, L. E. Kholodov, and V. G. Yashunskii, Khim.-Farmats. Zh., No. 12, 7 (1968).

    Google Scholar 

  2. R. Elderfield and É. Lozin, in: Heterocyclic Compounds, Wiley (1950–1967).

  3. J. H. Markgraf and W. Scott, Chem. Commun., 296 (1967).

  4. J. H. Markgraf, R. J. Katt, W. Scott, and R. N. Shefrin, J. Org. Chem., 34, 4131 (1969).

    Google Scholar 

  5. W. Borsche, Ann., 377, 120 (1910).

    Google Scholar 

  6. W. Borsche, Ber., 41, 2203 (1908).

    Google Scholar 

  7. W. Treibs and G. Kempter, Ber., 92, 601 (1959).

    Google Scholar 

  8. G. Kempter, F. Andrstachke, D. Heilmann, H. Krausmann, and M. Mietsch, Ber., 97, 16 (1964).

    Google Scholar 

  9. G. Kempter and G. Mobius, J. prakt. Chem., 34, 298 (1966).

    Google Scholar 

  10. W. O. Kermack and W. Muir, J. Chem. Soc., 3089 (1931).

  11. W. H. Perkin and W. L. Seigwick, J. Chem. Soc., 438 (1926).

  12. G. Kempter and W. Stoss, Z. Chem., 3, 61 (1963).

    Google Scholar 

  13. I. L. Dibold and M. Wolf, US Patent No. 3649632 (1972); Ref. Zh. Khim., 2N313P (1973).

  14. E. A. Fehnel, J. Org. Chem., 31, 2899 (1966).

    Google Scholar 

  15. W. Borsche and J. Barthenheier, Ann., 548, 50 (1941).

    Google Scholar 

  16. W. Borsche and W. Rottsieper, Ann., 377, 101 (1910).

    Google Scholar 

  17. A. Marino, G. Raffaele, and N. Vito, Ann. Chim. (Roma), 53, 1237 (1963).

    Google Scholar 

  18. V. Petrow, J. Chem. Soc., 693 (1942).

  19. L. J. Sargent and L. F. Small, J. Org. Chem., 19, 140 (1954).

    Google Scholar 

  20. W. Borsche, Ann., 377, 70 (1910).

    Google Scholar 

  21. B. D. Tilak, Berde Hemlata, V. N. Gogte, and T. Ravindranathan, Indian J. Chem., 8, 1 (1970).

    Google Scholar 

  22. V. Petrow, J. Chem. Soc., 634 (1947).

  23. J. M. L. Stephen, J. M. Tonkin, and J. Waiker, J. Chem. Soc., 1034 (1947).

  24. M. E. Dobson, J. Ferns, and W. H. Perkin, J. Chem. Soc., 95, 2015 (1909).

    Google Scholar 

  25. R. J. Brown, F. W. S. Carver, and B. L. Hollingsworth, J. Chem. Soc., 2624 (1962).

  26. W. Bukhsh and R. D. Desai, Proc. Indian Acad. Sci., 10A, 262 (1939).

    Google Scholar 

  27. G. K. Hughes, and F. Lions, Proc. Roy. Soc. N. W. Wales, 71, 458 (1937).

    Google Scholar 

  28. L. J. Sargent and L. Small, J. Org. Chem., 12, 567 (1947).

    Google Scholar 

  29. R. D. Desai and D. V. Shintre, J. Indian Chem. Soc., 33, 425 (1956).

    Google Scholar 

  30. V. M. Sigal, J. B. Brent, and F. Marchini, US Patent No. 3232945 (1966); Ref. Zh. Khim., 4N420P (1968).

  31. S. Coffey, J. K. Tomson, and F. J. Wilson, J. Chem. Soc., 856 (1936).

  32. H. K. Sen and U. Basu, J. Indian. Chem. Soc., 7, 435 (1930).

    Google Scholar 

  33. H. Tiedtke, Ber., 42, 624 (1909).

    Google Scholar 

  34. L. J. Sargent and L. Small, J. Org. Chem., 11, 359 (1946).

    Google Scholar 

  35. R. D. Desai, V. M. Desai, and P. R. Desai, J. Indian Chem. Soc., 37, 553 (1960).

    Google Scholar 

  36. E. D. Pribyl and C. F. Turk, US Patent No. 3318896 (1967); Ref. Zh. Khim., 21N369P (1967).

  37. E. D. Pribyl and C. F. Turk, US Patent No. 3318895 (1967); Ref. Zh. Khim., 14N403P (1969).

  38. R. W. Hinde and W. E. Matthews, Australian Patent No. 266105 (1966); Ref. Zh. Khim., 18N396P (1968).

  39. R. A. Reed, J. Chem. Soc., 425 (1944).

  40. J. Szmuszkovicz, in: Advances in Organic Chemistry [Russian translation], Vol. 4, Mir. Moscow (1966), p. 5.

    Google Scholar 

  41. B. K. Blount, W. G. Perkin, and S. G. Plant, J. Chem. Soc., 1975 (1929).

  42. B. K. Blount and S. G. Plant, J. Chem. Soc., 376 (1937).

  43. A. Albert, R. Gojdacr, and E. Heymann, J. Chem. Soc., 654 (1943).

  44. A. Albert and W. Gledhill, J. Indian Chem. Soc., 22, 169 (1945).

    Google Scholar 

  45. M. E. Konshin, D. I. Uvarov, É. S. Abramochkin, A. S. Zaks, and T. A. Kapitonenko, Khim.-Farmats. Zh., No. 7, 17 (1974).

    Google Scholar 

  46. G. A. Klimov, T. I. Makar'eva, and M. N. Tilichenko, USSR Author's Certificate No. 319596 (1971); Byul. Izobr., No. 33, p. 76 (1971).

  47. E. Hayashi and I. Yamomoto, J. Pharm. Soc. Japan, 87, 1290 (1967); Ref. Zh. Khim., 12Zh291 (1968).

    Google Scholar 

  48. I. A. Moore and L. D. Kornreich, Tetrahedron Lett., 1277 (1963).

  49. M. Lamant, Ann. Chim. (Paris), 4, 87 (1959).

    Google Scholar 

  50. U. Basu and S. J. Das-Gupta, J. Indian Chem. Soc., 14, 468 (1937).

    Google Scholar 

  51. O. Yu. Magidson and A. I. Travin, Zh. Obshch. Khim., 7, 842 (1937).

    Google Scholar 

  52. W. P. Brian and B. L. Souther, J. Med. Chem., 8, 143 (1965).

    Google Scholar 

  53. C. K. Patnaik, M. M. Vohra, J. Bindra, C. F. Gard, and N. Anand, J. Med. Chem., 9, 483 (1966).

    Google Scholar 

  54. É. S. Abramochkin and M. E. Konshin, Zhim.-Farmats. Zh., No. 7, 10 (1970).

    Google Scholar 

  55. M. E. Konshin and E. Ś. Abramochkin, Khim. Geterotsikl. Soedin., 1667 (1970).

  56. M. E. Konshin, É. S. Abramochkin, and D. I. Uvarov, Izv. Vuzov, Ser. Khim., 15, 245 (1972).

    Google Scholar 

  57. D. I. Uvarov, A. S. Zaks, L. G. Zil'bermints, M. E. Konshin, and T. A. Kapitonenko, Khim.-Farmats. Zh., No. 2, 17 (1973).

    Google Scholar 

  58. D. I. Uvarov, M. E. Konshin, A. S. Zaks, L. G. Zil'bermints, and T. A. Kapitonenko, Khim.-Farmats. Zh., No. 8, 25 (1973).

    Google Scholar 

  59. M. E. Konshin and D. I. Uvarov, Khim. Geterotsikl. Soedin., 531 (1973).

  60. J. Braun, A. Heymons, and C. Manz, Ber., 64, 227 (1931).

    Google Scholar 

  61. K. Dziewonski and J. Schoen, Bull. Intern. Acad. Polonaise, A, 448 (1934).

    Google Scholar 

  62. P. A. Petyunin, M. E. Konshin, and Yu. V. Kozhevnikov, Zh. Vsesoyuzn, Khim. Obshchestva, 12, 238 (1967).

    Google Scholar 

  63. M. E. Konshin, Khim. Geterotsikl. Soedin., 974 (1970).

  64. M. E. Konshin, Khim. Geterotsikl. Soedin., 1242 (1970).

  65. M. E. Konshin and P. A. Petyunin, Khim.-Farmats. Zh., No. 11, 10 (1971).

    Google Scholar 

  66. M. E. Konshin, Izv. Vuzov, Ser. Khim., 15, 726 (1972).

    Google Scholar 

  67. M. E. Konshin, Khim. Geterotsikl. Soedin., 528 (1973).

  68. M. E. Konshin, Khim. Geterotsikl. Soedin., 966 (1974).

  69. I. Nagaoka, J. Pharm. Soc. Japan, 81, 479 (1961).

    Google Scholar 

  70. P. I. S. Bur, T. Broadhurst, and A. Robertson, J. Chem. Soc., 2440 (1953).

  71. R. Iyer, A. H. Jackson, P. V. R. Shannon, and B. Naidoo, J. Chem. Soc. Chem. Commun., 461 (1972).

  72. G. E. Calf and E. Richie, Proc. Roy. Soc., 83, 117 (1949).

    Google Scholar 

  73. E. Baciocchi, G. Illuminati, and G. Marino, J. Amer. Chem. Soc., 80, 2270 (1958).

    Google Scholar 

  74. V. Petrow, J. Chem. Soc., 18 (1945).

  75. A. B. Lal and V. Petrow, J. Chem. Soc., 1895 (1948).

  76. L. E. Kholodov and V. G. Yashunskii, Khim. Geterotsikl. Soedin. 1530 (1970).

  77. T. Ozawa, S. Nagaoka, and M. Matsui, J. Pharm. Soc. Japan, 77, 85 (1957); Ref. Zh. Khim., 46799 (1958).

    Google Scholar 

  78. E. Hayashi and T. Nagao, J. Pharm. Soc. Japan, 84, 198 (1964); Ref. Zh. Khim., 4Zh263 (1965).

    Google Scholar 

  79. E. W. Hahn and D. Tomczyk, Roczn. Chem., 46, 837 (1972).

    Google Scholar 

  80. T. A. Klimov and M. N. Tilichenko, Zh. Obshch. Khim., 35, 977 (1965).

    Google Scholar 

  81. H. P. Higgil and S. G. Plant, J. Chem. Soc., 784 (1939).

  82. R. L. Desai and J. N. Ray, J. Indian Chem. Soc., 35, 88 (1958).

    Google Scholar 

  83. E. Hayashi and P. Tomo, J. Pharm. Soc. Japan, 85, 645 (1965); Ref. Zh. Khim., 8Zh277 (1966).

    Google Scholar 

  84. W. G. Perkin and S. G. Plant, J. Chem. Soc., 639 (1928).

  85. W. G. Perkin and W. L. Sed, J. Chem. Soc., 2446 (1924).

  86. D. A. Archer, H. Booth, P. C. Crisp, and J. Parrick, J. Chem. Soc., 330 (1963).

  87. W. F. Lannon, J. Med. Chem., 10, 289 (1967).

    Google Scholar 

  88. V. G. Ermolaeva, V. G. Yashunskii, A. I. Polezhaeva, and M. D. Mashkovskii, Khim.-Farmats. Zh., No. 6, 20 (1968).

    Google Scholar 

  89. W. G. Perkin and S. G. Plant, J. Chem. Soc., 2583 (1928).

  90. M. M. Cartwright and S. G. Plant, J. Chem. Soc., 1898 (1931).

  91. V. Braun, A. Petzold, and A. Schuitheiss, Ber., 56, 1347 (1923).

    Google Scholar 

  92. E. Hayashi and T. Nagao, Japanese Patent No. 16861 (1966); Ref. Zh. Khim., 14N438P (1968).

  93. H. Adkins and H. L. Coonradt, J. Amer. Chem. Soc., 63, 1953 (1941).

    Google Scholar 

  94. W. Borsche and H. Hartmann, 73, 839 (1940).

  95. V. G. Ermolaeva and M. N. Shchukina, Khim.-Farmats. Zh., No. 8, 33 (1971).

    Google Scholar 

  96. E. I. Kagan and B. I. Ardashev, Khim. Geterotsikl. Soedin., 701 (1967).

  97. V. G. Ermolaeva and V. G. Yashunskii, Khim.-Farmats. Zh., No. 11, 13 (1969).

    Google Scholar 

  98. L. E. Kholodov, V. G. Yashunskii, T. M. Shcherbina, A. I. Polezhaeva, and M. D. Mash-kovskii, Khim.-Farmats. Zh., No. 12, 27 (1970).

    Google Scholar 

  99. W. Borsche and R. Manteuffel, Ann., 534, 56 (1938).

    Google Scholar 

  100. M. Los and W. H. Stafford, J. Chem. Soc., 1680 (1959).

  101. B. I. Ardashev and V. P. Gaidzhurova, Khim. Geterotsikl. Soedin., 109 (1969).

  102. D. I. Uvarov and M. E. Konshin, Khim. Geterotsikl. Soedin., 1084 (1973).

  103. V. A. Stonik, G. A. Klimov, V. I. Vysotskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 953 (1969).

  104. J. J. Eisch and F. J. Gadek, J. Org. Chem., 36, 2065 (1971).

    Google Scholar 

  105. L. E. Kholodov, E. M. Peresleni, I. F. Tishchenkova, N. P. Kostyuchenko, and V. G. Yashunskii, Dokl. Akad. Nauk SSSR, 195, 868 (1970).

    Google Scholar 

  106. V. A. Stonik, V. I. Vysotskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 673 (1972).

  107. V. I. Vysotskii, V. A. Stonik, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 984 (1972).

  108. V. G. Ermolaeva and V. G. Yashunskii, Khim. Geterotsikl. Soedin., 1239 (1970).

  109. V. A. Stonik, V. I. Vysotskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 1542 (1970).

  110. M. N. Tilichenko and V. I. Vysotskii, Zh. Obshch. Khim., 32, 84 (1962).

    Google Scholar 

  111. V. I. Vysotskii and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 1080 (1968).

  112. M. N. Tilichenko, V. A. Stonik, and V. I. Vysotskii, Khim. Geterotsikl. Soedin., 570 (1968).

  113. L. E. Kholodov, N. M. Merzlyakova, N. P. Kostyuchenko, and M. N. Shchukina, Khim. Geterotsikl. Soedin., 91 (1971).

  114. I. F. Tishchenkova, L. E. Kholodov, and V. G. Yashunskii, Khim. Geterotsikl. Soedin., 102 (1971).

  115. L. E. Kholodov, G. P. Syrova, and V. G. Yashunskii, Khim. Geterotsikl. Soedin., 96 (1971).

  116. L. E. Kholodov, I. S. Nikolaeva, N. S. Bogdanova, M. N. Shchukina, G. N. Pershin, and V. G. Yashunskii, USSR Author's Certificate No. 249388 (1969); Byul. Izobr., No. 25, 15 (1969).

  117. D. V. Ioffe, and L. S. Éfros, Usp. Khim., 30, 1325 (1961).

    Google Scholar 

  118. G. A. Klimov and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 1, 306 (1967).

    Google Scholar 

  119. G. A. Klimov and M. N. Tilichenko, Zh. Organ. Khim., 2, 1526 (1966).

    Google Scholar 

  120. M. N. Tilichenko and G. A. Klimov, Khim. Geterotsikl. Soedin., 175 (1969).

  121. M. N. Tilichenko and G. A. Klimov, Zh. Organ. Khim., 1, 924 (1965).

    Google Scholar 

  122. G. A. Klimov and M. N. Tilichenko, Zh. Organ. Khim., 2, 1507 (1966).

    Google Scholar 

  123. M. N. Tilichenko and G. A. Klimov, Khim. Geterotsikl. Soedin., 572 (1969).

  124. W. G. Perkin and W. Sedgwick, J. Chem. Soc., 125, 2437 (1924).

    Google Scholar 

  125. M. E. Konshin and É. S. Abramochkin, Khim. Geterotsikl. Soedin., 546 (1972).

  126. É. S. Abramochkin, M. E. Konshin, A. S. Zaks, and L. G. Zil'bermints, Khim.-Farmats. Zh., No. 1, 19 (1972).

    Google Scholar 

  127. M. E. Konshin, D. I. Uvarov, and É. S. Abramochkin, Khim. Geterotsikl. Soedin., 1106 (1974).

  128. I. A. Meschino, US Patent No. 3278538 (1966); Ref. Zh. Khim., 18N397P (1968).

  129. Lee Cheuk-Man, J. Med. Chem., 11, 388 (1968).

    Google Scholar 

  130. V. G. Ermolaeva, N. P. Kostyuchenko, V. G. Yashunskii, and Yu. N. Sheinker, Khim.-Farmats. Zh., No. 5, 19 (1969).

    Google Scholar 

  131. I. F. Tishchenkova, L. E. Kholodov, and V. G. Yashunskii, Khim. Geterotsikl. Soedin., 87 (1971).

  132. L. E. Kholodov, J. F. Tishchenkova (Tischenkova), and V. G. Yashunskii (Yashunski), Tetrahedron Lett., 1535 (1970).

  133. L. E. Kholodov, I. F. Tishchenkova, I. V. Persianova, and V. G. Yashunskii, Reakts. Sposobnost' Organ. Soedin., 6, 1000 (1969).

    Google Scholar 

  134. L. E. Kholodov, I. F. Tishchenkova, and V. G. Yashunskii, USSR Author's Certificate No. 273204 (1970); Byul. Izobr., No. 20, 33 (1970).

  135. L. E. Kholodov and I. F. Tishchenkova, Zh. Organ. Khim., 7, 853 (1971).

    Google Scholar 

  136. L. E. Kholodov, I. F. Tishchenkova, N. S. Bogdanova, I. S. Nikolaeva, and G. N. Pershin, USSR Author's Certificate No. 309603 (1972); Ref. Zh. Khim., 22N296P (1972).

  137. I. F. Tishchenkova and L. E. Kholodov, Khim. Geterotsikl. Soedin., 1384 (1973).

  138. I. F. Tishchenkova, L. E. Kholodov, and V. G. Yashunskii, USSR Author's Certificate No. 330168 (1972); Ref. Zh. Khim., 14N405P (1973).

  139. E. Kloster-Jensen, E. Kovats, A. Eschenmoser, and E. Heilbronner, Helv. Chim. Acta, 39, 1051 (1956).

    Google Scholar 

  140. R. Mayer, Angew. Chem., 69, 481 (1957).

    Google Scholar 

  141. M. Los, I. P. Saksena, and W. H. Stafford, Proc. Chem. Soc., 352 (1957); Ref. Zh. Khim., 4729 (1959).

  142. V. N. Gogte, A. G. Namioshi, and B. D. Tilak, Tetrahedron Lett., 4305 (1971).

  143. I. F. Tishchenkova, L. E. Kholodov, and V. G. Yashunskii, Zh. Vsesoyuzn. Khim. Obshchestva, 15, 576 (1970).

    Google Scholar 

  144. J. J. Eisch and G. Gupta, Tetrahedron Lett., 3273 (1972).

  145. A. Albert and W. Gledhill, J. Soc. Chem. Industr., 169 (1945).

  146. F. H. Shaw and L. A. Bentley, Austral. J. Exptl. Biol. Med. Sci., 31, 573 (1953).

    Google Scholar 

  147. J. S. De La Lende and L. A. Bentley, Austral. J. Exptl. Biol. Med. Sci., 33, 555 (1955).

    Google Scholar 

  148. F. Heilbronn, Acta Chem. Scand., 15, 386 (1961).

    Google Scholar 

  149. F. H. Shaw and L. A. Bentley, Austral. J. Exptl. Biol. Med. Sci., 33, 113 (1955).

    Google Scholar 

  150. F. H. Shaw and L. A. Bentley, Med. J. Austral., 2, 868 (1954).

    Google Scholar 

  151. F. H. Shaw and L. A. Bentley, Nature, 169, 712 (1952).

    Google Scholar 

  152. F. H. Shaw, L. A. Bentley, and S. Gershon, J. Pharm. Pharmacol., 9, 666 (1957).

    Google Scholar 

  153. S. Gershon, Nature, 186, 1072 (1960).

    Google Scholar 

  154. S. Gershon, and F. H. Shaw, J. Pharm. Pharmacol., 10, 638 (1958).

    Google Scholar 

  155. D. W. Downing, Quart. Rev., 16, 133 (1962).

    Google Scholar 

  156. A. V. Zelenin, Interaction of Amino Derivatives of Acridine with Cells [in Russian], Nauka, Moscow (1971), p. 68.

    Google Scholar 

  157. F. Hesse, Arch. Exptl. Pathol. Pharmakol. Naunyn-Schniede bergs, III, 68 (1926).

    Google Scholar 

  158. J. Pohl and F. Hesse, Klin. Wochschr., 4, 344 (1920).

    Google Scholar 

  159. H. Plotnikow, J. Keith, M. Heimann, W. Keith, and C. Perry, Arch. Intern. Pharmacodyn., 146, 106 (1963).

    Google Scholar 

  160. V. Ettel and J. Neumann, Chem. Listy, 51, 1906 (1957).

    Google Scholar 

  161. I. A. Meschino, US Patent No. 3278539 (1966); Ref. Zh. Khim., 13N434P (1968).

  162. I. A. Meschino, US Patent No. 3244720 (1966); Ref. Zh. Khim., 11N442P (1968).

  163. T. V. Moskovkina and M. N. Tilichenko, Khim.-Farmats. Zh., No. 3, 28 (1970).

    Google Scholar 

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The author thanks É. S. Abramochkin for his assistance in the analysis of the literature data and for writing the last part of this review.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 291–305, March, 1975.

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Konshin, M.E. 2, 3-Polymethylenequinolines and related compounds (review). Chem Heterocycl Compd 11, 251–263 (1975). https://doi.org/10.1007/BF00470064

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