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Synthesis of pyrroles from heterocyclic compounds (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Current information on methods of forming a pyrrole ring from heterocyclic compounds is systematized and generalized. Reaction schemes are discussed.

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Literature Cited

  1. A. Gossauer, The Chemistry of Pyrroles (in German), Springer-Verlag, Berlin, Heidelberg, New York (1974).

    Google Scholar 

  2. R. A. Jones and G. P. Bean, The Chemistry of Pyrroles, Acad. Press, London, New York, San Franciso (1977).

    Google Scholar 

  3. B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles (in Russian), Nauka, Novosibirsk (1984).

    Google Scholar 

  4. Yu. K. Yur'ev and I. P. Gragerov, Zh. Obshch. Khim., 20, 171 (1950).

    Google Scholar 

  5. B. A. Trofimov and A. I. Mikhaleva, Khim. Geterotsikl. Khim., No. 10, 1299 (1980).

    Google Scholar 

  6. R. J. Tedesche, Encyclopedia of Physical Science and Technology, Acad. Press, San Diego (1987), Vol. 1, p. 25.

    Google Scholar 

  7. B. A. Trofimov, S. E. Korostova, A. I. Mikhaleva, L. N. Sobenina, V. V. Shcherbakov, and M. V. Sigalov, Khim. Geterotsikl. Soed., No. 2, 276 (1983).

    Google Scholar 

  8. S. E. Korostova, A. I. Mikhaleva, and L. N. Sobenina, IV All-Union Symposium on Organic Synthesis: Abstracts [in Russian], Moscow (1984), p. 110.

  9. B. A. Trofimov, S. G. Shevchenko, S. E. Korostova, A. I. Mikhaleva, and V. V. Shcherbakov, Khim. Geterotsikl. Soed., No. 11, 1573 (1985).

    Google Scholar 

  10. T. N. Borisova, Dissertation for Candidate of Chem. Sci. [in Russian], Moscow (1987).

  11. T. N. Borisova, A. V. Varlamov, and N. S. Prostakov, I All-Union Conference on the Chemistry, Biochemistry, and Pharmacology of Indole Derivatives: Abstracts (in Russian), Tbilisi (1986), p. 39.

  12. T. N. Borisova, VIII Young People's Conference on Synthetic and Natural Physiologically Active Compounds: Abstracts (in Russian), Erevan (1986), p. 33.

  13. A. Padwa and Y. Kulkarni, Tetrahedron Lett., No. 2, 107 (1979).

    Google Scholar 

  14. A. Laurent, P. Mison, A. Nafti, and N. Pellissier, Tetrahedron Lett., No. 18, 1587 (1979).

    Google Scholar 

  15. A. Laurent, P. Mison, A. Nafti, and N. Pellissier, Tetrahedron Lett., No. 23, 655 (1982).

    Google Scholar 

  16. A. Laurent, Bull. Soc. Chim. Belges, 92, 797 (1983).

    Google Scholar 

  17. U. S. Patent 3869470, E. A. Zuech; Chem. Abstr. 83, 9776 (1975).

    Google Scholar 

  18. J. P. Carson, U. S. Patent 3957818; Chem. Abstr. 85, 108517 (1976).

    Google Scholar 

  19. R. M. Acheson, M. J. Ferris, S. R. Critchley, and D. J. Watkin, J. Chem. Soc., Perkin Trans. 2, No. 2, 326 (1980).

    Google Scholar 

  20. J. Cossy and J. P. Pete, Tetrahedron Lett., No. 49, 4941 (1978).

    Google Scholar 

  21. E. Campaigne and G. M. Shutske, J. Heterocycl. Chem., 11, 929 (1974).

    Google Scholar 

  22. K. S. Kochhar and H. W. Pinnick, J. Org. Chem., 49, 3222 (1984).

    Google Scholar 

  23. M. Miocque, M. D. Engenieres, and J. Sauzieres, Bull. Chem. Soc. Chim. France, No. 7–8, 1777 (1975).

    Google Scholar 

  24. J. W. ApSimon, D. G. Durham, and A. H. Rees, J. Chem. Soc., Perkin Trans. 1, No. 12, 1588 (1978).

    Google Scholar 

  25. R. Grigg, H. Q. N. Gunaratne, and J. Kemp, Tetrahedron Lett., 25, 99 (1984).

    Google Scholar 

  26. K. Rehse and G. Mattern, Arch. Pharm., 311, 364 (1978).

    Google Scholar 

  27. G. Wittig and A. Hesse, Annalen, No. 10, 1831 (1975).

    Google Scholar 

  28. A. R. Krawezyk and J. T. Wrobel, Pol. J. Chem., 55, 1363 (1981).

    Google Scholar 

  29. W. Flitsch and F. Kappenberg, Chem. Ber., 111, 2401 (1978).

    Google Scholar 

  30. T. Schmidlin and C. Tamm, Helv. Chim. Acta, 63, 121 (1980).

    Google Scholar 

  31. H. Wolfers, U. Kraatz, and F. Korte, Chem. Ber., 109, 1061 (1976).

    Google Scholar 

  32. C. A. Wilson and T. A. Bryson, J. Org. Chem., 40, 800 (1975).

    Google Scholar 

  33. G. Dannhardt and R. Obergrusberger, Arch. Pharm., 317, 143 (1984).

    Google Scholar 

  34. F. De Sarlo, A. Brandi, and P. Mascagni, Synthesis, No. 7, 561 (1981).

    Google Scholar 

  35. B. F. Kukharev, V. K. Stankevich, and V. A. Kukhareva, Khim. Geterotsikl. Soed., No. 5, 700 (1984).

    Google Scholar 

  36. B. F. Kukharev and A. S. Atavin, Zh. Org. Khim., 10, 670 (1974).

    Google Scholar 

  37. B. F. Kukharev and A. S. Atavin, Khim. Geterotsikl. Soed., No. 11, 1580 (1973).

    Google Scholar 

  38. B. F. Kukharev, V. K. Stankevich, and V. A. Kukhareva, USSR Author's Certificate 1047901; Byull. Izobret., No. 38, 85 (1983).

  39. B. F. Kukharev, V. K. Stankevich, and V. A. Kukhareva, Khim. Geterotsikl. Soed., No. 4, 533 (1986).

    Google Scholar 

  40. B. A. Trofimov, Zh. Org. Khim., 22, 1991 (1986).

    Google Scholar 

  41. P. Barker P. Gendler, and H. Rapoport, J. Org. Chem., 43, 4849 (1978).

    Google Scholar 

  42. A. Padwa, U. Chiacchio, and Ven Katramanan, J. Chem. Soc., Chem. Commun., No. 16, 1108 (1985).

    Google Scholar 

  43. I. A. Benages and S. M. Albonico, J. Org. Chem., 43, 4273 (1978).

    Google Scholar 

  44. O. Yebdri, O. Henri-Rousseau, and F. Texier, Tetrahedron Lett., 24, 369 (1983).

    Google Scholar 

  45. H. C. Berk and J. E. Franz, Synth. Commun., 11, 267 (1981).

    Google Scholar 

  46. H. Matsukubo and H. Kato, J. Chem. Soc., Chem. Commun., No. 20, 840 (1975).

    Google Scholar 

  47. A. O. Fitton, J. R. Frost, H. Suschitzky, and P. G. Houghton, Synthesis, No. 2, 133 (1977).

    Google Scholar 

  48. H. J. Wollweber and C. Wentrup, J. Org. Chem., 50, 2041 (1985).

    Google Scholar 

  49. K. Hatada, M. Shimada, K. Fujita, Y. Ono, and T. Keii, Chem. Lett., No. 5, 439 (1974).

    Google Scholar 

  50. M. Kubo and K. Yasuda, Jpn. Patent 75112362; Chem. Abstr., 84, 59180 (1976).

    Google Scholar 

  51. M. Kubo and K. Yasuda, Jpn. Patent 75112361; Chem. Abstr. 84, 59181 (1976).

    Google Scholar 

  52. Daicel Chemical Industries, Jpn. Patent 5890548; Chem. Abstr. 99, 105121 (1983).

    Google Scholar 

  53. J. F. Blount, D. L. Coffen, and D. A. Katonak, J. Org. Chem., 43, 3821 (1978).

    Google Scholar 

  54. S. I. Burmistrov and V. M. Sannikova, Voprosy Khim. Khim. Tekhnol., No. 54, 20 (1978).

    Google Scholar 

  55. é. Baum, T. E. Goldovskaya, V. G. Kul'nevich, and O. V. Maiorova, Khim. Geterotsikl. Soed., No. 8, 1062 (1981).

    Google Scholar 

  56. G. P. Rizzi, J. Agric. Food Chem., 22, 279 (1974).

    Google Scholar 

  57. N. S. Kozlov, L. I. Moiseenok, and S. I. Kozintsev, Dokl. Akad. Nauk SSSR, 252, 1132 (1980).

    Google Scholar 

  58. F. Boberg, K. H. Garburg, A. Garming, K. J. Görlich, E. Pipereit and M. D. Ruhr, Annalen, No. 6, 1119 (1985).

    Google Scholar 

  59. V. M. Colburn, B. Iddon, H. Suschitzky, and P. T. Gallagher, J. Chem. Soc., Chem. Commun., No. 11, 453 (1978).

    Google Scholar 

  60. I. S. Monakhova and A. V. Malev, Khim. Geterotsikl. Soed., No. 3, 358 (1975).

    Google Scholar 

  61. I. Jirkovsky and R. Baudy, Synthesis, No. 6, 481 (1981).

    Google Scholar 

  62. Dainippon Pharmaceutical Co., Jpn. Patent 8270865; Chem. Abstr., 97, 162809 (1982).

    Google Scholar 

  63. W. Himmele, A. Freidenrang, H. Siegel, and D. Degner, FRG Patent 2645171; Chem. Abstr., 89, 24139 (1978).

    Google Scholar 

  64. K. A. Jacgge, F. Ostermayer, and H. Schroeter, Swed. Patent 579045; Chem. Abstr., 24, [sic], 1560 (1974).

    Google Scholar 

  65. J. C. Gehret and K. Gubler, Great Br. Patent 2134518; Chem. Abstr., 102, 6194 (1985).

    Google Scholar 

  66. M. Artico, F. Corell, S. Massa, and G. Stefancich, Synthesis, No. 11, 931 (1983).

    Google Scholar 

  67. Y. Kawamatsu, H. Sugihara, N. Matsumoto, and Y. Hamuro, Jpn. Patent 7424065; Chem. Abstr., 83, 86270 (1975).

    Google Scholar 

  68. H. Sugihara, N. Matsumoto, Y. Hamuro, and Y. Kawamatsu, Arzneim.-Forsch., 24, 1560 (1974).

    Google Scholar 

  69. Merck and Co. Inc., Aus. Patent 319934; Chem. Abstr., 83, 170662 (1975).

    Google Scholar 

  70. J. H. Sarett and W. V. Ruyle, SAR Patent 7201129; Chem. Abstr., 81, 63478 (1974).

    Google Scholar 

  71. Lipha, French Patent 2371924; Chem. Abstr., 90, 151980 (1979).

    Google Scholar 

  72. E. Szarvasi and D. Festal, Patent 2751178; Chem. Abstr., 89, 109076 (1978).

    Google Scholar 

  73. D. Lenke, C. D. Mueller, K. H. Geiss, and J. U. Bliesener, FRG Patent 2914615; Chem. Abstr., 94, 83939 (1981).

    Google Scholar 

  74. J. U. Bliesener, K. H. Geiss, D. Lenke, and C. D. Mueller, FRG Patent 2831850; Chem. Abstr., 93, 71546 (1980).

    Google Scholar 

  75. W. Vollenberg and R. Beckmann, FRG Patent 2427614; Chem. Abstr., 84, 105387 (1976).

    Google Scholar 

  76. R. E. Johnson, Belg. Patent 816542; Chem. Abstr., 83, 97007 (1975).

    Google Scholar 

  77. R. E. Johnson, FRG Patent 2429923; Chem. Abstr., 82, 156057 (1975).

    Google Scholar 

  78. W. Merkel, D. Bormann, and D. Mania, FRG Patent 2718494; Chem. Abstr., 90, 103817 (1979).

    Google Scholar 

  79. W. Merkel, D. Bormann, D. Mania, and R. Muschaweck, FRG Patent 2658766; Chem. Abstr., 89, 109082 (1978).

    Google Scholar 

  80. E. Habicht, FRG Patent 2756783; Chem. Abstr., 89, 146759 (1978).

    Google Scholar 

  81. S. Faroog, J. Drabek, L. Gsell, W. Meyer, and F. Karrer, FRG Patent 2647368; Chem. Abstr., 87, 84808 (1977).

    Google Scholar 

  82. Matsushita Electrical Industrial Co., Belg. Patent 896769; Chem. Abstr., 100, 85589 (1984).

    Google Scholar 

  83. A. Hamdan and J. W. F. Wasley, Synth. Commun., 13, 741 (1983).

    Google Scholar 

  84. K. Kondo and M. Matsumoto, Chem. Lett., No. 7, 701 (1974).

    Google Scholar 

  85. K. Kondo and M. Matsumoto, Jpn. Patent 7487657; Chem. Abstr., 82, 43168 (1975).

    Google Scholar 

  86. H. McNab and L. C. Monahan, J. Chem. Soc., Chem. Commun., No. 4, 213 (1985).

    Google Scholar 

  87. H. E. Simmons, R. D. Vest, S. A. Vladuchik, and O. W. Webster, J. Org. Chem., 45, 5113 (1980).

    Google Scholar 

  88. P. Nesvadba, Strop., and J. Kuthan, Coll., Czech. Chem. Commun., 48, 3307 (1983).

    Google Scholar 

  89. P. Nesvadba and J. Kuthan, Coll. Czech. Chem. Commun., 49, 543 (1984).

    Google Scholar 

  90. P. Nesvadba and J. Kuthan, Tetrahedron Lett., 21, 3727 (1980).

    Google Scholar 

  91. A. R. Katrizky, C. A. Ramsden, Z. Zaharia, R. L. Harlow, and S. H. Simonsen, J. Chem. Soc., Chem. Commun., No. 8, 363 (1979).

    Google Scholar 

  92. F. Bellamy, P. Martz, and J. Streith, Heterocycles, 3, 395 (1975).

    Google Scholar 

  93. S. I. Zav'yalov, I. F. Mustafaeva, and T. I. Skoblik, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2381 (1974).

    Google Scholar 

  94. K. M. Akhmedov, A. V. Kuchkarov, K. A. Akhmedov, and D. Yusupov, Khim. Geterotsikl. Soed., No. 2, 277 (1975).

    Google Scholar 

  95. R. S. Civens, D. J. Choo, N. N. Merchant, R. P. Stitt, and B. Matuszewski, Tetrahedron Lett., 23, 1327 (1982).

    Google Scholar 

  96. S. Nakanishi, Y. Shirai, K. Takahashi, and Y. Otsuji, Chem. Lett., No. 7, 869 (1981).

    Google Scholar 

  97. T. Tezuka, O. Seshimoto, and T. Mukai, Tetrahedron Lett., No. 13, 1067 (1975).

    Google Scholar 

  98. K. Ichimura, S. Ichikawa, and K. Imamura, Bull. Chem. Soc. Jpn., 49, 1157 (1976).

    Google Scholar 

  99. K. Ichimura, Jpn. Patent 7518462; Chem. Abstr., 83, 131448 (1975).

    Google Scholar 

  100. Y. Kawamatsu, H. Sugihara, and Y. Hamuro, Jpn. Patent 7416864; Chem. Abstr., 82, 125271 (1975).

    Google Scholar 

  101. R. K. Howe and L. F. Lee, Eur. Patent 88743; Chem. Abstr., 100, 6331 (1984).

    Google Scholar 

  102. S. Robev, Tetrahedron Lett., No. 13, 1163 (1978).

    Google Scholar 

  103. S. K. Robev, Dokl. Bolg. Akad. Nauk, 31, 197 (1978).

    Google Scholar 

  104. K. Gewald and U. Hain, Synthesis, No. 1, 62 (1984).

    Google Scholar 

  105. F. Bellamy, J. L. Schuppiser, and Y. Streith, Heterocycles, No. 11, Spec. Issue, 461 (1978).

    Google Scholar 

  106. L. S. Stanishevskii, I. G. Tishchenko, and V. I. Tyvorskii, Izv. Akad. Nauk BSSR, Ser. Khim. Nauk, No. 1, 104 (1977).

    Google Scholar 

  107. L. N. Shil'nikova and F. Ya. Perveev, Zh. Org. Khim., 14, 251 (1978).

    Google Scholar 

  108. M. Komatsu, Y. Yoshida, M. Uesaka, Y. Ohshiro, and T. Agawa, J. Org. Chem., 49, 1300 (1984).

    Google Scholar 

  109. B. A. Trofimov and A. I. Mikhaleva, Khim. Geterotsikl. Soed., No. 10, 1299 (1987).

    Google Scholar 

  110. A. Padwa, Angew. Chem., Int. Ed. Engl., 15, No. 3, 123 (1976).

    Google Scholar 

  111. P. Faria Dos Santos Filho and U. Schuchardt, Angew. Chem., 89, 672 (1977).

    Google Scholar 

  112. F. D. Bellamy, Tetrahedron Lett., No. 46, 4577 (1978).

    Google Scholar 

  113. A. Laurent, P. Mison, A. Nafti, and N. Pellissier, Tetrahedron, 35, 2285 (1979).

    Google Scholar 

  114. A. Hassner, Heterocycles, 14, 1517 (1980).

    Google Scholar 

  115. P. DeShong, D. A. Kell, and D. R. Sidler, J. Org. Chem., 50, 2309 (1985).

    Google Scholar 

  116. L. Vo-Quang and Y. Vo-Quang, Tetrahedron Lett., 47, 4679 (1978).

    Google Scholar 

  117. L. Vo-Quang and Y. Vo-Quang, J. Heterocycl. Chem., 19, 145 (1982).

    Google Scholar 

  118. B. Merah and E. Texier, Bull. Soc. Chim. France, 11–12, 552 (1980).

    Google Scholar 

  119. N. De Kimpe, P. Sulmon, L. De Buyok, R. Vehre, N. Schamp, J. P. Declereg, and M. Van Meerssche, J. Chem. Res. Synop., No. 3, 82 (1984).

    Google Scholar 

  120. V. Reutrakul, V. Prapansiri, and C. Panyachotipun, Tetrahedron Lett., 25, 1949 (1984).

    Google Scholar 

  121. C. Mahidol, V. Reutrakul, V. Prapansiri, and C. Panyachotipun, Chem. Lett., No. 6, 969 (1984).

    Google Scholar 

  122. J. Leroy, M. Rubinstein, and C. Wakselman, J. Fluorine Chem., 25, 255 (1984).

    Google Scholar 

  123. J. Leroy and C. Wakselman, Can. J. Chem., 54, 218 (1976).

    Google Scholar 

  124. A. Padwa, D. Dean, A. Mazzu, and E. Vega, J. Am. Chem. Soc., 95, 7168 (1973).

    Google Scholar 

  125. G. L'Abbe, L. Huybrechts, and S. Topper, Bull. Soc. Chim. Belges, 87, 893 (1978).

    Google Scholar 

  126. J. S. Davies, Tetrahedron Lett., 23, 5089 (1982).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 291–308, March, 1989.

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Sobenina, L.N., Mikhaleva, A.I. & Trofimov, B.A. Synthesis of pyrroles from heterocyclic compounds (review). Chem Heterocycl Compd 25, 237–253 (1989). https://doi.org/10.1007/BF00472377

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