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Synthesis of tryptamines by the Fischer method using synthetic precursors and latent forms of amino-butanal (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Information on the synthesis of tryptamines using the Fischer reaction is reviewed. A comparative analysis is made of the methods of production and the reactivity of the various synthetic precursors and latent forms of aminobutanal — the carbonyl component in the synthesis of tryptamines by the Fischer method.

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References

  1. A. J. Ewins and P. P. Laidlaw, Proc. Chem. Soc., 23, 346 (1910).

    Google Scholar 

  2. R. Robinson, The Fischer Indole Synthesis, John Wiley and Sons, New York (1982).

    Google Scholar 

  3. H. M. Hugel and D. J. Kennaway, Org. Prep. Proced, Int., 27, 1 (1995).

    CAS  Google Scholar 

  4. L. Hughes, Org. Prep. Proced. Int., 25, 607 (1993).

    CAS  Google Scholar 

  5. R. J. Sundberg, Indoles, Best Synthetic Methods Series, Academic Press, London (1996).

    Google Scholar 

  6. H. M. Hugel and F. Nurlawis, Heterocycles, 60, 2349 (2003).

    Google Scholar 

  7. G. W. Gribble, J. Chem. Soc., Perkin Trans. 1, 1045 (2000).

  8. E. P. Zakurdaev, E. S. Balenkova, and V. G. Nenajdenko, Izv. Akad. Nauk. Ser. Khim., 1186 (2005).

  9. V. G. Nenajdenko, E. P. Zakurdaev, E. V. Prusov, and E. S. Balenkova, Tetrahedron, 51, 11719 (2004).

    Article  CAS  Google Scholar 

  10. V. G. Nenajdenko, E. P. Zakurdaev, and E. S. Balenkova, Tetrahedron Lett., 43, 8449 (2002).

    Article  CAS  Google Scholar 

  11. I. I. Grandberg and T. I. Zuyanova, Khim. Geterotsikl. Soedin., 875 (1968). [Chem. Heterocycl. Comp., 4, 632 (1968)].

    Google Scholar 

  12. G. I. Zhungietu, V. A. Budylin, and A. N. Kost, Preparative Chemistry of Indole [in Russian], Shtiintsa, Kishinev (1975), p. 66.

    Google Scholar 

  13. I. I. Grandberg, Khim. Geterotsikl. Soedin., 579 (1974). [Chem. Heterocycl. Comp., 10, 501 (1974)].

  14. I. I. Grandberg, Zh. Org. Khim., 19, 2439 (1983).

    CAS  Google Scholar 

  15. L. He, J. L. Li, J. J. Zhang, P. Su, and Sh. L. Zheng, Synth. Commun., 33, 741 (2003).

    Article  CAS  Google Scholar 

  16. B. Pete, I. Bitter, K. Harsanyi, and L. Toke, Heterocycles, 53, 665 (2000).

    CAS  Google Scholar 

  17. C. Groen and C. Christophersen, Acta Chem. Scand., B38, 709 (1984).

    Article  CAS  Google Scholar 

  18. N. N. Suvorov, E. N. Gordeev, and M. V. Vasin, Khim. Geterotsikl. Soedin., 1496 (1974). [Chem. Heterocycl. Comp., 10, 1316 (1974)].

    Google Scholar 

  19. R. A. Abramovitch and D. Shapiro, J. Chem. Soc., 4589 (1956).

  20. R. A. Abramovitch, J. Chem. Soc., 4593 (1956).

  21. G. P. Tokmakov, T. G. Zemlyanova, and I. I. Grandberg, Khim. Geterotsikl. Soedin., 56 (1984). [Chem. Heterocycl. Comp., 20, 47 (1984)].

    Google Scholar 

  22. G. P. Tokmakov and I. I. Grandberg, Khim. Geterotsikl. Soedin., 331 (1980). [Chem. Heterocycl. Comp., 16, 244 (1980)].

    Google Scholar 

  23. G. P. Tokmakov and I. I. Grandberg, USSR Inventor’s Certif. 523096, Byul. Izobr., No. 28 (1976); http://ep.espacenet.com/numberSearch?locale=en_EP

  24. J. Heredia-Moya, Y. Hayakawa, and K. L. Kirk, J. Fluor. Chem., 127, 1256 (2006).

    Article  CAS  Google Scholar 

  25. T. Gungor, P. Malabre, J. M. Teulon, F. Camborde, J. Meignen, F. Hertz, A. V. Oddos, F. Caussade, and A. Cloarec, J. Med. Chem., 37, 4307 (1994).

    Article  CAS  Google Scholar 

  26. T. B. Kline, F. Benington, R. D. Morin, and J. M. Beaton, J. Med. Chem., 25, 908 (1982).

    Article  CAS  Google Scholar 

  27. S. Misztal and J. Boksa, Pol. J. Pharmacol. Pharm., 36, 345 (1984).

    CAS  Google Scholar 

  28. J. I. DeGraw and W. A. Skinner, Can. J. Chem., 45, 63 (1967).

    Article  CAS  Google Scholar 

  29. K. Narayanan and J. M. Cook, J. Org. Chem., 56, 5733 (1991).

    Article  CAS  Google Scholar 

  30. N. N. Suvorov, N. P. Sorokina, and G. N. Tsvetkova, Zh. Obshch. Khim., 34, 1595 (1964).

    CAS  Google Scholar 

  31. S. Terence, S. J. Croker, and R. S. T. Loeffler, Phytochemistry, 25, 683 (1986).

    Article  Google Scholar 

  32. G. W. Gribble, F. L. Switzer, and R. M. Soll, J. Org. Chem., 53, 3164 (1988).

    Article  CAS  Google Scholar 

  33. B. B. Snider and J. B. Neubert, Org. Lett, 7, 2715 (2005).

    Article  CAS  Google Scholar 

  34. H. J. Tappey, Tetrahedron Lett., 31, 1535 (1990).

    Article  Google Scholar 

  35. M. Shimizu, M. Ishikawa, Y. Komoda, and T. Nakajima, Chem. Pharm. Bull, 30, 909 (1982).

    CAS  Google Scholar 

  36. P. J. Parsons, B. Karadogan, and J. A. Macritchie, Synlett, 257 (2001).

  37. A. A. Potekhin, V. V. Sokolov, K. A. Oglobin, and S. M. Isakov, Khim. Geterotsikl. Soedin., 776 (1983). [Chem. Heterocycl. Comp., 19, 622 (1983)].

    Google Scholar 

  38. D. B. Grotjahn and K. P. C. Vollhardt, Synthesis, 579 (1993).

  39. Y. Matsumura, J. Terauchi, T. Yamamoto, T. Konno, and T. Shono, Tetrahedron, 48, 9537 (1992).

    Article  Google Scholar 

  40. T. Shono, Y. Matsumura, K. Uchida, K. Tsubata, and A. Makino, J. Org. Chem., 49, 300 (1984).

    Article  CAS  Google Scholar 

  41. T. Shono, Y. Matsumura, and K. Tsubata, J. Am. Chem. Soc, 103, 1172 (1981).

    Article  CAS  Google Scholar 

  42. M. Mori, Y. Washioka, T. Urayama, K. Yoshiura, K. Chiba, and Y. Ban, J. Org. Chem., 48, 4058 (1983).

    Article  CAS  Google Scholar 

  43. O. P. Goel and R. E. Seamans, Synthesis, 538 (1973).

  44. I. I. Grandberg and N. I. Bobrova, Izv. Timiryazevskoi Sel’skokhoz. Akad., 6, 170 (1970).

    Google Scholar 

  45. D. Starr and R. M. Hixon, Org. Synth., 17, 84 (1937). (Coll. vol. 2, 571 (1943); http://www.orgsyn.org/orgsyn/pdfs/CV2P0571.pdf)

    CAS  Google Scholar 

  46. D. Starr and R. M. Hixon, Syntheses of Organic Products [Russian translation], Coll. 2, Izd. Inostr. Lit., Moscow (1949), p. 450.

    Google Scholar 

  47. K. Weigand and G. Hilgetag, Experimental Methods in Organic Chemistry [Russian translation], Khimiya, Moscow (1968), p. 225; [K. Weigand and G. Hilgetag, Organisch Chemische Experimentierkunst, Johann Ambrosius Barth Verlag, Leipzig (1964)].

    Google Scholar 

  48. D. Starr and R. M. Hixon, J. Am. Chem. Soc, 56, 1595 (1934).

    Article  CAS  Google Scholar 

  49. H. Mohan, D. K. Maity, S. Chattopadhyay, and J. P. Mittal, Chem. Phys. Lett., 300, 493 (1999).

    Article  CAS  Google Scholar 

  50. J. B. Cloke and F. J. Pilgrim, J. Am. Chem. Soc., 61, 2667 (1939).

    Article  CAS  Google Scholar 

  51. R. B. Loftfield, J. Am. Chem. Soc., 73, 1365 (1951).

    Article  CAS  Google Scholar 

  52. W. J. Close, J. Am. Chem. Soc., 79, 1455 (1957).

    Article  CAS  Google Scholar 

  53. A. Taimur, Indian J. Chem., 37B, 1037 (1998); Chem. Abstr., 130, 209423 (1999).

    Google Scholar 

  54. A. J. Mancuso, D. Swern, A. P. Kozikowski, and P. D. Stein, J. Org. Chem., 49, 2305 (1984).

    Google Scholar 

  55. C. E. Masse, A. J. Morgan, and J. S. Panek, Org. Lett., 2, 2571 (2000).

    Article  CAS  Google Scholar 

  56. L. Crombie and D. Fisher, Tetrahedron Lett., 26, 2477 (1985).

    Article  CAS  Google Scholar 

  57. C. Meyer, I. Marek, G. Courtemanche, and J. F. Normant, Tetrahedron, 50, 11665 (1994).

    Article  CAS  Google Scholar 

  58. H. M. Hoffmann and R. Henning, Helv. Chim. Acta, 66, 828 (1983).

    Article  CAS  Google Scholar 

  59. A. Kh. Khusid, Zh. Org. Khim., 23, 1126 (1987).

    Google Scholar 

  60. D. Liu, Q. Guo, and T. Guo, Fine Chemicals (Jingxi Huagong), 17, 130, 158 (2000); Chem. Abstr., 133, 43376 (2000).

    CAS  Google Scholar 

  61. Yu. N. Ogibin, A. Kh. Khusid, and G. I. Nikishin, Izv. Akad. Nauk, Ser. Khim., 941 (1992).

  62. P. L. Anelli, F. Montanari, and S. Quici, Org. Synth., 69, 212 (1990) (Coll. Vol. 8, 367 (1993); http:/www.orgsyn.org/orgsyn/pdfs/CV8P0367.pdf)

    CAS  Google Scholar 

  63. P. L. Anelli, C. Biffi, F. Montanari, and S. Quici, J. Org. Chem., 52, 2559 (1987).

    Article  Google Scholar 

  64. J. W. Williams, E. B. Hershberg, and J. Cason, Org. Synth., 23, 63 (1943) (Coll. Vol. 3, 626 (1955); http:/www.orgsyn.org/orgsyn/pdfs/CV3P0626.pdf)

    CAS  Google Scholar 

  65. D. T. Witiak, K. Tomita, R. J. Patch, and S. J. Enna, J. Med. Chem., 24, 788 (1981).

    Article  CAS  Google Scholar 

  66. J. B. McKay, R. M. Parkhurst, R. M. Silverstein, and W. A. Skinner, Can. J. Chem., 41, 2585 (1963).

    Article  CAS  Google Scholar 

  67. A. Christian and J. Opferm, Brit. Pat. 700825 (1953); http://ep.espacenet.com/numberSearch?locale=en_EP

  68. I. I. Grandberg and N. I. Bobrova, Khim. Geterotsikl. Soedin., 213 (1973). [Chem. Heterocycl. Comp., 9, 196 (1973)].

    Google Scholar 

  69. I. I. Grandberg and N. I. Bobrova, Syntheses of Heterocyclic Compounds [in Russian], Iss. 9, Izd. Akad. Nauk ArmSSR, Erevan (1972), p. 18.

    Google Scholar 

  70. I. I. Grandberg, N. I. Afonina, and T. I. Zuyanova, Khim. Geterotsikl. Soedin., 1038 (1968). [Chem. Heterocycl. Comp., 4, 753 (1968)].

    Google Scholar 

  71. J. E. Audia, J. J. Droste, D. A. Evrard, P. Fludzinski, G. L. Murdoch, and D. L. Nelson, US Pat. 5508284 (1996); http://ep.espacenet.com/numberSearch?locale=en_EP

  72. I. I. Grandberg and N. I. Bobrova, Khim. Geterotsikl. Soedin., 1085 (1974). [Chem. Heterocycl. Comp., 10, 943 (1974)].

    Google Scholar 

  73. I. Fleming and A. Pearce, J. Chem. Soc., Perkin Trans. 1, 251 (1981).

  74. M. G. Pleshakov, A. E. Vasil’ev, I. K. Sarycheva, and N. A. Preobrazhenskii, Zh. Obshch. Khim., 31, 1545 (1961).

    CAS  Google Scholar 

  75. C. P. Forbes, G. L. Wenteler, and A. Wiechers, J. Chem. Soc., Perkin Trans. 1, 2353 (1977).

  76. L. Shouming, K. Seiji, and Y. Shosuke, Tetrahedron, 54, 6661 (1998).

    Article  Google Scholar 

  77. Ch. Chen, C. H. Senanayake, T. J. Bill, R. D. Larsen, T. R. Verhoeven, and P. J. Reider, J. Org. Chem., 59, 3738 (1994).

    Article  CAS  Google Scholar 

  78. A. Van der Gen, K. Wiedhaup, J. Swoboda, J. Harmon, C. Dunathan, and W. S. Johnson, J. Am. Chem. Soc., 95, 2656 (1973).

    Article  Google Scholar 

  79. H. Felkin, Y. Gault, and G. Roussi, Tetrahedron, 26, 3761 (1970).

    Article  CAS  Google Scholar 

  80. J. Falbe, R. Paatz, and F. Corte, Chem. Ber., 98, 2312 (1965).

    Article  CAS  Google Scholar 

  81. R. Paul, Bull. Soc. Chim. Fr., 911 (1941).

  82. R. Paul and S. Tchelitchef, Bull. Soc. Chim. Fr., 197 (1948).

  83. N. I. Bobrova, Yu. Yu. Belosludtsev, and K. K. Pavnitskii, Zh. Org. Khim., 25, 2073 (1984).

    Google Scholar 

  84. E. Vedejs, M. J. Arnost, and J. P. Hagen, J. Org. Chem., 44, 3230 (1979).

    Article  CAS  Google Scholar 

  85. D. King, J. Chem. Soc., Perkin Trans. 1, 447 (1986).

  86. M. S. Morales-Rios and P. Joseph-Nathan, US Pat. 4803284 (1989); http://ep.espacenet.com/numberSearch?locale=en_EP

  87. L. G. Zepeda, M. Rojas-Gardida, M. S. Morales-Rios, and P. Joseph-Nathan, Tetrahedron, 45, 6439 (1989).

    Article  CAS  Google Scholar 

  88. L. Kh. Vinograd and N. N. Suvorov, Khim. Geterotsikl. Soedin., 1206 (1984). [Chem. Heterocycl. Comp., 20, 984 (1984)].

  89. R. Lukes and J. Trojanek, Chem. Listy, 46, 383 (1952); Chem. Abstr., 47, 4282 (1953).

    CAS  Google Scholar 

  90. J. H. Burckhalter and J. H. Short, J. Org. Chem., 23, 1278 (1958).

    Article  CAS  Google Scholar 

  91. A. Wohl, Ber., 34, 1914 (1901).

    CAS  Google Scholar 

  92. R. H. F. Manske, Can. J. Res., 5, 592 (1931).

    CAS  Google Scholar 

  93. S. Motoki, S. Satsumabayashi, and I. Tajima, Bull. Chem. Soc. Jpn., 37, 646 (1964).

    Article  CAS  Google Scholar 

  94. J. Kato, H. Wakamatsu, R. Iwanaga, and T. Yoshida, J. Chem. Soc. Jpn., Ind. Chem. Sec. (Kogyo Kagaku Zasshi), 64, 2139 (1961).

    CAS  Google Scholar 

  95. M. Hongo, J. Chem. Soc. Jpn., Ind. Chem. Sec. (Kogyo Kagaku Zasshi), 70, 1346 (1967).

    Google Scholar 

  96. Y. Ono, S. Sato, M. Takesada, and H. Wakamatsu, J. Chem. Soc. D, 1255 (1970).

  97. V. B. Del’nik, S. M. Kagna, V. V. Kashina, M. G. Katsnel’son, and G. N. Mishenkova, Zh. Prikl. Khim., 8, 1912 (1978).

    Google Scholar 

  98. J. Kato, H. Wakamatsu, and H. Ishiwara, US Pat. 2978481 (1961); http://ep.espacenet.com/numberSearch?locale=en_EP; Chem. Abstr., 55, 15351 (1961).

    Google Scholar 

  99. O. G. Safiev, D. É. Kruglov, Yu. N. Potapov, and S. S. Zlotskii, Zh. Org. Khim., 20, 1096 (1984).

    CAS  Google Scholar 

  100. A. Saparov, A. Taganlyev, R. Nurberdiev, B. Ibbadulaev, D. Kurbanov, T. Kh. Khodzhalyev, and Yu. K. Khekimov, USSR Inventor’s Certif. 1703648; http://ep.espacenet.com/numberSearch?locale=en_EP; Byul. Izobr., No. 1 (1992).

  101. M. Kawashima and T. Fujisawa, Bull. Chem. Soc. Jpn., 61, 3377 (1988).

    Article  CAS  Google Scholar 

  102. J. M. Varlet, G. Fabre, F. Sauveur, N. Collignon, and P. Savignac, Tetrahedron, 37, 1377 (1981).

    Article  CAS  Google Scholar 

  103. W. A. Ayer, R. Dawe, R. A. Eisner, and K. Furuichi, Can. J. Chem., 54, 473 (1976).

    Article  CAS  Google Scholar 

  104. R. Pineau, J. Recherches CNRS, Labs. Bellevue (Paris), 295 (1951); Chem. Abstr., 46, 416h (1952).

  105. E. J. Witzemann, W. L. Evans, H. Hass, and E. F. Schroeder, Org. Synth., 11, 26 (1931). (Coll. Vol. 2, 137 (1943); http://www.orgsyn.org/orgsyn/pdfs/CV2P0137.pdf)

    Google Scholar 

  106. E. J. Witzemann, W. L. Evans, H. Hass, and E. F. Schroeder, Synthesis of Organic Products [Russian translation], Coll. Vol. 2, Izd. Inostr. Lit., Moscow (1949), p. 67.

    Google Scholar 

  107. U. Faass and H. Hilgert, Chem. Ber., 87, 1343 (1954).

    Article  CAS  Google Scholar 

  108. J. C. Stowell, B. T. King, and H. F. Hauck, J. Org. Chem., 48, 5381 (1983).

    Article  CAS  Google Scholar 

  109. G. Buechi and H. Wuest, J. Org. Chem., 34, 1122 (1969).

    Article  CAS  Google Scholar 

  110. L. Titze and T. Aicher, Preparative Organic Chemistry [Russian translation], Mir, Moscow (1999), p. 540.

    Google Scholar 

  111. J. C. Stowell, D. R. Keith, and B. T. King, Org. Synth., 62, 140 (1984). (Coll. Vol. 7, 59 (1990); http:///www.orgsyn.org/orgsyn/pdfs/CV7P0059.pdf)

    CAS  Google Scholar 

  112. J. C. Stowell and D. R. Keith, Synthesis, 132 (1979).

  113. W. P. Reeves, M. R. White, Synth. Commun., 6, 193 (1976).

    Article  CAS  Google Scholar 

  114. A. Wohl, Ber., 39, 1951 (1906).

    Google Scholar 

  115. E. Anderson and B. Capon, J. Chem. Soc., Perkin Trans. 2, 515 (1972).

  116. L. Friedman and H. Shechter, J. Org. Chem., 25, 877 (1960).

    Article  CAS  Google Scholar 

  117. G. Chelucci, Synthesis, 474 (1991).

  118. M. Ohtani, M. Fuji, and O. Osaka, US Pat. 6787545 (2004); http://ep.espacenet.com/numberSearch?locale=en_EP

  119. N. Ono (editor), The Nitro Group in Organic Synthesis, John Wiley-VCH, New York (2001), p. 170.

    Google Scholar 

  120. R. Ballini, P. Marziali, and A. Mozzicafreddo, J. Org. Chem., 61, 3209 (1996).

    Article  CAS  Google Scholar 

  121. L. El Blidi, D. Crestia, E. Gallienne, C. Demuynck, J. Bolte, and M. Lemaire, Tetrahedron: Asymm., 15, 2951 (2004).

    Article  CAS  Google Scholar 

  122. H. Shechter, D. E. Ley, and L. Zeldin, J. Am. Chem. Soc., 74, 3664 (1952).

    Article  CAS  Google Scholar 

  123. D. T. Warner and O. A. Moe, J. Am. Chem. Soc., 74, 1064 (1952).

    Article  CAS  Google Scholar 

  124. T. Miyakoshi, Synthesis, 1024 (1986).

  125. C. Hauh-Jyun Candy, T. Applewhite, B. Jayachandran, and K. L. Kirk, J. Fluor. Chem., 92, 41 (1998).

    Article  Google Scholar 

  126. T. Miyakoshi, Synthesis, 766 (1986).

  127. A. Horni, I. Hubaek, and M. Hesse, Helv. Chim. Acta, 77, 579 (1994).

    Article  CAS  Google Scholar 

  128. T. Miyakoshi and S. Saito, Oil Chem. (Yukagaku), 31, 231 (1982); Chem. Abstr., 97, 38526 (1982).

    CAS  Google Scholar 

  129. R. Lukes and J. Trojanek, Collect. Czech. Chem. Commun., 25, 2248 (1960).

    CAS  Google Scholar 

  130. R. Lukes and J. Kovar, Collect. Czech. Chem. Commun., 21, 1317 (1956).

    CAS  Google Scholar 

  131. C. F. H. Allen and J. H. Clark, Org. Synth., 24, 3 (1944).

    CAS  Google Scholar 

  132. C. Struve and C. Christophersen, Heterocycles, 60, 1907 (2003).

    CAS  Google Scholar 

  133. F. Sternfeld, A. R. Guiblin, R. A. Jelley, V. G. Matassa, A. J. Reeve, P. A. Hunt, M. S. Beer, A. Heald, J. A. Stanton, B. Sohal, A. P. Watt, and L. J. Street, J. Med. Chem., 42, 677 (1999).

    Article  CAS  Google Scholar 

  134. R. Baker and S. Bourrain, US Pat. 5854268 (1998); http://ep.espacenet.com/numberSearch?locale=en_EP

  135. O. H. Johnson and J. R. Holum, J. Org. Chem., 23, 738 (1958).

    Article  CAS  Google Scholar 

  136. A. Le Coq and A. Gorgues, Org. Synth., 59, 10 (1979). (Coll. Vol. 6, 954 (1988); http:/www.orgsyn.org/orgsyn/pdfs/CV6P0954.pdf)

    Google Scholar 

  137. D. Keglević and B. Leonhard, Croat. Chem. Acta, 35, 175 (1963).

    Google Scholar 

  138. T. Masahiro and R. Yoshida, Jpn. Pat. 6809529 (1968); Chem. Abstr., 69, 107070 (1968).

  139. S. Bhattacharyya, Tetrahedron Lett., 35, 2401 (1994).

    Article  CAS  Google Scholar 

  140. D. Desaty and D. Keglević, Croat. Chem. Acta, 36, 103 (1964).

    CAS  Google Scholar 

  141. T. Hoshino and T. Kobayashi, Liebigs Ann. Chem., 520, 11 (1935).

    Article  CAS  Google Scholar 

  142. D. Keglević, N. Stojanac, and D. Desaty, Croat. Chem. Acta, 33, 83 (1961).

    Google Scholar 

  143. Y. C. Xu, J. M. Schaus, C. Walker, J. Krushinski, N. Adham, J. M. Zgombick, S. X. Liang, D. T. Kohlman, and J. E. Audia, J. Med. Chem., 42, 526 (1999).

    Article  CAS  Google Scholar 

  144. T. P. Karpetsky and E. H. White, Tetrahedron, 29, 3761 (1973).

    Article  CAS  Google Scholar 

  145. A. L. Mndzhoyan and N. M. Divonyan, Syntheses of Heterocyclic Compounds [in Russian], Issue 5, Izd. Acad. Nauk ArmSSR, Erevan (1972), p. 18.

    Google Scholar 

  146. E. Tietze, DE730237 (1943); http://ep.espacenet.com/numberSearch?locale=en_EP

  147. Reagents and Specially Pure Substances [in Russian], NIITEKHIM, Vol. 6 (1978), p. 4.

  148. M. Jurgen and W. Horst, DE 3415322 (1985); http://ep.espacenet.com/numberSearch?locale=en_EP

  149. C. D. Lunsford, R. S. Murphey, and E. K. Rose, J. Org. Chem., 22, 1225 (1957).

    Article  CAS  Google Scholar 

  150. J. Ch. Eriks, H. Van der Goot, G. J. Sterk, and H. Timmerman, J. Med. Chem., 35, 3239 (1992).

    Article  CAS  Google Scholar 

  151. Cedona Pharm BV, W09110657 (1991); http://ep.espacenet.com/numberSearch?locale=en_EP

  152. S. Sugiura, S. Inoue, Y. Hayashi, Y. Kishi, and T. Goto, Tetrahedron, 25, 5155 (1969).

    Article  CAS  Google Scholar 

  153. T. Nagata and K. Tanaka, Inorg. Chem., 39, 3515 (2000).

    Article  CAS  Google Scholar 

  154. M. Wada, H. Nakai, Y. Sato, Y. Hatanaka, and Y. Kanaoka, Tetrahedron, 39, 2691 (1983).

    Article  CAS  Google Scholar 

  155. K. Balenovic, I. Jambresic, and I. Furic, J. Org. Chem., 17, 1459 (1952).

    Article  CAS  Google Scholar 

  156. F. E. King, P. L’Ecuyer, and H. T. Openshaw, J. Chem. Soc., 352 (1936).

  157. Sterling Drug Inc., Brit. Pat. 895430 (1962); http://ep.espacenet.com/numberSearch?locale=en_EP

  158. R. Bonnett, V. M. Clark, A. Giddey, and A. Todd, J. Chem. Soc, 2087 (1959).

  159. Y. Nomura, K. Ogawa, Y. Takeuchi, and S. Tomoda, Chem. Lett, 693 (1977).

  160. H. Poisel, Monatsh. Chem., 109, 925 (1978).

    Article  CAS  Google Scholar 

  161. G. A. Kraus and K. Neuenschwander, J. Org. Chem., 46, 4791 (1981).

    Article  CAS  Google Scholar 

  162. D. W. Fuhlhage and C. A. VanderWerf, J. Am. Chem. Soc., 80, 6249 (1958).

    Article  CAS  Google Scholar 

  163. A. Luttringhaus, J. Jander, and R. Schneider, Chem. Ber., 92, 1756 (1959).

    Article  CAS  Google Scholar 

  164. G. P. Claxton, L. Allen, and J. M. Grisar, Org. Synth., 56, 118 (1977). (Coll. Vol. 6, 968 (1988); http:/www.orgsyn.org/orgsyn/pdfs/CV6P0968.pdf)

    CAS  Google Scholar 

  165. W. Klaus and M. Michael, US Pat 4123434 (1978); http://ep.espacenet.com/numberSearch?locale=en_EP, Chem. Abstr., 88, 152670 (1978).

  166. K. Ogawa, Y. Nomura, Y. Takeuchi, and Sh. Tomoda, J. Chem. Soc, Perkin Trans. 1, 3031 (1982).

  167. J. G. Delcros, S. Tomasi, S. Carrington, B. Martin, J. Renault, I. S. Blagbrough, and P. Uriac, J. Med. Chem., 45, 5098 (2002).

    Article  CAS  Google Scholar 

  168. A. M. Schmidt and P. Eilbracht, Org. Biomol. Chem., 12, 2333 (2005); see also supplementary information.

    Article  CAS  Google Scholar 

  169. J. B. Gimeno, Diss. PhD, Barcelona, Italy, 2002; http://www.tdx.cesca.es/TDX-0309103-193517/

  170. T. Nagasaka, H. Tamano, T. Maekawa, and F. Hamaguchi, Heterocycles, 26, 617 (1987).

    CAS  Google Scholar 

  171. D. F. Oliveira, P. C. M. L. Miranda, and C. R. D. Correia, J. Org. Chem., 64, 6646 (1999); see also supplementary information.

    Article  CAS  Google Scholar 

  172. S. Sato, Nippon Kagaku Zasshi, 90, 404 (1969); Chem. Abstr., 71, 21828g (1969).

    CAS  Google Scholar 

  173. D. Keirs, D. Moffat, K. Overton, and R. Tomanek, J. Chem. Soc, Perkin Trans. 1, 1041 (1991).

  174. T. Nagasaka, H. Tamano, and F. Hamaguchi, Heterocycles, 14, 1231 (1986).

    Google Scholar 

  175. T. Shono, Y. Matsumura, and K. Tsubata, Org. Synth., 63, 206 (1985). (Coll. Vol. 7, 307 (1990); http:/www.orgsyn.org/orgsyn/pdfs/CV7P0307.pdf)

    CAS  Google Scholar 

  176. S. Yoshifuji, K. Tanaka, T. Kawai, and Y. Nitta, Chem. Pharm. Bull, 34, 3873 (1986).

    CAS  Google Scholar 

  177. W. Marais and C. W. Holzapfel, Synth. Commun., 28, 3681 (1998).

    Article  CAS  Google Scholar 

  178. T. Shono, Tetrahedron, 40, 811 (1984).

    Article  CAS  Google Scholar 

  179. T. Shono, Y. Matsumura, T. Kanasawa, M. Habuka, K. Unchida, and K. Toyoda, J. Chem. Res., 320 (1984).

  180. M. Mitzlaff, K. Warning, and H. Jensen, Liebigs Ann. Chem., 1713 (1978).

  181. T. Shono, H. Hamaguchi, and Y. Matsumura, J. Am. Chem. Soc., 97, 4264 (1975). (http:/www.orgsyn.org/orgsyn/pdfs/v80p0085.pdf)

    Article  CAS  Google Scholar 

  182. T. Shono, Y. Matsumura, K. Tsubata, K. Uchida, T. Kanazawa, and K. Tsuda, J. Org. Chem., 49, 3711 (1984).

    Article  CAS  Google Scholar 

  183. T. Shono, Y. Mataumura, and T. Kanazawa, Tetrahedron Lett., 24, 1259 (1983).

    Article  CAS  Google Scholar 

  184. R. K. Dieter and R. R. Sharma, J. Org. Chem., 61, 4180 (1996).

    Article  CAS  Google Scholar 

  185. J. Ahman and P. Somfai, Tetrahedron, 48, 9537 (1992).

    Article  Google Scholar 

  186. J. C. Hubert, J. B. P. A. Wijnberg, and W. N. Speckamp, Tetrahedron, 31, 1437 (1975).

    Article  CAS  Google Scholar 

  187. A. K. Heinz, Tetrahedron Lett., 34, 7721 (1993).

    Article  Google Scholar 

  188. A. R. Chamberlin, H. D. Nguyen, and J. Y. L. Chung, J. Org. Chem., 49, 1682 (1984).

    Article  CAS  Google Scholar 

  189. M. V. Chiesa, L. Manzoni, and C. Scolastico, Synlett, 441 (1996).

  190. J. K. Stille and Y. Becker, J. Org. Chem., 45, 2139 (1980).

    Article  CAS  Google Scholar 

  191. M. L. Ferguson, D. J. O’Leary, and R. H. Grubbs, Org. Synth., 80, 85 (2003); http:/www.orgsyn.org/orgsyn/pdfs/v80p0085.pdf

    CAS  Google Scholar 

  192. A. I. Meyers, J. S. Warmus, and G. J. Dilley, Org. Synth., 73, 246 (1996) (Coll. Vol. 9, 666 (1998); http:/www.orgsyn.org/orgsyn/pdfs/CV9P0666.pdf)

    CAS  Google Scholar 

  193. T. Shono, Y. Matsumura, K. Tsubata, Y. Sugihara, S. Yamane, T. Kanazawa, and T. Aoki, J. Am. Chem. Soc., 104, 6697 (1982).

    Article  CAS  Google Scholar 

  194. I. Ojima and Zh. Zhang, J. Organomet. Chem., 417, 253 (1991).

    Article  CAS  Google Scholar 

  195. Y. Becker, A. Eisenstadt, and J. K. Stille, J. Org. Chem., 45, 2145 (1980).

    Article  CAS  Google Scholar 

  196. S. Sato, M. Takesada, and H. Wakamcitau, Nippon Kagaku Zasshi, 90, 579 (1969); Chem. Abstr., 71, 49178 (1969).

    CAS  Google Scholar 

  197. P. Köhling, A. M. Schmidt, and P. Eilbracht, Org. Lett., 5, 3213 (2003); see also supplementary information.

    Article  CAS  Google Scholar 

  198. A. M. Schmidt and P. Eilbracht, J. Org. Chem., 70, 5528 (2005); see also supplementary information.

    Article  CAS  Google Scholar 

  199. G. Verspui, G. Elbertse, F. A. Sheldon, M. A. P. J. Hacking, and R. A. Sheldon, Chem. Commun., 1363 (2000); see also supplementary information.

  200. M. Kranenburg, Organometallics, 14, 3081 (1995).

    Article  CAS  Google Scholar 

  201. A. J. Ewins, J. Chem. Soc., 270 (1911).

  202. C. Schopf and H. Steuer, Liebigs Ann. Chem., 558, 124 (1947).

    Article  CAS  Google Scholar 

  203. E. Späth and E. Lederer, Ber., 63, 2102 (1930).

    Google Scholar 

  204. K. Eiter and O. Svierak, Monatsh. Chem., 83, 1453 (1952).

    Article  CAS  Google Scholar 

  205. U. Hörlein, Chem. Ber., 87, 463 (1954).

    Article  Google Scholar 

  206. G. Bernini, Ann. Chim. (Rome), 43, 559 (1953).

    CAS  Google Scholar 

  207. Z. J. Vejdelek and L. Tuma, Ceskoslov. farm., 4, 510 (1955).

    Google Scholar 

  208. J. Quadbeck and E. Röhm, Hoppe-Seyler’s Z. Physiol. Chem., 297, 229 (1954).

    CAS  Google Scholar 

  209. T. Hoshino, T. Kobayashi, and Y. Kotake, Liebigs Ann. Chem., 516, 81 (1935).

    Article  CAS  Google Scholar 

  210. E. Späth and E. Lederer, Ber., 63, 120 (1930).

    Google Scholar 

  211. E. Adlerová, J. Hněvsová, P. Novák, and S. Rajšner, Collect. Czech. Chem. Commun., 25, 784 (1960).

    Google Scholar 

  212. K. Eiter and E. Nezval, Monatsh. Chem., 81, 404 (1950).

    Article  CAS  Google Scholar 

  213. K. L. Rinehart, Jr., J. Kobayashi, G. C. Harbour, J. Gilmore, M. Mascal, T. G. Holt, L. S. Shield, and F. Lafargue, J. Am. Chem. Soc., 109, 3378 (1987).

    Article  CAS  Google Scholar 

  214. K. J. Hwang and T. S. Lee, Synth. Commun., 29, 2099 (1999).

    Article  CAS  Google Scholar 

  215. D. Desaty and D. Keglević, Croat. Chem. Acta, 37, 25 (1965).

    CAS  Google Scholar 

  216. D. Keglević and D. Goleš, Croat. Chem. Acta, 42, 513 (1970).

    Google Scholar 

  217. D. Desaty, O. Hadžija, S. Iskric, D. Keglević, and S. Kveder, Biochim. Biophys. Acta., 62, 179 (1962).

    Article  CAS  Google Scholar 

  218. Y. Y. Liu and M. Minich, J. Labelled Comp. Radiopharm., 18, 791 (1981).

    Article  CAS  Google Scholar 

  219. J. B. Blair, D. K. Orbaugh, D. M. Lewicka, M. G. Cumbay, V. J. Watts, E. L. Barker, and D. E. Nichols, J. Med. Chem., 43, 4701 (2000).

    Article  CAS  Google Scholar 

  220. L. J. Street, R. Baker, W. B. Davey, A. R. Guiblin, R. A. Jelley, A. J. Reeve, H. Routledge, F. Sternfeld, and A. P. Watt, J. Med. Chem., 38, 1799 (1995).

    Article  CAS  Google Scholar 

  221. R. Baker, V. G. Matassa, A. J. Reeve, F. Sternfeld, and L. J. Street, Eur. Pat. 0581538 (1994); http://ep.espacenet.com/numberSearch?locale=en_EP

  222. L. Kh. Vinograd and N. N. Suvorov, USSR Inventor’s Certif. 992513; http://ep.espacenet.com/numberSearch?locale=en_EP, Byul. Izobr., No. 4 (1983).

  223. D. E. Bays and C. F. Webb, Pat. GB 2168347 (1986); http://ep.espacenet.com/numberSearch?locale=en_EP

  224. Glaxo Group Ltd., Pat. GB 2082175 (1982); http://ep.espacenet.com/numberSearch?locale=en_EP

  225. B. G. Szczepankiewicz and C. H. Heathcock, Tetrahedron, 53, 8853 (1997).

    Article  CAS  Google Scholar 

  226. I. I. Grandberg and S. B. Nikitina, Khim. Geterotsikl. Soedin., 1201 (1971). [Chem. Heterocycl. Comp., 7, 1128 (1971)].

    Google Scholar 

  227. G. Palmisano, B. Danieli, G. Lesma, and D. Passarella, Tetrahedron, 45, 3583 (1989).

    Article  CAS  Google Scholar 

  228. F. Masumi, H. Takeuchi, S. Kondo, K. Suzuki, and S. Yamada, Chem. Pharm. Bull., 30, 3831 (1982).

    CAS  Google Scholar 

  229. H. Eto, Ch. Eguchi, and T. Kagawa, Bull. Chem. Soc. Jpn., 62, 961 (1989).

    Article  CAS  Google Scholar 

  230. I. I. Grandberg and S. B. Nikitina, Khim. Geterotsikl. Soedin., 54 (1971). [Chem. Heterocycl. Comp., 7, 50 (1971)].

    Google Scholar 

  231. I. I. Grandberg, T. I. Zuyanova, N. I. Afonina, and T. A. Ivanova, Dokl. Akad. Nauk, 176, 583 (1967).

    CAS  Google Scholar 

  232. J. Bosch, T. Roca, M. Armengol, and D. F. Forner, Tetrahedron, 57, 1041 (2001).

    Article  CAS  Google Scholar 

  233. E. Shaw and D. W. Woolley, J. Am. Chem. Soc., 75, 1877 (1953).

    Article  CAS  Google Scholar 

  234. P. Bela, B. Istvan, S. J. Csaba, S. Istvan, and T. Laszlo, Heterocycles, 48, 1139 (1998).

    Article  Google Scholar 

  235. F. D. Albinson, J. W. M. MacKinnon, and D. L. Crookes, Eur. Pat. 0462837 (1991); http://ep.espacenet.com/numberSearch?locale=en_EP, Chem. Abstr., 116, 106088 (1992).

    Google Scholar 

  236. J. L. Castro, R. Baker, A. R. Guiblin, S. C. Hobbs, and M. R. Jenkins, J. Med. Chem., 37, 3023 (1994).

    Article  CAS  Google Scholar 

  237. J. L. Castro and V. G. Matassa, Tetrahedron Lett., 34, 4705 (1993).

    Article  CAS  Google Scholar 

  238. L. J. Street, R. Baker, J. L. Castro, M. S. Chambers, A. R. Guiblin, S. C. Hobbs, V. G. Matassa, A. J. Reeve, and M. S. Beer, J. Med. Chem., 36, 1529 (1993).

    Article  CAS  Google Scholar 

  239. J. Buckingham, R. C. Glen, A. P. Hill, R. M. Hyde, G. R. Martin, A. D. Robertson, J. A. Salmon, and P. M. Woollard, J. Med. Chem., 38, 3566 (1995).

    Article  CAS  Google Scholar 

  240. A. Skwierawska and E. Paluszkiewicz, Polish J. Chem., 77, 329 (2003).

    CAS  Google Scholar 

  241. Merck & Co. Inc., US Pat. 3014043 (1961); http://ep.espacenet.com/numberSearch?locale=en_EP, Chem. Abstr., 56, 15486 (1962).

    Google Scholar 

  242. Warner Lambert Pharmaceutical, US Pat. 3037031 (1962); http://ep.espacenet.com/numberSearch?locale=en_EP

  243. N. N. Suvorov, L. M. Morozovskaya, and L. I. Ershova, Zh. Obshch. Khim., 32, 2556 (1962).

    CAS  Google Scholar 

  244. M. Kawase, A. K. Sinhababu, E. M. McGhee, T. Milby, and R. T. Borchardt, J. Med. Chem., 33, 2204 (1990).

    Article  CAS  Google Scholar 

  245. A. Buzas and C. Herisson, Synthesis, 129 (1977).

  246. A. W. Oxford and B. Evans, US Pat. 4994483 (1991); http://ep.espacenet.com/numberSearch?locale=en_EP

  247. Glaxo Group Ltd., US Pat. 4816470 (1989); http://ep.espacenet.com/numberSearch?locale=en_EP

  248. O. A. Moe and D. T. Warner, J. Am. Chem. Soc., 70, 2763 (1948).

    Article  CAS  Google Scholar 

  249. K. H. Poe, O. Salcher, and F. Lingens, Liebigs Ann. Chem., 233 (1981).

  250. J. Porter, J. Dykert, and J. Rivier, Int. J. Peptide Protein Res., 30, 13 (1987).

    CAS  Google Scholar 

  251. N. N. Suvorov, L. M. Morozovskaya, and N. P. Sorokina, Zh. Obshch. Khim., 31, 936 (1961).

    CAS  Google Scholar 

  252. D. T. Warner and O. A. Moe, J. Am. Chem. Soc., 70, 2765 (1948).

    Article  CAS  Google Scholar 

  253. H. Rinderknecht and C. Niemann, J. Am. Chem. Soc,, 72, 2296 (1950).

    Article  CAS  Google Scholar 

  254. H. R. Snyder, H. R. Beilfuss, and J. K. Williams, J. Am. Chem. Soc., 75, 1873 (1953).

    Article  CAS  Google Scholar 

  255. M. Lee and R. S. Phillips, Bioorg. Med. Chem. Lett., 1, 477 (1991).

    Article  CAS  Google Scholar 

  256. C. Cavallini and V. Ravenna, Farmaco Ed. Sci., 13, 105 (1958); Chem. Abstr., 52, 20126 (1958).

    CAS  Google Scholar 

  257. S. P. Hiremath and S. S. Siddapa, J. Karnatak Univ., 6, 1 (1962); Chem. Abstr., 59, 8855 (1963).

    CAS  Google Scholar 

  258. S. Gorohovsky, S. Meir, V. Shkoulev, G. Byk, and G. Gellerman, Synlett, 1411 (2003).

  259. T. Okuda, Bull. Chem. Soc. Jpn., 30, 358 (1957).

    Article  CAS  Google Scholar 

  260. L. De Bellis and M. L. Stein, Ann. Chim. (Rome), 51, 663 (1961); Chem. Abstr., 56, 11544 (1962).

    Google Scholar 

  261. P. Remuzon, C. Dussy, J. P. Jacquet, M. Soumeillant, and D. Bouzard, Tetrahedron Lett., 36, 6227 (1995).

    Article  CAS  Google Scholar 

  262. P. R. Brodfuehrer, B. C. Chen, T. R. Sattelberg, P. R. Smith, J. P. Reddy, J. K. Thottathil, and S. J. Wang, J. Org. Chem., 62, 9192 (1997).

    Article  CAS  Google Scholar 

  263. J.-M. Fu, Eur. Pat. 1411925 (2004); http://ep.espacenet.com/numberSearch?locale=en_EP

  264. N. J. Holman and Ch. L. Friend, Eur. Pat. 1226116 (2002); http://ep.espacenet.com/numberSearch?locale=en_EP

  265. A. W. Oxford, US Pat. 5037845 (1991); http://ep.espacenet.com/numberSearch?locale=en_EP, Chem. Abstr., 105, 78831 (1986).

  266. S. Wagaw, B. H. Yang, and S. L. Buchwald, J. Am. Chem. Soc., 120, 6621(1998).

    Article  CAS  Google Scholar 

  267. S. Wagaw, B. H. Yang, and S. L. Buchwald, J. Am. Chem. Soc., 121, 10251 (1998).

    Article  CAS  Google Scholar 

  268. M. Wolter, A. Klapars, and S. L. Buchwald, Org. Lett., 3, 3808 (2001).

    Article  CAS  Google Scholar 

  269. A. M. Schmidt, Diss. Dr. rer. nat., Dortmund, Germany (2005); http://hdl.handle.net/2003/22161

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  1. Institute of Physiologically Active Substances, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russia, 142432

    T. I. Bidylo

  2. M. V. Lomonosov Moscow State University, Moscow, 119992, Russia

    M. A. Yurovskaya

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 493–538, April, 2008.

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Bidylo, T.I., Yurovskaya, M.A. Synthesis of tryptamines by the Fischer method using synthetic precursors and latent forms of amino-butanal (review). Chem Heterocycl Comp 44, 379–418 (2008). https://doi.org/10.1007/s10593-008-0057-x

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