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Synthesis of alkylindoles (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods for obtaining alkylindoles, excluding the Fischer synthesis and direct alkylation, developed during the last 15 years are correlated.

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Literature Cited

  1. R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York (1970).

    Google Scholar 

  2. R. K. Brown, in: Indoles, edited by W. J. Houlihan, Wiley Interscience, New York (1972).

    Google Scholar 

  3. B. Robinson, Chem. Rev., 69, 227 (1969).

    Google Scholar 

  4. M. G. Reineke, J. F. Sebastian, H. W. Johnson, and G. Pyun, J. Org. Chem., 37, 3066 (1972).

    Google Scholar 

  5. N. N. Suvorov, Yu. I. Smushkevich, V. S. Velezheva, and V. S. Rozhkov, Khim. Geterotsikl. Soedin., 2, 191 (1976).

    Google Scholar 

  6. W. Weber and H. Hockel, Interphase Catalysis in Organic Synthesis [Russian translation], Mir, Moscow (1980), p. 234.

    Google Scholar 

  7. I. I. Grandberg, Izv. Timiryazev. Sel'skokhoz. Akad., 5, 188 (1972).

    Google Scholar 

  8. V. A. Zagorevskii, N. F. Kucherova, N. M. Sharkova, T. I. Ivanova, and S. M. Klyuev, Khim. Geterotsikl. Soedin., 10, 1353 (1975).

    Google Scholar 

  9. Yu. B. Vysotskii, N. M. Przheval'skii, B. P. Zenskii, I. I. Grandberg, and L. Yu. Kostromina, Khim. Geterotsikl. Soedin., No. 7, 898 (1986).

    Google Scholar 

  10. C. Baccolini and P. E. Todeseo, J. Chem. Soc., Perkin Trans. 1, 3, 535 (1983).

    Google Scholar 

  11. V. Dave, Org. Prep. Proced., 8, 41 (1976).

    Google Scholar 

  12. N. N. Suvorov, N. E. Starostenko, T. V. Antipina, V. Ya. Kanterov, N. Ya. Podkalyuzina, and O. V. Bulgakov, Zh. Fiz. Khim., 46, 2028 (1972).

    Google Scholar 

  13. V. Ya. Kanterov, N. N. Suvorov, N. E. Starostenko, and Yu. P. Oleinikov, Zh. Fiz. Khim., 44, 1583 (1970).

    Google Scholar 

  14. H. Hayashi, K. Kurokawa, W. Hosokawa, T. Tanaka, and T. Okazaki, J. Catal., 66, 49 (1980).

    Google Scholar 

  15. R. Fusco and P. Sannikolo, Khim. Geterotsikl. Soedin., No. 2, 200 (1978).

    Google Scholar 

  16. R. B. Carlin and M. S. Moores, J. Am. Chem. Soc., 84, 4107 (1962).

    Google Scholar 

  17. J. Fujiwara, Y. Fukutani, H. Sano, K. Naruoka, and H. Yamamoto, J. Am. Chem. Soc., 105, 7177 (1983).

    Google Scholar 

  18. H. Plieninger and H. Sirowey, Chem. Ber., 104, 2027 (1971).

    Google Scholar 

  19. A. K. Sinhababu and R. T. Borchardt, J. Org. Chem., 48, 3347 (1983).

    Google Scholar 

  20. W. C. Oijksman, W. Verboom, D. N. Reinhoudt, C. G. Hale, S. Harkema, and G. J. van Hummel, Tetrahedron Lett., 25, 2052 (1984).

    Google Scholar 

  21. P. A. S. Smith, C. D. Rowe, and D. W. Hansen, Jr., Tetrahedron Lett., 24, 5169 (1983).

    Google Scholar 

  22. H. Suschitzky and Z. Wiss, Karl Marx Univ., Leipzig, Math. Naturwiss. 32, 416 (1983); Ref. Zh. Khim., 5Zh292 (1984).

    Google Scholar 

  23. M. Mori, K. Chiba, and Y. Ban, Tetrahedron Lett., No. 14, 1037 (1977).

    Google Scholar 

  24. L. S. Hegedus, G. F. Allen, J. J. Bozell, and E. L. Waterman, J. Am. Chem. Soc., 100, 5800 (1978).

    Google Scholar 

  25. L. S. Hegedus, G. F. Allen, and D. J. Olsen, J. Am. Chem. Soc., 102, 3583 (1980).

    Google Scholar 

  26. S. Jolidon and H.-J. Hansen, Helv. Chim. Acta, 62, 2581 (1979).

    Google Scholar 

  27. S. J. Tremost and Ur Rahman Hayat, J. Am. Chem. Soc., 106, 5759 (1984).

    Google Scholar 

  28. K. Krowicki, N. Paillous, M. Riviere, and A. Lattes, J. Heterocycl. Chem., 13, 555 (1976).

    Google Scholar 

  29. A. Tungler, T. Mathe, J. Petro, and Z. Bende, Hungarian Patent No. 21507; Chem. Abstr., 97, 109833 (1982).

    Google Scholar 

  30. R. Beugelmans and G. Roussi, J. Chem. Soc., Chem. Commun., No. 21, 950 (1979).

    Google Scholar 

  31. R. R. Bard and J. E. Bunnett, J. Org. Chem., 45, 1547 (1980).

    Google Scholar 

  32. R. Beugelmans and G. Roussi, Tetrahedron, 37, 393 (1981).

    Google Scholar 

  33. J. E. Bunnett, Acc. Chem. Res., 11, 1 (1978).

    Google Scholar 

  34. J. Suzuki, S. V. Thiruvikraman, and A. Osuca, Synthesis, 7, 616 (1984).

    Google Scholar 

  35. K. Boujlel, J. Simonet, G. Roussi, and R. Beugelmans, Tetrahedron Lett., 23, 1736 (1982).

    Google Scholar 

  36. S. Blechert, Tetrahedron Lett., 25, 1547 (1984).

    Google Scholar 

  37. S. Blechert, Helv. Chim. Acta, 68, 1835 (1985).

    Google Scholar 

  38. P. Martin, Helv. Chim. Acta, 67, 1647 (1984).

    Google Scholar 

  39. P. Martin, British Patent No. 2114563; Chem. Abstr., 100, 6336 (1984).

    Google Scholar 

  40. S. J. Danishefsky and G. B. Phillips, Tetrahedron Lett., 25, 3159 (1984).

    Google Scholar 

  41. K. Mohri, Y. Oikawa, K. Hirao, and O. Yonemitsu, Heterocycles, 19, 515 (1982).

    Google Scholar 

  42. M. F. Carroll, J. Chem. Soc., No. 6, 704 (1940).

    Google Scholar 

  43. W. Hoffmann, H. Paseduch, H. Pommer, and W. Reif, Annalen, 747, 60 (1971).

    Google Scholar 

  44. P. G. Garsmann, T. J. van Bergen, and D. P. Gilbert, J. Am. Chem. Soc., 96, 5495 (1974).

    Google Scholar 

  45. D. B. Dean and W. E. Truce, J. Org. Chem., 46, 3575 (1981).

    Google Scholar 

  46. S. Raucher and G. A. Koolpe, J. Org. Chem., 48, 2066 (1983).

    Google Scholar 

  47. E. Ucciani and A. Bonfand, J. Chem. Soc., Chem. Commun., No. 3, 82 (1981).

    Google Scholar 

  48. L. I. Krause, Heterocycles, 16, 1119 (1981).

    Google Scholar 

  49. R. D. Clark and D. B. Repke, Heterocycles, 22, 195 (1984).

    Google Scholar 

  50. A. D. Batcho and W. Leimgruber, Offen. 2057840 (Germ); Chem. Abstr., 75, 63605 (1971).

    Google Scholar 

  51. M. Somei, F. Yamada, and C. Kameko, Heterocycles, 14, 101 (1980).

    Google Scholar 

  52. T. Sugasawa, M. Adachi, K. Saskura, and A. Kitagawa, J. Org. Chem., 44, 578 (1979).

    Google Scholar 

  53. T. Sugasawa, M. Adachi, and A. Kawasaki, Canadian Patent No. 1127163; Chem. Abstr., 97, 215995 (1982).

    Google Scholar 

  54. P. Bravo, G. Gaudiano, and A. Umari, Gazz. Chim. Ital., 100, 652 (1970).

    Google Scholar 

  55. J. E. Norlander, D. B. Catalone, K. D. Kotian, and R. M. Stevens, and J. E. Haky, J. Org. Chem., 46, 778 (1971).

    Google Scholar 

  56. M. Mori and Y. Ban, Tetrahedron Lett., No. 21, 1803 (1976).

    Google Scholar 

  57. J. C. Rodriguez and L. Canoira, J. Heterocycl. Chem., 22, 883 (1985).

    Google Scholar 

  58. R. Odle, B. Blevins, M. Ratcliff, and L. S. Hegedus, J. Org. Chem., 45, 2709 (1980).

    Google Scholar 

  59. M. M. Mauri, P. A. Moggi, and U. Romanov, French Patent No. 21338; Ref. Zh. Khim., 14N, 242 (1973).

  60. S. Esteban, J. M. Martinas, M. P. Martinez-Alcazar, M. Martinez, and A. R. Agarrabeitia, Bull. Soc. Chim. Belges, 92, 715 (1983).

    Google Scholar 

  61. Mitsui Toatsu Chemicals, Inc., Japanese Patent No. 81186154; Chem. Abstr., 96, 35077 (1982).

    Google Scholar 

  62. Mitsui Toatsu Chemicals, Inc., Japanese Patent No. 81169668; Chem. Abstr. 96, 162539 (1982).

    Google Scholar 

  63. Mitsui Toatsu Chemicals, Inc., Japanese PatentNo. 81110672; Chem. Abstr., 96, 19966 (1982).

    Google Scholar 

  64. F. Matsuda, T. Kato, and T. Kiyoura, Canadian Patent No. 1150729; Chem. Abstr., 100, 6336 (1984).

    Google Scholar 

  65. F. Matsuda and T. Kato, Canadian Patent No. 114396; Chem. Abstr., 100, 6334 (1984).

    Google Scholar 

  66. T. Honda and K. Terada, Japanese Patent Application No. 58-29762; Ref. Zh. Khim., 100, 199 (1984).

  67. F. Pozzi and M. R. Langella, Gazz. Chim. Ital., 93, 1392 (1963).

    Google Scholar 

  68. K. C. Bass and P. Nababsing, Org. Prep. Proced., 2, 221 (1970).

    Google Scholar 

  69. W. J. Houlihan, V. A. Parrino, and Y. Uike, J. Org. Chem., 46, 4511 (1981).

    Google Scholar 

  70. R. E. Ludt, J. S. Griffits, K. N. McGrathi, and C. R. Hauser, J. Org. Chem., 38, 1668 (1973).

    Google Scholar 

  71. W. J. Houlihan, US Patent No. 3987059; Chem. Abstr., 86, 43558 (1977).

    Google Scholar 

  72. Y. Ito, K. Kobayashi, and T. Saegusa, J. Am. Chem. Soc., 99, 3532 (1977).

    Google Scholar 

  73. Y. Ito, K. Kobayashi, N. Seko, and T. Saegusa, Chem. Lett., 10, 1273 (1979).

    Google Scholar 

  74. Y. Ito, K. Kobayashi, N. Seko, and T. Saegusa, Bull. Chem. Soc. Jpn., 54, 73 (1984).

    Google Scholar 

  75. M. Le Corre, A. Hercouet, and H. Le Buron, J. Chem. Soc., Chem Commun., No. 1, 14 (1981).

    Google Scholar 

  76. H. McNab, J. Chem. Soc., Perkin Trans., 3, 377 (1984).

    Google Scholar 

  77. W. N. Speckamp, Heterocycles, 21, 211 (1984).

    Google Scholar 

  78. A. Padwa and P. H. J. Carlsen, Tetrahedron Lett., No. 5, 433 (1978).

    Google Scholar 

  79. J. H. Boyer and G. Mikol, J. Heterocycl. Chem., 9, 1325 (1972).

    Google Scholar 

  80. L. Henn, D. M. B. Hickey, C. J. Moody, and C. W. Reis, J. Chem. Soc., No. 9, 2189 (1984).

    Google Scholar 

  81. H. Hemetsberger, D. Knittel, and H. Weidmann, Monatash., 101, 161 (1970).

    Google Scholar 

  82. C. Wentrup, Adv. Heterocycl. Chem., 28, 231 (1981).

    Google Scholar 

  83. T. L. Gilchrist, C. W. Rees, and J. A. R. Rodrigues, J. Chem. Soc., Chem. Commun., No. 1, 3 (1982).

    Google Scholar 

  84. P. Germeraad and H. W. Moore, J. Org. Chem., 39, 774 (1974).

    Google Scholar 

  85. A. Padwa, J. Smolanoff, and A. Tremper, J. Am. Chem. Soc., 97, 4682 (1975).

    Google Scholar 

  86. A. Padwa, J. Smolanoff, and A. Tremper, J. Org. Chem., 41, 543 (1976).

    Google Scholar 

  87. R. Huisgen and H. König, Chem. Ber., 92, 203 (1959).

    Google Scholar 

  88. R. Huisgen, H. König, and N. Bluker, Chem. Ber., 92, 424 (1959).

    Google Scholar 

  89. T. F. Bunnet and B. F. Hsutfiord, J. Chem. Soc., 83, 1691 (1961).

    Google Scholar 

  90. I. Fleming and M. Woolies, J. Chem. Soc., Perkin Trans. 1, No. 3, 827 (1979).

    Google Scholar 

  91. I. Fleming and M. Woolies, J. Chem. Soc., Perkin Trans. 1, 3, 829 (1979).

    Google Scholar 

  92. P. A. Wender and A. W. White, Tetrahedron Lett., 22, 1475 (1981).

    Google Scholar 

  93. P. A. Wender and A. W. White, Tetrahedron, 39, 3767 (1983).

    Google Scholar 

  94. M. Natsume and H. Muratake, Tetrahedron Lett., No. 36, 3477 (1979).

    Google Scholar 

  95. M. Natsume and H. Muratake, Fukusokan Kagaku Toronkai Koen Yoshishu, No. 12, 96 (1979); Chem. Abstr., 93, 71455 (1980).

    Google Scholar 

  96. M. Natsume and H. Muratake, Heterocycles, 14, 102 (1980).

    Google Scholar 

  97. B. M. Trost, M. Reiffen, and M. Grimmin, J. Am. Chem. Soc., 101, 257 (1979).

    Google Scholar 

  98. S. P. Gromov and Yu. G. Bundel', Dokl. Akad. Nauk SSSR, 281, 585 (1985).

    Google Scholar 

  99. M. A. Yurovskay, V. A. Chertkov, A. Z. Afanas'ev, V. F. Ienkina, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 4, 509 (1985).

    Google Scholar 

  100. M. A. Yurovskaya (Yurowskaya), A. Z. Afanas'ev (Afansyev), V. A. Chertkov, and Yu. G. Bundel' (Bundel), Abstracts of Papers Presented at the 6th International Conference on Organic Synthesis IUPAC, Moscow (1986), p. 124.

  101. M. A. Yurovskaya, M. Bkhaumik, and Yu. G. Bundel', Vest. Moscow State Univ. Ser. Khim., 26, 490 (1985).

    Google Scholar 

  102. M. A. Yurovskaya, A. Z. Afanas'ev, V. A. Chertkov, é. M. Gizatullina, and Yu. G. Bundel', Khim. Geterotsikl. Soedin. (in press).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1155–1172, September, 1987.

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Yurovskaya, M.A. Synthesis of alkylindoles (review). Chem Heterocycl Compd 23, 919–934 (1987). https://doi.org/10.1007/BF00475352

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