Skip to main content
Log in

Functionalization of pyridines. 3. Reactions forming a carbon-heteroatom bond with group IV, V, and VI elements

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The literature from the last 15–20 years on the synthesis of heteroatomic pyridine derivatives through the formation of pyridine carbon-heteroatom bonds is reviewed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. M. A. Yurovskaya, O. D. Mit'kin, and F. V. Zaitseva,Khim. Geterotsikl. Soedin., No. 8, 1013 (1998).

    Google Scholar 

  2. S. L. Taylor, D. Y. Lee, and J. C. Martin,J. Org. Chem.,48, 4156 (1983).

    CAS  Google Scholar 

  3. D. Comis and N. B. Mantlo,Tetrahedron Lett.,24, 3683 (1983).

    Google Scholar 

  4. Y. Hamamoto and A. Yanagi,Heterocycles,19, 41 (1982).

    Google Scholar 

  5. Y. Yamamoto and A. Yanagi,Chem. Pharm. Bull.,30, 2003 (1982).

    CAS  Google Scholar 

  6. Y. Yamamoto, T. Tanaka, H. Ouchi, M. Miyakawa, and Y. Morita,Heterocycles,41, 817 (1995).

    CAS  Google Scholar 

  7. E. Ya. Lukevics and I. D. Segal, Preprint. Parts 1 (63 pp.) and 2 (70 pp.), Institute of Organic Synthesis, Latvian SSR Academy of Sciences, Riga (1986).

  8. E. Ya. Lukevics and I.D. Segal,Khim. Geterotsikl. Soedin., No. 1, 5 (1987).

    Google Scholar 

  9. E. Lukevics and I. D. Segal, in:Organic Chemistry Reviews, G. Davies et al. (eds.), J. Organomet. Chem. Library, Vol. 20, Elsevier, Amsterdam etc. (1988), p. 69.

    Google Scholar 

  10. J. Verbeek, A. V. E. George, R. L. P. De Jong, and L. V. Brandsma,J. Chem. Soc., Chem. Commun., No. 4, 257 (1984).

    Google Scholar 

  11. A. G. M. Barrett, D. Dauzonne, I. A. O'Neil, and A. Renaud,J. Org. Chem.,49, 4409 (1984).

    Article  Google Scholar 

  12. F. Marsais, F. Trecourt, P. Breant, and G. Queguiner,J. Heterocycl. Chem.,25, 81 (1988).

    CAS  Google Scholar 

  13. D. Comis and Y. Ch. Myoung,J. Org. Chem.,55, 292 (1990).

    Google Scholar 

  14. M. Zeldin and J.-M. Xu,J. Organomet. Chem.,320, 267 (1987).

    Article  CAS  Google Scholar 

  15. F. Trecourt, M. Mallet, F. Marsais, and G. Queguiner,J. Org. Chem.,53, 1367 (1988).

    Article  CAS  Google Scholar 

  16. N. Furakawa, T. Shibutani, and H. Fujihara,Tetrahedron Lett.,30, 7091 (1989).

    Google Scholar 

  17. C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, and V. Snieckus,Tetrahedron Lett.,33, 2625 (1992).

    Article  CAS  Google Scholar 

  18. A. R. Katritzky, J. M. Aurrecoechea, and L. M. Vazquez de Miguel,Heterocycles,26, 427 (1987).

    CAS  Google Scholar 

  19. M. Tsukazaki and V. Snieckus,Heterocycles,35, 689 (1993).

    CAS  Google Scholar 

  20. S. G. Davies and M. R. Shipton,J. Chem. Soc. Perkin Trans. 1, No. 3, 501 (1991).

    Google Scholar 

  21. S. G. Ang and W. L. Kwik,J. Organomet. Chem.,361, 27 (1989).

    Article  CAS  Google Scholar 

  22. P. Jutzi and U. Gilge,J. Organomet. Chem.,246, 163 (1983).

    CAS  Google Scholar 

  23. A. Shih-Yuan and W.-C. Dai,Tetrahedron Lett.,37, 495 (1996).

    Google Scholar 

  24. Y. Yamamoto and A. Yanagi,Heterocycles,16, 1161 (1981).

    CAS  Google Scholar 

  25. F. Friedel,Ber.,45, 428 (1912).

    Google Scholar 

  26. H. Suzuki, T. Murashima, and K. Tsukamoto, Jpn. Pat. 04282368;Chem. Abstr.,108, 101821 (1988).

    Google Scholar 

  27. H. Suzuki, I. Kozai, and T. Murashima,J. Chem. Res., Synop., No. 4, 156 (1993).

    Google Scholar 

  28. H. Suzuki, M. Iwaya, and T. Mori,Tetrahedron Lett.,38, 5647 (1997).

    CAS  Google Scholar 

  29. J. M. Bakke, I. Hegbom, E. Overleide, and K. Aaby,Acta Chem. Scand.,48, 1001 (1994).

    CAS  Google Scholar 

  30. J. M. Bakke and E. Rames,Synthesis, No. 3, 281 (1997).

    Google Scholar 

  31. J. M. Bakke, E. Ranes, J. Rina, and H. Svensen, in:Abstracts of the 7th Blue Danube Symposium on Heterocyclic Chemistry, Eger, Hungary (1998), PO7.

  32. W. Orth and W. Fickert, Ger. Offen. Pat. 3308449;Chem. Abstr.,101, 23354 (1984).

    Google Scholar 

  33. T. Clausen and E. Konrad, Ger. Offen. Pat. 3706565;Chem. Abstr.,110, 13383 (1989).

    Google Scholar 

  34. H. Ritter and H. H. Licht,J. Heterocycl. Chem.,32, 585 (1995).

    CAS  Google Scholar 

  35. J. Loreno and Z. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,313, 131 (1985);Chem. Abstr.,107, 84354 (1986).

    CAS  Google Scholar 

  36. T. Talik and Z. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,313, 121 (1985);Chem. Abstr.,106, 84353 (1987).

    CAS  Google Scholar 

  37. M. Wandas and T. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,435, 129 (1988);Chem. Abstr.,112, 178598 (1990).

    CAS  Google Scholar 

  38. B. Palasek and T. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,435, 119 (1988);Chem. Abstr.,112, 178597 (1990).

    CAS  Google Scholar 

  39. I. F. Falyakhov, R. Z. Gil'manov, G. P. Sharnin, and T. G. Bol'shakova,Khim. Geterotsikl. Soedin., No. 7, 958 (1998).

    Google Scholar 

  40. T. Talik and Z. Talik,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,313, 115 (1985);Chem. Abstr.,106, 82352 (1987).

    CAS  Google Scholar 

  41. A. Puszko,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,278, 169 (1984);Chem. Abstr.,103, 104819 (1985).

    CAS  Google Scholar 

  42. A. N. Osman and M. Khalifa,Egypt. J. Chem.,27, 705 (1985).

    CAS  Google Scholar 

  43. W. Hallenbach and H. Lindel, Ger. Offen. Pat. 3707361;Chem. Abstr.,113, 38900 (1990).

    Google Scholar 

  44. A. A. Nazibulin and M. V. Klyuev,Zh. Org. Khim.,31, 1068 (1995).

    Google Scholar 

  45. M. Malinowski and I. Kaczmarek, Pol. Pat. 149751;Chem. Abstr.,113, 230409 (1990).

    Google Scholar 

  46. M. Malinowski,Bull. Soc. Chim. Belg.,97, 51 (1988).

    CAS  Google Scholar 

  47. G. L. Rusinov, I. E. Filatov, and K. I. Pashkevich,Izv. Ross. Akad. Nauk, Ser. Khim., No. 2, 365 (1993).

    Google Scholar 

  48. L. Kaczmarek, R. Balicki, and M. Malinowski,J. Prakt. Chem.,332, 423 (1990).

    Article  CAS  Google Scholar 

  49. C. K. McGill and J. J. Sutor, U.S. Pat. 4386209;Chem. Abstr.,100, 6343 (1984).

    Google Scholar 

  50. Reilly Tar and Chem. Corp., Jpn. Pat. 58208266;Chem. Abstr.,100, 120901 (1984).

    Google Scholar 

  51. C. K. McGill and T. D. Bailey, U.S. Pat. 4405790;Chem. Abstr.,100, 22584 (1984).

    Google Scholar 

  52. S. Enomoto and H. Kashiwagi, Jpn. Rat. 7995576;Chem. Abstr.,92, 6424 (1980).

    Google Scholar 

  53. H. Kashiwagi and S. Enomoto,Yakugaku Zasshi,100, 140 (1980);Chem. Abstr.,93, 25483 (1980).

    CAS  Google Scholar 

  54. D. J. Buurman and H. C. van der Plas,J. Heterocycl. Chem.,23, 1015 (1986).

    CAS  Google Scholar 

  55. R. A. Hollins, L. H. Merwin, R. A. Nissan, W. S. Wilson, and R. Gilardi,J. Heterocycl. Chem.,33, 895 (1996).

    Google Scholar 

  56. F. E. Janssens, G. S. M. Diels, J. L. G. Torremans, and F. M. Sommen, Eur. Pat. 282133;Chem. Abstr.,110, 75503 (1989).

    Google Scholar 

  57. A.-G. Degussa, Belg. Pat. 890331;Chem. Abstr.,97, 6159 (1982).

    Google Scholar 

  58. Koei Kagaku Kogyo K. K., Jpn. Pat. 8265756;Chem. Abstr.,97, 111294 (1982).

    Google Scholar 

  59. P. C. Jain and N. Anand, Ind. Pat. 101837;Chem. Abstr.,92, 76552 (1979).

    Google Scholar 

  60. W. G. Lobeck, Jr., J. S. New, and J. P. Yevich, Ger. Offen. Pat. 3601143;Chem. Abstr.,105, 172510 (1986).

    Google Scholar 

  61. K. Matsumoto, H. Minatogawa, M. Munakata, M. Toda, and H. Tsukube,Tetrahedron Lett.,31, 3923 (1990).

    CAS  Google Scholar 

  62. A. M. Sipyagin and V. G. Kartsev,Zh. Org. Khim.,23, 2187 (1987).

    CAS  Google Scholar 

  63. V. Hagen, A. Hagen, S. Heer, R. Mitzner, and H. Niedrich,Pharmazie,44, 20 (1989).

    CAS  Google Scholar 

  64. M. A. Hassan, E. A. Soliman, and A. A. Hamed,Rev. Roum. Chim.,27, 963 (1982);Chem. Abstr.,98, 89133 (1983).

    CAS  Google Scholar 

  65. A. R. Katritzky, S. Rachwal, T. P. Smith, and P. J. Steel,J. Heterocycl. Chem.,32, 179 (1995).

    Google Scholar 

  66. P. Bamfield, E. D. Harvey, and N. Hughes, G. Brit. Pat. 2144740;Chem. Abstr.,104, 34009 (1986).

    Google Scholar 

  67. I. Yokomichi, T. Haga, K. Nagatani, and T. Nakajima, U.S. Pat. 4349681;Chem. Abstr.,97, 216025 (1982).

    Google Scholar 

  68. T. Haga, K. Fujikawa, T. Koyanagi, T. Nakajima, and K. Hayashi,Heterocycles,22, 117 (1984).

    CAS  Google Scholar 

  69. T. R. Perrior, A. J. Whittle, and D. J. Tapolczay, Eur. Pat. 357201;Chem. Abstr.,113, 172036 (1990).

    Google Scholar 

  70. N. Matsuo, H. Takeda, T. Yano, S. Nishida, and K. Tsushima, Jpn. Pat. 6172754;Chem. Abstr.,105, 97337 (1986).

    Google Scholar 

  71. K. Matsumoto, T. Uryu, and M. Munakata,Chem. Express,3, 739 (1988).

    CAS  Google Scholar 

  72. E. Hang and D. C. Baker,Synthesis, No. 12, 905 (1989).

    Google Scholar 

  73. M. Mamaghani and R. E. Banks,J. Sci. Islamic Repub. Iran,5, 98 (1994);Chem. Abstr.,123, 285715 (1995).

    CAS  Google Scholar 

  74. W. S. Saari, U.S. Pat. 4456604;Chem. Abstr.,101, 130718 (1984).

    Google Scholar 

  75. W. S. Saari, U.S. Pat. 4442103;Chem. Abstr.,101, 60140 (1984).

    Google Scholar 

  76. N. Kaishi, K. Araki, and S. Shiraishi,Bull. Chem. Soc. Jpn.,57, 2121 (1984).

    Google Scholar 

  77. L. M. Litvinenko, G. D. Titskii, and E. S. Mitchenko,Zh. Org. Khim.,19, 1970 (1983).

    CAS  Google Scholar 

  78. L. M. Litvinenko, G. D. Titskii, and E. S. Mitchenko,Zh. Org. Khim.,20, 1704 (1984).

    CAS  Google Scholar 

  79. G. D. Titskii and E. S. Mitchenko,Zh. Org. Khim.,24, 2161 (1988).

    CAS  Google Scholar 

  80. M. Sammes, K. W. Ho, M. Tam, and A. R. Katritzky,J. Chem. Soc., Perkin Trans 1, No. 5, 973 (1983).

    Google Scholar 

  81. D. A. De Bie, B. Geurtsen, and H. C. van der Plas,J. Org. Chem.,50, 484 (1985).

    Google Scholar 

  82. D. A. De Bie, B. Geurtsen, I. E. Berg, and H. C. van der Plas,J. Org. Chem.,51, 3209 (1986).

    Google Scholar 

  83. J. W. Streef, H. J. den Hertog, and H. C. van der Plas,J. Heterocycl. Chem.,22, 985 (1985).

    CAS  Google Scholar 

  84. R. J. Ife, Eur. Pat. 113572;Chem. Abstr.,102, 6529 (1985).

    Google Scholar 

  85. Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60112768;Chem. Abstr.,103, 215186 (1985).

    Google Scholar 

  86. Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60112769;Chem. Abstr.,103, 215187 (1985).

    Google Scholar 

  87. D. Nisato and P. Carminati, Fr. Pat. 2467849;Chem. Abstr.,96, 35101 (1982).

    Google Scholar 

  88. A. Gilbert and S. Krestonosich,J. Chem. Soc., Perkin Trans. 1, No. 11, 2531 (1980).

    Google Scholar 

  89. Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60113762;Chem. Abstr.,102, 220761 (1985).

    Google Scholar 

  90. G. Scheffler, J. Engel, V. Jakovlev, B. Nickel, and K. Thiemer, Eur. Pat. 149088;Chem. Abstr.,103, 215189 (1985).

    Google Scholar 

  91. Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60112767;Chem. Abstr.,103, 196012 (1985).

    Google Scholar 

  92. Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 60137631;Chem. Abstr.,102, 220760 (1985).

    Google Scholar 

  93. K. Tsuzuki, T. Uotani, and M. Hashihama, Jpn. Pat. 60169463;Chem. Abstr.,104, 50798] (1986).

    Google Scholar 

  94. Toyo Soda Mfg. Co., Ltd., Jpn. Pat. 59122468;Chem. Abstr.,102, 6214 (1985).

    Google Scholar 

  95. P. E. Cross and R. P. Dickinson, Eur. Pat. 291210;Chem. Abstr.,110, 154160 (1989).

    Google Scholar 

  96. K. Samula and B. Rostafinska,Pol. Chem. J.,55, 1667 (1981).

    CAS  Google Scholar 

  97. A. Greiner,Synthesis, No. 4, 312 (1989).

    Google Scholar 

  98. S. Cacchi, A. Carangio, G. Fabrizi, L. Moro, and P. Pace,Synlett, No. 12, 1400 (1997).

    Google Scholar 

  99. H. Haeuser and G. Walter, Ger. Offen. Pat. 3241429;Chem. Abstr.,101, 72621 (1984).

    Google Scholar 

  100. J. M. Greene, A. J. Pike, E. R. Lavagnino, and E. C. Taylor, Eur. Pat. 149537;Chem. Abstr.,103, 215190 (1985).

    Google Scholar 

  101. R. Bernardi, T. Caronna, S. Morrocchi, M. Ursini, and B. M. Vittimberga,J. Chem. Soc., Perkin Trans. 1, No. 1, 97 (1990).

    Google Scholar 

  102. A. S. Kiselyov and L. Strekowski,Synth. Commun.,24, 2387 (1994).

    CAS  Google Scholar 

  103. K. Yamauchi, K. Nakao, F. Nishimura, and K. Tamaoki, Jpn. Pat. 0138072;Chem. Abstr.,111, 57552 (1989).

    Google Scholar 

  104. B. Narasaiah, A. Sivaprasad, and R. V. Venkataratnan,J. Fluorine Chem.,67, 87 (1994).

    Google Scholar 

  105. D. Quarroz, Eur. Pat. 90173;Chem. Abstr.,100, 68178 (1984).

    Google Scholar 

  106. Yu. V. Kurbatov and M. A. Solekhova,Zh. Org. Khim.,19, 663 (1983).

    CAS  Google Scholar 

  107. Yu. V. Kurbatov and M. A. Solekhova,Khim. Geterotsikl. Soedin., No. 7, 936 (1986).

    Google Scholar 

  108. E. B. Lifshits, Yu. M. Karpova, and M. N. Ushomirskii,Khim. Geterotsikl. Soedin., No. 9, 1278 (1989).

    Google Scholar 

  109. T. Hisano, T. Matsuoka, M. Ichikawa, and M. Hamana,Heterocycles,14, 19 (1980).

    CAS  Google Scholar 

  110. R. A. Abramovitch, J. Pilski, A. Konitz, and P. Tomasik,J. Org. Chem.,48, 4391 (1983).

    CAS  Google Scholar 

  111. W. Czuba and J. Wodzinska,Pol. J. Chem.,68, 1343 (1994).

    CAS  Google Scholar 

  112. Y. Tamura, M. Fujita, C. L. Ching, H. Kiyokawa, K. Ueno, and Y. Kita,Heterocycles,15, 871 (1981).

    CAS  Google Scholar 

  113. J. B. Campbell, E. R. Lavagnino, and A. J. Pike, Eur. Pat. 159112;Chem. Abstr.,104, 148751 (1986).

    Google Scholar 

  114. N. Ple and G. Queguiner,J. Heterocycl. Chem.,26, 475 (1989).

    CAS  Google Scholar 

  115. B. R. Eric, W. J. Jondi, and A. E. Tipping,J. Fluorine Chem.,77, 87 (1996).

    Google Scholar 

  116. V. G. Kartsev, E. M. Gizatullina, and Z. G. Aliev,Khim. Geterotsikl. Soedin., No. 3, 369 (1992).

    Google Scholar 

  117. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 58213776;Chem. Abstr.,100, 209853 (1984).

    Google Scholar 

  118. L. R. Hatton, E. W. Parnell, and D. A. Roberts, Ger. Offen. Pat. 3408727;Chem. Abstr.,102, 45922 (1985).

    Google Scholar 

  119. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 58198469;Chem. Abstr.,100, 156508 (1984).

    Google Scholar 

  120. A. M. Sipygin and Z. G. Aliev,Khim. Geterotsikl. Soedin., No. 11, 1495 (1993).

    Google Scholar 

  121. T. Talik, J. Lorenc, and M. Pupin,Pr. Nauk Akad. Ekon. im. Oskara Langego Wroclawiu,255, 131 (1984).

    CAS  Google Scholar 

  122. L. Davis, G. E. Olsen, J. T. Klein, K. J. Kapples, F. P. Huger, C. P. Smith, W. W. Petko, M. Confoldt, and R. C. Effland,J. Med. Chem.,39, 582 (1996).

    Google Scholar 

  123. J. B. Campbell, J. M. Greene, E. R. Lavagnino, D. N. Gardner, A. J. Pike, J. Snoddy, and E. C. Taylor,J. Heterocycl. Chem.,23, 669 (1986).

    CAS  Google Scholar 

  124. N. R. Ayyangar, S. Madan Kumar, and K. V. Srinivasan,Synthesis, No. 7, 616 (1987).

    Google Scholar 

  125. H. A. Al-Lohedan,Tetrahedron,46, 3593 (1990).

    CAS  Google Scholar 

  126. R. B. Rogers, B. C. Gerwick, and E. A. Egli, U.S. Pat. 4474599;Chem. Abstr.,102, 45956 (1985).

    Google Scholar 

  127. A. A. Tolmachev and E. S. Kozlov,Khim. Geterotsikl. Soedin., No. 12, 1587 (1986).

    Google Scholar 

  128. Wenhao Hu, C. C. Pai, C. C. Chen, Guopin Xue, and A. S. C. Chan,Tetrahedron: Asymmetry,9, 3241 (1998).

    Article  CAS  Google Scholar 

  129. Ya. A. Dofman and L. V. Levina,Khim. Geterotsikl. Soedin, No. 1, 128 (1992).

    Google Scholar 

  130. E. Anders and F. Markus,Tetrahedron Lett.,28, 2675 (1987).

    Article  CAS  Google Scholar 

  131. E. Anders and F. Markus,Chem. Ber.,120, 2675 (1987).

    Google Scholar 

  132. D. Fukuoka, K. Takahashi, and I. Hashimoto, Ch. Pat. 88100659;Chem Abstr.,110, 173099 (1989).

    Google Scholar 

  133. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 81123970;Chem. Abstr.,96, 6602 (1982).

    Google Scholar 

  134. V. M. Petrichenko and M. E. Konshin, in:Synthetic Methods of Basic Hetero-Organic Compounds [in Russian], I. I. Lapkin (ed.), Perm State Univ., Perm (1982), p. 69.

    Google Scholar 

  135. R. Nishiyama, K. Fujikawa, T. Haga, T. Toki, T. Komoyoji, N. Sakashita, and K. Maeda, Can. Pat. 1176637;Chem. Abstr., 102, 149119 (1985).

    Google Scholar 

  136. M. Boger and J. Ehrenfreund, Eur. Pat. 40179;Chem. Abstr.,96, 85429 (1982).

    Google Scholar 

  137. H. Rempfler, R. Schurter, and W. Foery, U.S. Pat. 4325729;Chem. Abstr.,97, 23638 (1982).

    Google Scholar 

  138. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 57145861;Chem. Abstr.,98, 71950 (1983).

    Google Scholar 

  139. T. P. Selby, Eur. Pat. 61913;Chem. Abstr.,98, 71949 (1983).

    Google Scholar 

  140. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 82102865;Chem. Abstr.,97, 182218 (1982).

    Google Scholar 

  141. H. Rempfler and B. Bohner, Eur. Pat. 50097;Chem. Abstr.,97, 144777 (1982).

    Google Scholar 

  142. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 8277674;Chem. Abstr.,97, 127508 (1982).

    Google Scholar 

  143. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 57109768;Chem. Abstr.,98, 89175 (1983).

    Google Scholar 

  144. R. C. Krauss, Eur. Pat. 66827;Chem. Abstr.,98, 198027 (1983).

    Google Scholar 

  145. R. C. Krauss, U.S. Pat. 4410701;Chem. Abstr.,100, 34417 (1984).

    Google Scholar 

  146. R. Kirsten, R. Andree, U. Busse, A. Marhold, H. J. Santel, R. R. Schmidt, K. Luerssen, and H. Strang, Ger. Offen. Pat. 3729071;Chem. Abstr.,109, 149365 (1988).

    Google Scholar 

  147. T. J. Adaway, Eur. Pat. 128658;Chem. Abstr.,102, 166617 (1985).

    Google Scholar 

  148. P. A. Cain, U.S. Pat. 4521425;Chem. Abstr.,103, 160402 (1985).

    Google Scholar 

  149. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 60112765;Chem. Abstr.,104, 5792 (1986).

    Google Scholar 

  150. T. Oe, Y. Ono, K. Kawasaki, and T. Nakajima, Eur. Pat. 359547;Chem. Abstr.,113, 115095 (1982).

    Google Scholar 

  151. R. Becker, W. Hoffmann, H. G. Oeser, W. Rohr, and J. Varwig, Ger. Offen. Pat. 3151589;Chem. Abstr.,100, 103180 (1984).

    Google Scholar 

  152. R. Schurter, U. Siegrist, H. Rempfler, and P. Baumeister, Eur. Pat. 178260;Chem. Abstr.,105, 97327 (1986).

    Google Scholar 

  153. R. L. Burson, Eur. Pat. 136593;Chem. Abstr.,103, 104856 (1985).

    Google Scholar 

  154. H. Johnston, U.S. Pat. 4360524;Chem. Abstr.,98, 125892 (1983).

    Google Scholar 

  155. L. D. Markley, Y. C. Tong, J. K. Dulworth, D. L. Steward, C. T. Goralski, H. Johnston, S. G. Wood, A. P. Vinogradoff, and T. M. Bargar,J. Med. Chem.,29, 427 (1986).

    Article  CAS  Google Scholar 

  156. S. L. Pendalwar, D. T. Chaudhari, and M. R. Patel,Bull. Haffkine Inst.,8, 33 (1980);Chem. Abstr.,97, 55722 (1982).

    CAS  Google Scholar 

  157. J. J. Baldwin and G. S. Ponticello, U.S. Pat. 4329351;Chem. Abstr.,97, 72256 (1982).

    Google Scholar 

  158. J. Macor and M. Newman,Heterocycles,31, 805 (1990).

    CAS  Google Scholar 

  159. L. Schroeder, R. Mengel, W. Stransky, G. Linden, and S. Lust, Ger. Offen. Pat. 3242519;Chem. Abstr.,101, 90778 (1984).

    Google Scholar 

  160. K. J. Hwang and S. K. Park,Synth. Commun.,20, 949 (1990).

    CAS  Google Scholar 

  161. T. Kagawa, T. Uotani, and K. Tsuzuki, Jpn. Pat. 01153677;Chem. Abstr.,111, 173997 (1989).

    Google Scholar 

  162. Seitetsu Kagaku Co., Ltd., Jpn. Pat. 58154561;Chem. Abstr.,100, 120891 (1984).

    Google Scholar 

  163. P. Ballesteros, R. M. Claramunt, and J. Elguero,Tetrahedron,43, 2557 (1987).

    Article  CAS  Google Scholar 

  164. M. I. Attalla, G. R. Burnett, and L. A. Summers,J. Heterocycl. Chem.,22, 319 (1985).

    CAS  Google Scholar 

  165. R. S. Dainter, H. Suschitzky, B. J. Wakefield, M. Hughes, and J. Nelson,Tetrahedron Lett.,25, 5693 (1984).

    Article  CAS  Google Scholar 

  166. S. K. Kotovskaya, G. A. Mokrushina, and I. Ya. Postovskii,Khim. Geterotsikl. Soedin., No. 3, 373 (1983).

    Google Scholar 

  167. K. Rajyalakshmi and V. R. Srinivasan,Indian J. Chem., Sect. B,18, 226 (1979).

    Google Scholar 

  168. R. S. Dainer, L. Julia, H. Suschitzky, and B. J. Wakefield,J. Chem. Soc., Perkin Trans. 1, No. 12, 2897 (1982).

    Google Scholar 

  169. R. E. Banks, W. Jondi, and A. E. Tipping,J. Chem. Soc., Chem. Commun., No. 17, 1268 (1989).

    Google Scholar 

  170. A. Nahara and Y. Maki, Eur. Pat. 174726;Chem. Abstr., 105, 133883 (1986).

    Google Scholar 

  171. L. Eggers and W. Grahn,Synthesis, No. 6, 763 (1996).

    Google Scholar 

  172. T. Talik and Z. Talik,Pr. Nauk. Akad. Ekon. im. Oskara Langego Wroclawiu,278, 163 (1984);Chem. Abstr.,103, 104818 (1985).

    CAS  Google Scholar 

  173. T. Fujii, T. Hiraga, and M. Ohba,Chem. Pharm. Bull.,29, 2503 (1981).

    CAS  Google Scholar 

  174. A. R. Katritzky, R. C. Patel, and M. Shanta,J. Chem. Soc., Perkin Trans. 1, No. 9, 1888 (1980).

    Google Scholar 

  175. P. Tomasik, A. Woszczyk, R. A. Abramovitch,J. Heterocycl. Chem.,16, 1283 (1979).

    CAS  Google Scholar 

  176. T. Umemoto and G. Tomizawa,Tetrahedron Lett.,28, 2705 (1987).

    Article  CAS  Google Scholar 

  177. S. Rosen, D. Hebel, and D. Zamiz,J. Am. Chem. Soc.,109, 3789 (1987).

    Google Scholar 

  178. S. Rosen and D. Hebel,Heterocycles,28, 249 (1989).

    Google Scholar 

  179. D. Hebel and S. Rosen,J. Org. Chem.,53, 1123 (1988).

    Article  CAS  Google Scholar 

  180. M. Ueki, M. Honda, Y. Kazama, and T. Katoh,Synthesis, No. 1, 21 (1994).

    Google Scholar 

  181. C. O. Okafor,J. Org. Chem.,47, 592 (1982).

    Article  CAS  Google Scholar 

  182. Z. Weglinski,Pr. Nauk. Akad. Ekon. im. Oskara Langego Wroclawiu,435, 149 (1988);Chem. Abstr.,112, 76911 (1990).

    CAS  Google Scholar 

  183. J. Becher and J. Lundsgaard,Phosphorus Sulfur Relat. Elem.,14, 131 (1983).

    CAS  Google Scholar 

  184. J. Becher and J. Lundsgaard,Sulfur Lett.,1, 5 (1982).

    CAS  Google Scholar 

  185. J. M. Teulon, Eur. Pat. 162776;Chem. Abstr.,104, 109668 (1986).

    Google Scholar 

  186. V. N. Knyazev, V. N. Drozd, and T. Ya. Mozhaeva,Izv. Timiryazevsk. S-kh. Akad., No. 1, 182 (1983).

    Google Scholar 

  187. R. G. Suhr and J. L. Miesel, U.S. Pat. 4264605;Chem. Abstr.,96, 52182 (1982).

    Google Scholar 

  188. C. T. Redemann, U.S. Pat. 4490380;Chem. Abstr.,102, 166625 (1985).

    Google Scholar 

  189. M. Ueki and T. Watanabe, Jpn. Pat. 06228098;Chem. Abstr.,121, 300773 (1994).

    Google Scholar 

  190. W. W. Brand and J. M. Gullo, Eur. Pat. 36638;Chem. Abstr.,96, 142709 (1982).

    Google Scholar 

  191. K. C. Pugh, L. Gera, and J. M. Stewart,Peptide Chemistry 1992, Proc. Jpn. Symp. 2nd 1992, (1993), p. 37;Chem. Abstr.,121, 9114 (1994).

    Google Scholar 

  192. K. A. Memoli,Tetrahedron Lett.,37, 3617 (1996).

    Google Scholar 

  193. S. V. Amosova, V. I. Gostevskaya, G. M. Gavrilova, and A. V. Afonin,Zh. Org. Khim.,29, 1501 (1993).

    CAS  Google Scholar 

  194. Yu. C. Tong, U.S. Pat. 4558134;Chem. Abstr.,105, 6409 (1986).

    Google Scholar 

  195. S. Kondo, M. Nakanishi, and K. Tsuba,J. Heterocycl. Chem.,21, 1243 (1984).

    CAS  Google Scholar 

  196. R. Beugelmans, M. Bois-Choussy, and B. Boudet,Tetrahedron,39, 4153 (1983).

    Article  CAS  Google Scholar 

  197. L. Testaferri, M. Tiecco, M. Tingoli, D. Chianelli, and M. Montanucci,Synthesis, No. 9, 751 (1983).

    Google Scholar 

  198. B. Boduszek and J. S. Wieczorek,Monatsh. Chem.,111, 1111 (1980).

    CAS  Google Scholar 

  199. A. M. Sipyagin, S. V. Pal'tsun, I. A. Pomytkin, and N. N. Aleinikov,Khim. Geterotsikl. Soedin., No. 1, 63 (1994).

    Google Scholar 

  200. N. K. Goswami,Indian J. Chem., Sect. B,21, 364 (1983).

    Google Scholar 

  201. S. G. Woods, B. T. Matyas, A. P. Vinogradoff, and Y. C. Tong,J. Heterocycl. Chem.,21, 97 (1984).

    CAS  Google Scholar 

  202. L. Testaferri, M. Tiecco, M. Tigoli, D. Bartoli, and A. Massoli,Tetrahedron,41, 1373 (1985).

    CAS  Google Scholar 

  203. N. Furukawa, S. Ogawa, T. Kawai, and S. Oae,Tetrahedron Lett.,24, 3243 (1983).

    CAS  Google Scholar 

  204. N. Furukawa, S. Ogawa, T. Kawai, and S. Oae,J. Chem. Soc., Perkin Trans. 1, No. 8, 1839 (1984).

    Google Scholar 

  205. C. Bieniarz and M. J. Cornwell,Tetrahedron Lett.,34, 939 (1993).

    Article  CAS  Google Scholar 

  206. Ishihara Sangyo Kaisha Ltd., Jpn. Pat. 58170759;Chem. Abstr.,100, 209626 (1984).

    Google Scholar 

  207. A. M. Sipyagin and Z. G. Aliev,Khim. Geterotsikl. Soedin., No. 9, 1207 (1993).

    Google Scholar 

  208. A. Couture, P. Grandclaudon, and E. Huguerre,J. Heterocycl. Chem.,24, 1765 (1987).

    CAS  Google Scholar 

  209. J. B. Adams, Jr., U.S. Pat. 4456469;Chem. Abstr.,101, 191972 (1984).

    Google Scholar 

  210. M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli, D. Bartoli, and R. Balducci,Tetrahedron,44, 4883 (1988).

    CAS  Google Scholar 

  211. L. Syper and J. Mtochowski,Tetrahedron 44, 6119 (1988).

    Article  CAS  Google Scholar 

  212. K. Smith, I. Mattheurs, and G. E. Martin,J. Chem. Soc., Perkin Trans. 1, No. 12, 2839 (1987).

    Google Scholar 

  213. J. Chen and G. T. Crisp,Synth. Commun.,22, 683 (1992).

    CAS  Google Scholar 

  214. H. J. Cristau, B. Chaband, R. Labandiniere, and H. Christol,Organometallics,4, 657 (1985).

    Article  CAS  Google Scholar 

  215. Z. C. Chang, Q. Jiang, B. X. Xu, S. Z. Tu, Z. Y. Ma, P. Zhu, and Q. H. Yang,Yaoxue Xuebao,30, 263 (1995);Chem. Abstr.,123, 55666 (1995).

    CAS  Google Scholar 

  216. H. Ban-Oganowska,Chem. Pap.,49, 94 (1995);Chem. Abstr.,124, 55759 (1996).

    CAS  Google Scholar 

  217. A. M. Sipyagin, V. V. Kolchanov, and S. V. Pal'tsun,Khim. Geterotsikl. Soedin., No. 9, 1216 (1993).

    Google Scholar 

  218. A. M. Sipyagin, V. V. Kolchanov, and N. N. Sveshnikov,Tetrahedron Lett.,35, 3147 (1994).

    Article  CAS  Google Scholar 

  219. L. Bauer and S. Prachayasittikul,Heterocycles,24, 161 (1986).

    CAS  Google Scholar 

  220. N. Sato and E. Nagano,J. Heterocycl. Chem.,30, 691 (1993).

    CAS  Google Scholar 

  221. Yoshitomi Pharmaceutical Industries, Ltd., Jpn. Pat. 5888362;Chem. Abstr.,99, 122318 (1983).

    Google Scholar 

  222. Yoshitomi Pharmaceutical Industries, Ltd., Jpn. Pat. 58152867;Chem. Abstr.,100, 103181 (1984).

    Google Scholar 

  223. Yoshitomi Pharmaceutical Industries, Ltd., Jpn. Pat. 59112968;Chem Abstr.,101, 210996 (1984).

    Google Scholar 

  224. J. Verbeek, A. V. E. George, R. L. P. De Jong, and L. Brandsma,J. Chem. Soc., Chem. Commun., No. 4, 257 (1984).

    Google Scholar 

  225. J. Verbeek and L. Brandsma,J. Org. Chem.,49, 3857 (1984).

    Article  CAS  Google Scholar 

  226. P. Jacob, III, and A. T. Shulgin,Synth. Commun.,11, 957 (1981).

    CAS  Google Scholar 

  227. L. Engman and M. P. Cava,Organometallics,1, 470 (1982).

    Article  CAS  Google Scholar 

Download references

Authors

Additional information

Dedicated to Professor Henk van der Plas on his 70th birthday.

For No. 2, see [1].

M. V. Lomonosov Moscow State University, Moscow 119899

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 437–494, April, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yurovskaya, M.A., Mit'kin, O.D. Functionalization of pyridines. 3. Reactions forming a carbon-heteroatom bond with group IV, V, and VI elements. Chem Heterocycl Compd 35, 383–435 (1999). https://doi.org/10.1007/BF02319329

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02319329

Keywords

Navigation