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Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

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Pharmaceutical Chemistry Journal Aims and scope

The main trends in the development of the chemistry of α-, γ-, and δ-carbolines are generalized. Syntheses of carbolines based on pyridine derivatives (including the Fischer synthesis, Graebe—Ullmann reaction, thermal decomposition of azides, photochemical cyclization of anilinopyridines, arylation of substituted pyridines and piperidones, etc.) and based on indole derivatives are described. Published data about the biological activity of compounds belonging to these series are summarized.

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Notes

  1. Neurodegenerative diseases (degenerative diseases of the nervous system) represent a large group of related diseases caused by massive progressive neuron death. The neurodegenerative process for AD is associated with progressive memory loss and reduced mental and intellectual capacity with subsequent slow progressive dementia.

References

  1. V. I. Dulenko, I. V. Komisarov, A. T. Dolzhenko, and Yu. A. Nikolyukin, β-Carbolines. Chemistry and Neurobiology [in Russian], Naukova Dumka, Kiev (1992).

    Google Scholar 

  2. R. Elderfield, ed., Heterocyclic Compounds, Vol. 6: Six-membered Heterocycles Containing Two Heteroatoms and Their Benzo Derivatives, Wiley, New York (1957).

    Google Scholar 

  3. R. A. Abramovitch and I. D. Spencer, Adv. Heterocycl. Chem., 3, 79 – 207 (1964).

    PubMed  CAS  Google Scholar 

  4. A. N. Kost, M. A. Yurovskaya, and F. A. Trofimov, Khim. Geterotsikl. Soedin., No. 3, 291 – 305 (1973).

  5. A. A. Semenov and V. V. Tolstikhin, Khim. Geterotsikl. Soedin., No. 4, 435 – 447 (1984).

  6. R. S. Alekseev, A. F. Kurkin, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., No. 8, 1123 – 1166 (2009).

  7. M. D. Mashkovskii, Drugs [in Russian], Torsing, Kharkov (1997).

    Google Scholar 

  8. V. G. Granik, Drugs: Pharmacological, Biochemical, and Chemical Aspects [in Russian], Vuzovskaya Kniga, Moscow (2001).

    Google Scholar 

  9. S. O. Bachurin, Vopr. Med. Khim., No. 2, 1 – 21 (2001).

  10. Yu. Ya. Ivanov, A. Z. Afanas?ev, and S. O. Bachurin, Khim.-farm. Zh., 35, No. 7, 7 – 8 (2001).

    Google Scholar 

  11. RF Pat. No. 2,106,864; http://www1.fips.ru.

  12. R. D. Clark, A. B. Miller, J. Berger, et al., J. Med. Chem., 36(18), 2645 – 2657 (1993).

    PubMed  CAS  Google Scholar 

  13. RF Pat. No. 2,002,748; http://www1.fips.ru.

  14. WO Pat. No. 9917755; http://ep.espacenet.com.

  15. EP Pat. No. 0306323; http://ep.espacenet.com.

  16. WO Pat. No. 0048597; http://ep.espacenet.com.

  17. N. N. Suvorov, V. A. Chernov, V. S. Velezheva, et al., Khim.-farm. Zh., 15(9), 27 – 34 (1981).

    CAS  Google Scholar 

  18. E. Arzel, P. Rocca, P. Grellier, et al., J. Med. Chem., 44, No. 6, 949 – 960 (2001).

    PubMed  CAS  Google Scholar 

  19. K. Bonjean, M. C. Pauw-Gillet, M. P. Defresne, et al., Biochemistry, 37(15), 5136 – 5146 (1998).

    PubMed  CAS  Google Scholar 

  20. C. Moquin-Pattey and M. Guyot, Tetrahedron, 45(11), 3445 – 3450 (1989).

    CAS  Google Scholar 

  21. K. Cimanga, T. Bruyne, L. Pieters, et al., Tetrahedron Lett., 37(10), 1703 – 1706 (1996).

    CAS  Google Scholar 

  22. D. W. Nagel, K. G. R. Pachler, P. S. Steyn, et al., Tetrahedron, 32(21), 2625 – 2631 (1976).

    CAS  Google Scholar 

  23. K. Nozawa and S. Nakajima, J. Nat. Prod., 42(4), 374 – 377 (1979).

    CAS  Google Scholar 

  24. M. Alajarin, P. Molina, and A. Vidal, J. Nat. Prod., 60(7), 747 – 748 (1997).

    CAS  Google Scholar 

  25. J.-S. Kim, K. Shinya, K. Furihata, et al., Tetrahedron Lett., 38(19), 3431 – 3434 (1997).

    CAS  Google Scholar 

  26. A. Badre, A. Boulanger, E. Abou-Mansour, et al., J. Nat. Prod., 57(4), 528 – 533 (1994).

    PubMed  CAS  Google Scholar 

  27. C. Moquin and M. Guyot, Tetrahedron Lett., 25(44), 5047 – 5048 (1984).

    CAS  Google Scholar 

  28. J.-Y. Charcosset, J.-P. Bendirdjian, M.-F. Lantieri, et al., Cancer Res., 45(12), 4229 – 4236 (1985).

    PubMed  CAS  Google Scholar 

  29. S. A. Abas, M. B. Hossain, D. Helm, et al., J. Org. Chem., 61(8), 2709 – 2712 (1996).

    PubMed  CAS  Google Scholar 

  30. Y. Konda, M. Onda, A. Hirano, et al., Chem. Pharm. Bull., 28(10), 2987 – 2993 (1980).

    CAS  Google Scholar 

  31. K. Kawai, K. Nozawa, S. Nakajima, et al., Chem. Pharm. Bull., 32(1), 94 – 98 (1984).

    CAS  Google Scholar 

  32. B. K. S. Yeung, Y. Nakao, R. B. Kinnel, et al., J. Org. Chem., 61, No. 20, 7168 – 7173 (1996).

    PubMed  CAS  Google Scholar 

  33. Y. Nakao, B. K. S. Yeung, W. Y. Yoshida, et al., J. Am. Chem. Soc., 117(31), 8271 – 8272 (1995).

    CAS  Google Scholar 

  34. S. M. Verbitski, C. L. Mayne, and R. A. Davis, J. Org. Chem., 67(20), 7124 – 7126 (2002).

    PubMed  CAS  Google Scholar 

  35. A. Numata, C. Takahashi, Y. Ito, et al., Tetrahedron Lett., 34, No. 14, 2355 – 2358 (1993).

    CAS  Google Scholar 

  36. R. G. S. Berlinck, R. Britton, E.Piers, et al., J. Org. Chem., 63(26), 9850 – 9856 (1998).

    CAS  Google Scholar 

  37. A. S. Ratnayake, W. Y. Yoshida, S. L. Mooberry, et al., J. Org. Chem., 66(26), 8717 (2001).

    PubMed  CAS  Google Scholar 

  38. A. S. Ratnayake, W. Y. Yoshida, S. L. Mooberry, et al., J. Org. Chem., 68(10), 1640 (2003).

    CAS  Google Scholar 

  39. H. C. Vervoort, W. Fenical, and P. A. Keifer, J. Nat. Prod., 62(2), 389 – 391 (1999).

    PubMed  CAS  Google Scholar 

  40. R. Jadulco, R. A. Edrada, R.Ebel, et al., J. Nat. Prod., 67(1), 78 – 81 (2004).

    PubMed  CAS  Google Scholar 

  41. P. W. Dalsgaard, J. W. Blunt, M. H. G. Munro, et al., J. Nat. Prod., 68(2), 258 – 261 (2005).

    PubMed  CAS  Google Scholar 

  42. E. Piers, R. Britton, and R. J. Andersen, J. Org. Chem., 65(22), 530 – 535 (2000).

    PubMed  CAS  Google Scholar 

  43. JP Pat. No. 10130269; http://ep.espacenet.com.

  44. R. Vleggaar and P. L. Wessels, J. Chem. Soc., Chem. Commun., No. 4, 160 – 162 (1980).

  45. WO Pat. No. 9705137; http://ep.espacenet.com.

  46. DE Pat. No. 4308788; http://ep.espacenet.com.

  47. SI Pat. No. 705831; http://ep.espacenet.com.

  48. US Pat. No. 5,783,575; http://ep.espacenet.com

  49. DE Pat. No. 19615119; http://ep.espacenet.com

  50. EP Pat. 0799829; http://ep.espacenet.com

  51. FR Pat. No. 2846329; http://ep.espacenet.com

  52. FR Pat. No. 2846330; http://ep.espacenet.com

  53. V. G. Granik, Organic Chemistry [in Russian], Vyzovskaya Kniga, Moscow (2003).

    Google Scholar 

  54. N. Barbulescu, C. Bornaz, and C. Greff, Rev. Chim. (Bucharest, Rom.), 22(5), 269 – 270 (1971).

    CAS  Google Scholar 

  55. V. Boekelheide and C. Ainsworth, J. Am. Chem. Soc., 72, 2132 – 2134 (1950).

    CAS  Google Scholar 

  56. N. F. Kucherova and N. K. Kochetkov, Zh. Org. Khim., 26(11), 3149 – 3154 (1956).

    CAS  Google Scholar 

  57. A. Ebnother, P. Niklaus, and R. Suess, Helv. Chim. Acta, 52(3), 629 – 638 (1969).

    Google Scholar 

  58. J. Moron, C. Landras, and E. Bisagni, J. Heterocycl. Chem., 29, 1573 – 1576 (1992).

    CAS  Google Scholar 

  59. E. N. Novikova, I. D. Silenko, N. F. Kucherova, et al., Khim. Geterotsikl. Soedin., No. 8, 1070 – 1073 (1971).

  60. N. K. Kochetkov, N. F. Kucherova, L. P. Pronina, et al., Zh. Org. Khim., 29(11), 3620 – 3625 (1959).

    CAS  Google Scholar 

  61. N. P. Buu-Hoi, O. Roussel, and P. Jacquignon, J. Chem. Soc., 708 – 710 (1964).

  62. A. C. Harbert, J. J. Plattner, and W. M. Welch, J. Med. Chem., 23(6), 635 – 643 (1980).

    PubMed  CAS  Google Scholar 

  63. W. M. Welch, Synthesis, No. 9, 645 – 646 (1977).

  64. E. Bisagni, C. H. Nguyen, A. Pierr, et al., J. Med. Chem., 31(2), 398 – 405 (1988).

    PubMed  CAS  Google Scholar 

  65. C. H. Nguyen and E. Bisagni, Tetrahedron, 43(3), 527 – 535 (1987).

    Google Scholar 

  66. C. Ducroeq, A. Civier, J. Andre-Louisfert, et al., J. Heterocycl. Chem., 12(5), 963 – 967 (1975).

    Google Scholar 

  67. F. G. Mann, A. F. Prior, and T. J. Wilcox, J. Chem. Soc., 3830 – 3834 (1959).

  68. A. Settimo, G. Primofiore, G. Biagi, et al., Farmaco – Ed. Sci., 31(8), 587 – 595 (1976).

    Google Scholar 

  69. A. Settimo, G. Biagi, G. Primofiore, et al., Farmaco – Ed. Sci., 33(10), 770 – 780 (1978).

    Google Scholar 

  70. C. H. Nguyen, J. M. Lhoste, F. Lavelle, et al., J. Med. Chem., 33(5), 1519 – 1528 (1990).

    PubMed  CAS  Google Scholar 

  71. P. Helissey, H. Parrot-Lopez, J. Renault, and S. Cros, Eur. J. Med. Chem., 22, 366 – 368 (1987).

    CAS  Google Scholar 

  72. E.-S. Ibrahim, A. M. Montomerie, A. H. Sneddon, et al., Eur. J. Med. Chem., 23, 183 – 188 (1988).

    CAS  Google Scholar 

  73. M. L. Go, H. L. Koh, T. L. Ngiam, et al., Eur. J. Med. Chem., 27, 391 – 394 (1992).

    CAS  Google Scholar 

  74. L. M. Webel, S. J.Kesten, and W. R. Turner, Eur. J. Med. Chem., 28, 837 – 852 (1993).

    Google Scholar 

  75. L. He, H.-X. Chang, T.-C. Chou, et al., Eur. J. Med. Chem., 38, 101 – 107 (2003).

    PubMed  CAS  Google Scholar 

  76. C. H. Nguyen, C. Marchand, S. Delage, et al., J. Am. Chem. Soc., 120, 2501 – 2507 (1998).

    CAS  Google Scholar 

  77. P. Helissey, H. Parrot-Lopez, J. Renault, et al., Chem. Pharm. Bull., 35, No. 9, 3547 – 3557 (1987).

    PubMed  CAS  Google Scholar 

  78. P. Helissey, S. Giorgi-Renault, J. Renault, et al., Chem. Pharm. Bull., 37(3), 675 – 679 (1989).

    PubMed  CAS  Google Scholar 

  79. J. T. Braunroltz and F. G. Mann, J. Chem. Soc., 381 – 392 (1955).

  80. R. A. Abramovith and K. A. H. Adams, Can. J. Chem., 40(5), 864 – 869 (1962).

    Google Scholar 

  81. S. Okuda and M. M. Robison, J. Am. Chem. Soc., 81(3), 740 – 743 (1959).

    CAS  Google Scholar 

  82. A. H. Kelly and J. Parrick, Can. J. Chem., 44(21), 2455 – 2459 (1966).

    CAS  Google Scholar 

  83. T. Yamazaki, K. Matoba, S. Imoto, et al., Chem. Pharm. Bull., 24(12), 3011 – 3018 (1976).

    CAS  Google Scholar 

  84. Yu. M. Yutilov, N. N. Smolyar, and A. S. Volchkov, Khim.-farm. Zh., 34(12), 33 – 34 (2000).

    Google Scholar 

  85. O. Bremer, Ann., 514, 279 – 291 (1934).

    CAS  Google Scholar 

  86. A. Molina, J. J. Vaquero, J. L. Garcia-Navio, et al., Tetrahedron, 34(16), 2673 – 2676 (1993).

    CAS  Google Scholar 

  87. L. K. Mehta, J. Parrick, and F. Payne, J. Chem. Soc., Perkin Trans 1, No. 11, 1261 – 1267 (1993).

  88. R. Robinson and S. Thornley, J. Chem. Soc., 125, 2169 – 2176 (1924).

    CAS  Google Scholar 

  89. P. Nantka-Namirski, Acta Pol. Pharm., 18, 449 – 460 (1961); Chem. Abstr., 58(4), 3424 (1963).

    Google Scholar 

  90. P. Nantka-Namirski, Acta Pol. Pharm., 18, 391 – 399 (1961); Chem. Abstr., 57(13), 16554 (1962).

    Google Scholar 

  91. P. Nantka-Namirski, Acta Pol. Pharm., 19, No. 3, 229 – 242 (1962); Chem. Abstr., 59(13), 15260 (1963).

  92. M. S. Allen, Y.-C. Tan, M. L. Trudell, et al., J. Med. Chem., 33(5), 2343 – 2357 (1990).

    PubMed  CAS  Google Scholar 

  93. H. Akimoto, A. Kawai, and H. Nomura, Bull. Chem. Soc. Jpn., 58, 123 – 130 (1985).

    CAS  Google Scholar 

  94. H. Akimoto, A. Kawai, and H. Nomura, Chem. Lett., 1061 – 1064 (1977).

  95. P. Nantka-Namirski, Acta Pol. Pharm., 34(5), 455 – 458 (1977); Chem. Abstr., 88, 190633 (1978).

    Google Scholar 

  96. A. Molina, J. J. Vaquero, J. L. Garcia-Navio, et al., J. Org. Chem., 61(16), 5587 – 5599 (1996).

    CAS  Google Scholar 

  97. T. Kosuge, K. Tsuji, K. Wakabayashi, et al., Chem. Pharm. Bull., 26(2), 611 – 619 (1978).

    PubMed  CAS  Google Scholar 

  98. Food Safety, Marcel Dekker, New York (1995), pp. 336 – 338.

  99. E. B. Brittebo, Carcinogenesis, 15(4), 667 – 672 (1994).

    PubMed  CAS  Google Scholar 

  100. T. Toyodaa, R. K. B. Brobeyb, G. Sanob, et al., Biochem. Biophys. Res. Commun., 235(3), 515 – 519 (1997).

    Google Scholar 

  101. A. Beauchard, H. Chabane, S. Sinbandhit, et al., Tetrahedron, 62(8), 1895 – 1903 (2006).

    CAS  Google Scholar 

  102. C. Rivalle, C. Ducroeq, and E. Bisagni, J. Chem. Soc., Perkin Trans. 1, 138 – 140 (1979).

  103. E. Spath and K. Eiter, Chem. Ber., 73(6), 719 – 729 (1940).

    Google Scholar 

  104. K. Eiter and A. Nezval, Monatsh. Chem., 81(3), 404 – 413 (1950).

    CAS  Google Scholar 

  105. W. Lawson, W. H. Perkin, and R. Robinson, J. Chem. Soc., 125, 626 – 657 (1924).

    CAS  Google Scholar 

  106. R. Robinson and S. Thornley, J. Chem. Soc., 125, 2169 – 2176 (1924).

    CAS  Google Scholar 

  107. P. A. S. Smith and J. H. Boyer, J. Am. Chem. Soc., 73, 2626 – 2629 (1951).

    CAS  Google Scholar 

  108. P. M. Fresneda, P. Molina, and S. Delgado, Tetrahedron Lett., 40, 7275 – 7278 (1999).

    CAS  Google Scholar 

  109. G. W. Gribble, J. Chem. Soc., Perkin Trans. 1, 1045 – 1074 (2000).

  110. G. Timari, T. Soos, and G. Haos, Synlett, 9, 1067 – 1068 (1997).

    Google Scholar 

  111. J. Schofield, R. K. Smalley, D. I. C. Scopes, and D. I. Patel, J. Chem. Res. (S), No. 5, 164 – 165 (1987).

  112. J.-L. Pousset, M.-T. Martin, A. Jossang, et al., Phytochemistry, 39(3), 735 – 738 (1995).

    CAS  Google Scholar 

  113. M. H. M. Sharaf, P. L. Schiff, A. N. Tackie, et al., J. Heterocycl. Chem., 33(2), 239 – 243 (1996).

    CAS  Google Scholar 

  114. S. V. Dubovitskii, O. S. Radchenko, and V. L. Novikov, Izv. Akad. Nauk, Ser. Khim., No. 11, 2797 – 2798 (1996).

  115. R. N. Kumar, T. Suresh, and P. S. Mohan, Tetrahedron Lett., 43(18), 3327 – 3328 (2002).

    CAS  Google Scholar 

  116. T. H. M. Jonckers, B. U. W. Maes, G. L. F. Lemiere, et al., Synlett, 5, 615 – 618 (2003).

    Google Scholar 

  117. P. Molina, M. Alajarin, and A. Vidal, Tetrahedron, 46(3), 1063 – 1078 (1990).

    CAS  Google Scholar 

  118. S. Cacchi, G. Fabrizi, P. Pace, et al., Synlett, 5, 620 – 622 (1999).

    Google Scholar 

  119. A. Mouaddib, B. Joseph, A. Hasnaoui, et al., Synthesis, No. 4, 549 – 556 (2000).

  120. J. Bergman, R. Engqvist, C. Stalhandske, et al., Tetrahedron, 59, 1033 – 1048 (2003).

    CAS  Google Scholar 

  121. H. Li, H. Yang, J. L. Petersen, et al., J. Org. Chem., 69(13), 4500 – 4508 (2004).

    PubMed  CAS  Google Scholar 

  122. R. A. Abramovith and K. A. H. Adams, Can. J. Chem., 39(12), 2516 – 2528 (1961).

    Google Scholar 

  123. R. A. Abramovith, K. A. H. Adams, and A. D. Notation, Can. J. Chem., 38(11), 2152 – 2160 (1960).

    Google Scholar 

  124. R. A. Abramovith and J. Kalinowski, J. Heterocycl. Chem., 11(6), 857 – 861 (1974).

    Google Scholar 

  125. R. A. Abramovith, Can. J. Chem., 39(11), 2273 – 2276 (1961).

    Google Scholar 

  126. V. M. Clark, A. Cox, and E. J. Herbert, J. Chem. Soc. (Org.), 831 (1968).

  127. J. Bratt and H. Suschitzky, J. Chem. Soc., Chem. Commun., 949 – 950 (1972).

  128. J. Bratt, B. Iddon, A. Mack, et al., J. Chem. Soc., Perkin Trans. 1, 648 – 656 (1980).

  129. E. P. Fokin, T. N. Gerasimova, T. V. Fomenko, et al., Zh. Org. Khim., 14, 834 – 841 (1978).

    CAS  Google Scholar 

  130. T. Iwaki, A. Yasuhara, and T. Sakamoto, J. Chem. Soc., Perkin Trans. 1, 1505 – 1510 (1999).

  131. C. Chen, D. R. Lieberman, R. D. Larsen, et al., J. Org. Chem., 62(9), 2677 – 2679 (1997).

    Google Scholar 

  132. P. Rocca, F. Marsais, A. Godard, and G. Queguiner, Tetrahedron, 49(1), 49 – 64 (1993).

    CAS  Google Scholar 

  133. P. Rocca, C. Cochennec, F. Marsais, et al., J. Org. Chem., 58(27), 7832 – 7838 (1993).

    CAS  Google Scholar 

  134. E. Arzel, P. Rocca, F. Marsais, et al., J. Heterocycl. Chem., 34(4), 1205 – 1210 (1997).

    CAS  Google Scholar 

  135. E. Arzel, P. Rocca, F. Marsais, et al., Heterocycles, 50(1), 215 – 226 (1999).

    CAS  Google Scholar 

  136. E. Arzel, P. Rocca, P. Grellier, et al., J. Med. Chem., 44(6), 949 – 960 (2001).

    PubMed  CAS  Google Scholar 

  137. C. Papamicael, G. Dupas, J. Bourguignon, et al., Tetrahedron Lett., 35(24), 4099 – 4102 (1994).

    CAS  Google Scholar 

  138. C. Papamicael, G. Dupas, G. Queguiner, et al., Heterocycles, 47(2), 991 – 1004 (1998).

    CAS  Google Scholar 

  139. F. Mongin and G. Queguiner, Tetrahedron, 57(19), 4059 – 4090 (2001).

    CAS  Google Scholar 

  140. T. A. Enaler and J. Wanner, Tetrahedron Lett., 38(35), 6135 – 6138 (1997).

    Google Scholar 

  141. T. A. Enaler and J. Wanner, J. Org. Chem., 65(8), 2444 – 2457 (2000).

    Google Scholar 

  142. P. J. Bunyan and J. I. G. Cadogan, J. Chem. Soc., 42 – 49 (1963).

  143. N. Moskalev, M. Barbasiewicz, and M. Makosza, Tetrahedron, 60(2), 347 – 358 (2004).

    CAS  Google Scholar 

  144. H. Suschitzky, B. J. Wakefield, K. Walocha, et al., J. Chem. Soc., Perkin Trans. 1, No. 3, 637 – 641 (1983).

  145. S. Hibino, E. Sugino, Y. Shintani, et al., Heterocycles, 30(1), 271 – 273 (1990).

    CAS  Google Scholar 

  146. S. Hibino, J. Org. Chem., 49(25), 5006 – 5008 (1984).

    CAS  Google Scholar 

  147. S. Hibino, E. Sugino, T. Kuwada, et al., J. Org. Chem., 57(22), 5917 – 5921 (1992).

    CAS  Google Scholar 

  148. S. A. Snyder, D. A. Vosburg, and M. G. Jarvis, Tetrahedron, 56(30), 5329 – 5336 (2000).

    CAS  Google Scholar 

  149. J. H. Markgraf, S. A. Snyder, and D. A. Vosburg, Tetrahedron Lett., 39(10), 1111 – 1112 (1998).

    CAS  Google Scholar 

  150. T. L. Gilchrist, P. D. Kemmitt, and A. L. Germain, Tetrahedron, 53(12), 4447 – 4456 (1997).

    CAS  Google Scholar 

  151. E. Malamidou-Xenikaki, X. N. Stampelos, T. A. Charalambis, et al., Tetrahedron, 53(2), 747 – 758 (1997).

    CAS  Google Scholar 

  152. G. K. Biswas, A. C. Nath, B. Mukherjee, et al., Tetrahedron Lett., 33(1), 117 – 118 (1992).

    CAS  Google Scholar 

  153. T. Janosik and J. Beraman, Tetrahedron, 55(8), 2371 – 2380 (1999).

    CAS  Google Scholar 

  154. L. K. Dalton, S. Demerac, and T. Teitei, Aust. J. Chem., 22, 185 – 195 (1969).

    CAS  Google Scholar 

  155. E. S. Krichevskii, L. M. Alekseeva, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 1, 1483 – 1486 (1990).

  156. G. Dupas, J. Dufols, and G. Queguiner, J. Heterocycl. Chem., 20, 967 – 970 (1983).

    CAS  Google Scholar 

  157. C. Papamicael, G. Dupas, G. Queguiner, et al., Heterocycles, 49(1), 361 – 373 (1998).

    CAS  Google Scholar 

  158. K. Takeda, K. Shudo, T. Okamoto, et al., Chem. Pharm. Bull., 29(5), 1280 – 1285 (1991).

    Google Scholar 

  159. T. Sakamoto, A. Numata, H. Saiton, and Y. Kondo, Chem. Pharm. Bull., 47(12), 1740 – 1743 (1999).

    CAS  Google Scholar 

  160. M. Somei, F. Yamada, and G. Yamamura, Chem. Pharm. Bull., 46(2), 191 – 198 (1998).

    CAS  Google Scholar 

  161. S. K. Singh, M. Dekhane, M. Hyaric, et al., Heterocycles, 44(1), 379 – 391 (1997).

    CAS  Google Scholar 

  162. M. Somie, M. Nakajou, T. Teramoto, et al., Heterocycles, 51(8), 1949 – 1956 (1999).

    Google Scholar 

  163. G. L. Karrik and N. P. Peet, J. Heterocycl. Chem., 23(4), 1055 – 1057 (1986).

    Google Scholar 

  164. F. A. Trofimov, V. I. Ryabchenko, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 10, 1343 – 1346 (1975).

  165. E. J. Reist, W. W. Bradford, G. R. Gordon, et al., J. Labelled Cmpds. Radiopharm., 21(3), 223 – 227 (1984).

    CAS  Google Scholar 

  166. T. V. Golovko, N. P. Solov?eva, O. S. Anisimova, et al., Izv. Akad. Nauk, Ser. Khim., No. 1, 171 – 179 (2008).

  167. O. B. Smirnova, T. V. Golovko, L. M. Alekseeva, et al., Izv. Akad. Nauk, Ser. Khim., No. 11, 2361 – 2368 (2008).

  168. O. B. Smirnova, T. V. Golovko, L. M. Alekseeva, et al., Izv. Akad. Nauk, Ser. Khim., No. 1, 174 – 181 (2010).

  169. O. B. Smirnova, Candidate Dissertation in Chemical Sciences, Moscow (2010).

  170. S. Yu. Ryabova, L. M. Alekseeva, and V. G. Granik, Khim.-farm. Zh., 30(9), 29 – 34 (1996).

    CAS  Google Scholar 

  171. S. Yu. Ryabova, L. M. Alekseeva, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 3, 362 – 367 (2000).

  172. S. Yu. Ryabova, L. M. Alekseeva, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 8, 1086 – 1094 (2001).

  173. N. A. Lantsetti, S. Yu. Ryabova, L. M. Alekseeva, et al., Izv. Akad. Nauk, Ser. Khim., No. 3, 470 – 475 (2002).

  174. C. Papamicael, G. Queguiner, J. Bourguignon, and G. Dupas, Tetrahedron, 57(25), 5385 – 5391 (2001).

    CAS  Google Scholar 

  175. I. S. Yaroslavskii, V. S. Velezheva, and N. N. Suvorov, Zh. Org. Khim., 21(2), 432 – 436 (1985).

    CAS  Google Scholar 

  176. E. Erba, M. L. Gelmi, and D. Pocar, Tetrahedron, 56(51), 9991 – 9997 (2000).

    CAS  Google Scholar 

  177. T. V. Golovko, N. P. Solov’eva, and V. G. Granik, Khim.-farm. Zh., 30(10), 32 – 36 (1996).

    CAS  Google Scholar 

  178. T. V. Golovko, N. P. Solov?eva, G. A. Bogdanova, et al., Khim. Geterotsikl. Soedin., No. 9, 1190 – 1198 (1991).

  179. T. V. Golovko, N. P. Solov’eva, and V. G. Granik, Khim.-farm. Zh., 28(5), 48 – 50 (1994).

    CAS  Google Scholar 

  180. H. Zhang and R. C. Larock, Org. Lett., 3(20), 3083 – 3086 (2001).

    PubMed  CAS  Google Scholar 

  181. H. Zhang and R. C. Larock, Org. Lett., 4(18), 3035 – 3038 (2002).

    PubMed  CAS  Google Scholar 

  182. H. Zhang and R. C. Larock, Tetrahedron Lett., 43(8), 1359 – 1362 (2002).

    CAS  Google Scholar 

  183. H. Zhang and R. C. Larock, J. Org. Chem., 67(26), 9318 – 9330 (2002).

    PubMed  CAS  Google Scholar 

  184. H. Zhang and R. C. Larock, J. Org. Chem., 67(20), 7048 – 7056 (2002).

    PubMed  CAS  Google Scholar 

  185. H. Zhang and R. C. Larock, J. Org. Chem., 68(13), 5132 – 5138 (2003).

    PubMed  CAS  Google Scholar 

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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 44, No. 12, pp. 6 – 30, December, 2010.

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Smirnova, O.B., Golovko, T.V. & Granik, V.G. Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review). Pharm Chem J 44, 654–678 (2011). https://doi.org/10.1007/s11094-011-0540-z

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