Skip to main content
SpringerLink
Log in

Functionally-substituted Alkoxyethylenes in Reactions with Nucleophiles. Part I. Synthesis of Six-membered Heterocycles

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

REFERENCES

  1. Litvinov, V.P., Yakunin, Ya.Yu., and Dyachenko, V.D., Khim. Geterotsikl. Soed., 2001, no. 1, p. 41.

  2. Shainyan, B.A., Izv. SO Akad. Nauk SSSR, Ser. Khim., 1990. no. 4, p. 137.

  3. Rappoport, Z., Accounts Chem. Res., 1992, vol. 25, p. 474.

    Google Scholar 

  4. Stanovnic, B. and Svete, J., Synlett., 2000, p. 1077.

  5. Gorbunova, M.G., Gerus, I.I., and Kukhar, V.P., J. Fluor. Chem., 1993, vol. 65, p. 25.

    Google Scholar 

  6. Al-Jalal, N.A., J. Chem. Res. Synop., 1995, no. 2, p. 44.

  7. Zanatta, N., Fagundes, M.B., Ellensohn, R., Marques, M., Bonacorso, H.G., and Martins, M.A.P., J. Heterocycl. Chem., 1998, vol. 35, p. 451.

    Google Scholar 

  8. Tietze, L.F. and Schneider,C., Synlett., 1992, p. 755.

  9. Moriguchi, T., Endo, T., and Takata, T., J. Org. Chem., 1995, vol. 60, p. 3523.

    Google Scholar 

  10. Menicagli, R., Guagnano, V., and Malanga, C., Gazz. Chim. Ital., 1992, vol. 122, p. 487.

    Google Scholar 

  11. Bonacorso, H.G., Oliveira, M.R., Wentz, A.P., Wastowski, A.D., De, Oliveira, A.B., Hoerner, M., Zanatta, N., and Martins, M.A.P., Tetrahedron, 1999, vol. 55, p. 345.

    Google Scholar 

  12. Golec, J.M.C., Scrowston, R.M., and Dunleavy, M., J. Chem. Soc. Perkin Trans. I, 1992, p. 239.

  13. US Patent 5519139, 1996; Ref. Zh. Khim., 1998, 15 O 373P.

  14. Martin, W., De Biswanath, Zydowsky, T.M., Altenbach, R.J., Basha, F.Z., Boyd, S.A., Brune, M.E., Buckner, S.A., Crowell, A., Drizin, I., Hancock, A.A., Jae, H., Kester, J.A., Lee, J.Y., Mantei, R.A., Marsh, K.C., Novosad, E.I., Oheim, K.W., Rosenberg, S.H., Shiosaki, K., Sorensen, B.K., Spina, K., Sullivan, G.M., Tasker, A.S., Geldern, T.W., Warner, R.B., Opgenorth, T.J., Kerkman, D.J., and De Bernardis, J.F. J. Med. Chem., 1993, vol. 36, p. 2676.

    Google Scholar 

  15. Li, Y., Fang, F., Han, L., Wang, Q., and Shi, D., Qinghua daxue xuebao, J. Tsing-hua Univ., 1993, vol. 33, p. 79.

    Google Scholar 

  16. Ozeki,K., Ichikawa, T., Takehara, H., Tanimura, K., Sato, M., and Yaginuma, H., Chem. and Pharm. Bull., 1989, vol. 37, p. 1780.

    Google Scholar 

  17. Veale, C.A., Steelman, G.V., and Chow, M.M., J. Org. Chem., 1993, vol. 58, p. 4490.

    Google Scholar 

  18. Badawey, E.A.M. and Kappe, T., Arch. Pharm., 1997, vol. 330, p. 59.

    Google Scholar 

  19. Takagi, K., Bajnati, A., Hubert-Habart, M., and Terada, H., J. Heterocycl. Chem., 1990, vol. 27, p. 1847.

    Google Scholar 

  20. Bajnati, A., Hubert-Habart, M., Takagi, K., and Terada, H., Heterocycles, 1989, vol. 29, p. 1583.

    Google Scholar 

  21. Sansebastiano, L., Mosti, L., Menozzi, G., Schenone, P., Muratore, O., Petta, A., Debbia, E., Pesce, S.A., and Schito, G.C., Farmaco, 1993, vol. 48, p. 335.

    Google Scholar 

  22. Lemcke, T. and Messinger, P., Arch. Pharm., 1995, vol. 328, p. 269.

    Google Scholar 

  23. Masquelin, T., Sprenger, D., Baer, R., Gerber, F., and Mercadal, Y., Helv. Chim. Acta, 1998, vol. 81, p. 46.

    Google Scholar 

  24. Robev, S.K., Dokl. Bolg. Akad. Nauk, 1994, vol. 47, no. 9, p. 37.

    Google Scholar 

  25. Lorente, A., Vaquerizo, L., Martin, A., and Gomez-Sal, P., Heterocycles, 1995, vol. 41, p. 71.

    Google Scholar 

  26. McFadden, H.G. and Huppatz, J.L., Aust. J. Chem., 1992, vol. 45, p. 1045.

    Google Scholar 

  27. Yamazaki, C. and Miyamoto, Y., J. Heterocycl. Chem., 1996, vol. 33, p. 1285.

    Google Scholar 

  28. US Patent 5420128, 1995; Ref. Zh. Khim., 1997, 6 O 66P.

  29. El-Ashmawy, M.B., Shehata, I.A., El-Subbagh, H.I., and El-Emam, A.A., Gazz. Chim. Ital., 1991, vol. 121, p. 113.

    Google Scholar 

  30. Arun, D.S.V. and Chalapathi, R.C.V., Indian J. Chem. B, 1997, vol. 36, p. 810.

    Google Scholar 

  31. Bayomi, S.M., Al-Obaid, A.R., Jado, A.I., and Loutfy, E.A., Indian J. Chem. B., 1990, vol. 29, p. 47.

    Google Scholar 

  32. Bayomi, S.M., Al-Obaid, A.R.M., Jado, A.I., and Loutfy, E.A., Pharmazie, 1989, vol. 44, p. 814.

    Google Scholar 

  33. Murty, M.S.R., Ramalingam, T., and Sattur, P.B., J. Heterocycl. Chem., 1990, vol. 27, p. 949.

    Google Scholar 

  34. Ramalingam, T., Murty, M.S.R., Nageswar, Y.V.D., and Sattur, P.B., J. Heterocycl. Chem., 1990, vol. 27, p. 981.

    Google Scholar 

  35. Matosiuk, D., Tkaczynski, T., Jagiello-Wojtowich, E., Wielosz, M., Szurska, G., Chodkowska, A., Janusz, W., and Kleinroc, Z., Pol. J. Pharmacol. and Pharm., 1992, vol. 44, p. 307.

    Google Scholar 

  36. Nagai, S., Ueda, T., Takamura, M., Nagatsu, A., Murakami, N., and Sakakibara, J., J. Heterocycl. Chem., 1998, vol. 35, p. 293.

    Google Scholar 

  37. Nagai, S., Ueda, T., Nagatsu, A., Nakaoka, K., Murakami, N., Sakakibara, J., Fujita, M., and Hotta, Y., J. Heterocycl. Chem., 1998, vol. 35, p. 329.

    Google Scholar 

  38. Poland Patent 166371, 1995; Ref. Zh. Khim., 1996, 1 O 53P.

  39. Dave, C.G. and Shah, R.D., Heterocycles, 1999, vol. 51, p. 1819.

    Google Scholar 

  40. Pinto, S.E. and Fernandes, P.S., Indian J. Chem. V, 1994, vol. 33, p. 795.

    Google Scholar 

  41. Dennin, F., Blondeau, D., and Sliva, H., J. Heterocycl. Chem., 1990, vol. 27, p. 1639.

    Google Scholar 

  42. Dennin, F., Blondeau, D., and Sliva, H., J. Heterocycl. Chem., 1990, vol. 27, p. 1963.

    Google Scholar 

  43. Dennin, F., Blondeau, D., and Sliva, H., J. Heterocycl. Chem., 1991, vol. 28, p. 1287.

    Google Scholar 

  44. Ram, V.J., Kushwaha, D.S., Mishra, L., Indian J. Chem. V, 1989, vol. 28, p. 242.

    Google Scholar 

  45. Badawey, E. and Kappe, T., J. Heterocycl. Chem., 1995, vol. 32, p. 1003.

    Google Scholar 

  46. Romano, C., Cuesta, E., and Avendaro, C., Heterocycles, 1990, vol. 31, p. 267.

    Google Scholar 

  47. Quiroga, J., Hormaza, A., Insuasty, B., Saitz, C., Jullian, C., and Canete, A., J. Heterocycl. Chem., 1998, vol. 35, p. 61.

    Google Scholar 

  48. Srivastava, R.P., Singh, S.K., Abuzar, S., Sharma, S., Gupta, S., Katiyar, J.C., and Chatterjee, R.K., Indian J. Chem. V., 1993, vol. 32, p. 1035.

    Google Scholar 

  49. Srivastava, R.P., Kumar, V.V., Bhatia, S., and Sharma, S., Indian J. Chem. V., 1995, vol. 34, p. 209.

    Google Scholar 

  50. Sano, A., Ishihara, M., Yoshihara, J., Sumino, M., and Nawa, H., Chem. and Pharm. Bull., 1995, vol. 43, p. 683.

    Google Scholar 

  51. Japan Patent 2289569, 1990; Ref. Zh. Khim., 1993, 22 O 41P.

  52. Sherif, S.M. and Hussein, A.M., Monatsh. Chem., 1997, 128, p. 687.

    Google Scholar 

  53. Elgemeie, G.H., Elghandour, A.H., and Elshimy, H.M., J. Prakt. Chem., 1989, vol. 331, p. 466.

    Google Scholar 

  54. El-Hamid, A.A., Essawy, A., and Amer, A.M., 4th Ibn Sina Int. Symp. Pure and Appl. Heterocycl. Chem., Cairo, 1992, p. 17.

  55. Deady, L.W., Mackay, M.F., and Werden, D.M., J. Heterocycl. Chem., 1989, vol. 26, p. 161.

    Google Scholar 

  56. Sano, A. and Ishihara, M., Heterocycles, 1998, vol. 48, p. 775.

    Google Scholar 

  57. Mikhalev, A.I., Suslina, M.L., Kon'shina, T.M., Zaks, A.S., and Kon,shin, M.E., Khim.-Farm. Zh., 1995, vol. 29, p. 39.

    Google Scholar 

  58. Abbas, T.H.H., Younes, M.I., and Metwally, S.A., Collect. Czechosl. Chem. Commun., 1993, vol. 58, p. 3017.

    Google Scholar 

  59. Bruni, F., Selleri, S., Costanzo, A., Guerrini, G., Casilli, M.L., and Giusti, L., J. Heterocycl. Chem., 1995, vol. 32, p. 291.

    Google Scholar 

  60. Al-Shaar, A.H.M., Chambers, R.K., Gilmour, D.W., Lythgoe, D.J., McClenaghan, I., and Ramsden,C.A., J. Chem. Soc. Perkin Trans. 1, 1992, no. 21, p. 2789.

    Google Scholar 

  61. Chimichi, S., Cosimelli, B., Bruni, F., and Costanzo, A., J. Chem. Soc. Perkin Trans. 2, 1995, no. 2, p. 209.

  62. Agathocieous, D.C., Moharram, H.H., and Shaw,G., J. Chem. Res. (S)., 1990, no. 11, p. 374.

  63. Hirota, K., Sajiki, H., Kitade, Y., and Maki, Y., Chem. and Pharm. Bull., 1989, vol. 37, p. 2008.

    Google Scholar 

  64. Michne, W.F., Schroeder, J.D., Guiles, J.W., Treasurywala, A.M., Weigelt, C.A., Stansberry, M.F., McAvoy, E., Shan, C.R., Baine, Y., Sawutz, D.G., Miller, F.B., Stankunas, B.M., Reid, J., Bump, E., and Schlegel, D., J. Med. Chem., 1995, vol. 38, p. 2557.

    Google Scholar 

  65. Sabatini, S., Cecchetti, V., Tabarrini, O., and Fravolini, A., J. Heterocycl. Chem., 1999, vol. 36, p. 953.

    Google Scholar 

  66. Erian, A.W., Monatsh. Chem., 1998, vol. 129, p. 1049.

    Google Scholar 

  67. El-Abadelah, M.M., Sabri, S.S., and Al-Ashqar, H.A., Heterocycles, 1997, vol. 45, p. 255.

    Google Scholar 

  68. Song, H.J., Kim, M.Y., Kang, S.B., Chung, B.Y., and Kim, Y., Heterocycles, 1998, vol. 48, p. 10Z.

    Google Scholar 

  69. US Patent 4824474, 1989; Ref. Zh. Khim., 1990, 7 O 452P.

  70. US Patent 4902685, 1990; Ref. Zh. Khim., 1991, 2 O 74P.

  71. Cocco, M.T., Congiu, C., Maccioni, A., and Plumitallo, A., J. Heterocycl. Chem., 1989, vol. 26, p. 1859.

    Google Scholar 

  72. Cocco, M.T., Congiu, C., and Maccioni, A., J. Heterocycl. Chem., 1990, vol. 27, p. 1143.

    Google Scholar 

  73. Cocco, M.T., Congiu, C., Maccioni, A., and Onnis, V., J. Heterocycl. Chem., 1992, vol. 29, p. 1631.

    Google Scholar 

  74. Cocco, M.T., Congiu, C., Onnis, V., and Maccioni, A., J. Heterocycl. Chem., 1991, vol. 28, p. 797.

    Google Scholar 

  75. Pyrko, A.N., Khim. Geterotsikl. Soed., 1999, no. 6, p. 774.

  76. Fuentes, L., Marquez, C., Contreras, C., Lorenzo, J., Fonseca, I., Sanz-Aparicio, J., and Balcazar, J.L., J. Heterocycl. Chem., 1995, vol. 32, p. 29.

    Google Scholar 

  77. Trapani, G., Latrofa, A., Franco, M., Liso, G., and Genchi, G., Farmaco, 1990, vol. 45, p. 589.

    Google Scholar 

  78. Ramesh, B.V.N.S., Narahari, B.A., Anand, V., and Hanumanthu, P., Synth. Commun., 1998, vol. 28, p. 4439.

    Google Scholar 

  79. Benovsky, P. and Stille, J.R., Tetrahedron Lett., 1997, vol. 38, p. 8475.

    Google Scholar 

  80. Nawwar, G.A.M., Zaki, M.M.E.A., and Chabaka, L.M., Phosph. Sulfur and Silicon and Relat. Elem., 1993, vol. 79, p. 195.

    Google Scholar 

  81. Dyachenko, V.D. and Tkachev, R.P., Zh. Org. Khim., 2002, vol. 38, p. 768.

    Google Scholar 

  82. Tkachev, R.P., Yakunin, Ya.Yu., and Dyachenko, V.D., Abstracts of Papers, Organicheskaya khimiya v XX veke (Organic Chemistry on 20th Century), Moskva, 2000, p. 23.

  83. Dyachenko, V.D. and Tkachev, R.P., Abstracts of Papers, Strategiya i taktika organicheskogo sinteza (Strategy and Tactics of Organic Synthesis), Yaroslavl, 2001, p. 43.

  84. Tkachov, R.P. and Dyachenko, V.D., Abstracts of Papers, XIX Ukrains'ka, konferentsiya z organichnoi khimii (19th Ukrainian Conf. on Organic Chemistry), L'viv, 2001, p. 533.

  85. Yakunin, Ya.Yu., Dyachenko, V.D., and Litvinov, V.P., Izv. Russian, Akad. Nauk, Ser. Khim., 1999, no. 1, p. 196.

  86. Yakunin, Ya.Yu., Dyachenko, V.D., and Litvinov, V.P., Khim. Geterotsikl. Soed., 2000, no. 12, p. 1667.

  87. Yakunin, Ya.Yu., Dyachenko, V.D., Rusanov, E.B., and Litvinov, V.P., Khim. Geterotsikl. Soed., 2001, no. 2, p. 224.

  88. Yakunin, Ya.Yu., Dyachenko, V.D., and Litvinov, V.P., Abstracts of Papers, XX Vserossiiskaya konferentsiya po khimii i tekhnologiii organicheskikh soedinenii sery (20th All-Russian Conf. on Chemistry and Technology Organic Chemistry of Sulfur), Kazan, 1999, p. 174.

  89. Yakunin, Ya.Yu. and Dyachenko, V.D., Khimiya azotvmisnikh geterotsiklov (Chemistry of Nitrogen Heterocycles), Kharkiv, 2000, p. 20.

  90. Hagen, V., Rumler, A., Reck, G., Hagen, A., Labes, D., and Heer, S., Pharmazie, 1989, vol. 44, p. 809.

    Google Scholar 

  91. Elneairy, M.A.A., Abdel-Rahman, T.M., and Hammad, A.M., J. Chem. Res. Synop., 1998, no. 11, p. 684.

  92. Inouye, M., Kim, K., and Kitao, T., J. Amer. Chem. Soc., 1992, vol. 114, p. 778.

    Google Scholar 

  93. Elgemeie, G.E.H. and Mahfouz, R.M.M., Phosph. Sulfur and Silicon, and Relat. Elem., 1989, vol. 46, p. 95.

    Google Scholar 

  94. Monnet, M.O., Fauret, T., Levacher, V., Dupas, G., Bourguignon, J., and Queguiner, G., J. Heterocycl. Chem., 1989, vol. 26, p. 1029.

    Google Scholar 

  95. Russell, R.K. and Lever, O.W., J. Synth. Commun., 1993, vol. 23, p. 2931

    Google Scholar 

  96. Abe, N., Bull. Chem. Soc. Jap., 1991, vol. 64, p. 2393.

    Google Scholar 

  97. Abdalla, G.M. and Sowell, Sr. J. Walter, J. Heterocycl. Chem., 1990, vol. 27, p. 1201.

    Google Scholar 

  98. Bare, T.M., McLaren, C.D., Campbell, J.B., Firor, J.W., Resch, J.F., Walters, C.P., Salama, A.I., Meiners, B.A., and Patel, J.B., J. Med. Chem., 1989, vol. 32, p. 2561.

    Google Scholar 

  99. Melani, F., Cecchi, L., Colotta, V., Filacchioni, G., Martini, C., Giannaccini, G., and Lucacchini, A., Farmaco, 1989, vol. 44, p. 585.

  100. Richardson, T.O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, vol. 32, p. 359.

    Google Scholar 

  101. Bhupathy, M., Conlon, D.A., Wells, K.M., Nelson, J.R., Reider, P.J., Rossen, K., Sager, J.W., Volante, R.P., Dorsey, B.D., Hoffman, J.M., Joseph, S.A., and McDaniel, S.L., J. Heterocycl. Chem., 1995, vol. 32, p. 1283.

    Google Scholar 

  102. Malicorne, G., Bompart, J., Giral, L., and Despaux, E., Eur. J. Med. Chem., 1991, vol. 26, p. 3.

    Google Scholar 

  103. Bacon, E.R. and Daum, S.J., J. Heterocycl. Chem., 1991, vol. 28, p. 1953.

    Google Scholar 

  104. French Patent 2632639, 1989; Ref. Zh. Khim., 1990, 15 O 41P.

  105. Barlin, G.B. and Jiravinyu, C., Austral. J. Chem., 1990, vol. 43, p. 1175.

    Google Scholar 

  106. Radl, S. and Hradil, P., Collect. Czechosl. Chem. Commun., 1991, vol. 56, p. 2240.

    Google Scholar 

  107. Singh, B., Laskowski, S.C., and Lesher, G.Y., Synlett., 1990, p. 549.

  108. Al-Mousawi, S.M., Kaul, K., Mohammad, M.A., and Elnagdi, M.H., J. Chem. Res. Synop., 1997, no. 9, p. 318.

  109. Ahmed, G.A., J. Indian Chem. Soc., 1997, vol. 74, p. 624.

    Google Scholar 

  110. Hussein, A.M. and El-Emary, T.I., J. Chem. Res. Synop., 1998, no. 1, p. 20.

  111. Trkovnik, M. and Ivezic, Z., J. Heterocycl. Chem., 2000, vol. 37, p. 137.

    Google Scholar 

  112. Garcia, J.A., Sanchez, A., and Nogueras, M., J. Heterocycl. Chem., 1989, vol. 26, p. 1089.

    Google Scholar 

  113. Matsuda, Y., Gotou, H., Katou, K., Matsumoto, H., Yamashita, M., Takahashi, K., and Ide, S., Heterocycles, 1990, vol. 31, p. 977.

    Google Scholar 

  114. Matsuda, Y., Gotou, H., Katou, K., Matsumoto, H., Yamashita, M., Takahashi, K., Ide, S., Furuno, K., and Torisu, K., J. Heterocycles, 1991, vol. 32, p. 2217.

    Google Scholar 

  115. Matsuda, Y., Chiyomaru, Y., Motokawa, C., and Nishiyori, T., Heterocycles, 1995, vol. 41, p. 329.

    Google Scholar 

  116. Matsuda, Y., Katou, K., Nishiyori, T., Uemura, T., and Urakami, M., Heterocycles, 1997, vol. 45, p. 2197.

    Google Scholar 

  117. Verboom, W., Verboom, C., Eissink, I.M., Lammerink, B.H.M., and Reinhoudt, D.N., Rec. Trav. Chim. Pays-Bas., 1990, vol. 109, p. 481.

    Google Scholar 

  118. Maclaren, J.A., Austral J. Chem., 1989, vol. 42, p. 813.

    Google Scholar 

  119. Duindam, A., Lishinsky, V.L., and Sikkema, D.J., Synth. Commun., 1993, vol. 23, p. 2605.

    Google Scholar 

  120. Pilosyan, S.G., Dabaeva, V.V., Enokyan, B.Dzh., Abgaryan, E.A., and Noravyan, A.S., Arm. Khim. Zh., 1988, vol. 41, p. 687.

    Google Scholar 

  121. Litvinov, V.P., Roman, S.V., and Dyachenko, V.D., Uspekhi Khimii (in print).

  122. French Patent 2767822, 1999; Ref. Zh. Khim., 00.18-19O.61P.

  123. Cooper, C.S., Klock, P.L., Chu, D.T.W., and Fernandes, P.B., J. Med. Chem., 1990, vol. 33, p. 1246.

    Google Scholar 

  124. Venugopalan, V., De Souza, E.P., Sathe, K.M., Chatterjee, D.K., and Iycn, N., Indian J. Chem. V, 1995, vol. 34, p. 778.

    Google Scholar 

  125. Swiss Patent 685560, 1995; Ref. Zh. Khim., 1996, 14 O 48P.

  126. Japan Patent 2157282, 1990; Ref. Zh. Khim., 1993, 3 O 177P.

  127. Awasthi, V. and Chauhan, S.M.S., Indian J. Chem. V, 1991, vol. 30, p. 352.

    Google Scholar 

  128. US Patent 5973153, 1999; Ref. Zh. Khim., 00.17-19N.97P.

  129. Wang, T.S.T., Fawwaz, R.A., and Van, H.R.L., J. Labell. Compounds and Radiopharm., 1995, vol. 36, p. 313.

    Google Scholar 

  130. Blurton, P., Brickwood, A., and Dhanak, D., Heterocycles, 1997, vol. 45, 2395.

    Google Scholar 

  131. Gruzdev, V.A. and Dokichev, V.G., Abstracts of Papers, 9 Vseross. konf. po khim. reaktivam REAKTIV-96 “Khim. reaktivy, reagenty i protsessy malotonnazh. Khimii” (9th All-Russian Conf. on Chemical Reactives “REACTIV-96: Chemical Reactives, Reagents, and Small-Scale Chemistry Processes)”, Ufa, 1996, p. 126.

  132. Lowe,W. and Dietz,M., Sci. Pharm., 1996, vol. 64, p. 555.

    Google Scholar 

  133. Glushkov, R.G., Vozyakova, T.I., Adamskaya, E.V., Gus'kova, T.A., Pushkina, T.V., Radkevich, T.P., and Solov'eva, N.P., Khim.-Farm. Zh., 1998, vol. 32, p. 10.

    Google Scholar 

  134. Nagaiah, K., Krupadanam, G.L. David, and Srimannarayana, G., Indian. J. Chem. V., 1998, vol. 37, p. 728.

    Google Scholar 

  135. Kidwai, M., Misra, P., Kumar, R., Saxena, R.K., Gupta, R., and Bradoo, S., Monatsh. Chem., 1998, vol. 129, p. 961.

    Google Scholar 

  136. Wentland, M.P., Lesher, G.Y., Reuman, M., Gruett, M.D., Singh, B., Aldous, S.C., Dorff, P.H., Rake, J.V., and Coughlin, S.A., J. Med. Chem., 1993, vol. 36, p. 2801.

    Google Scholar 

  137. Denny, W.A., Atwell, C.J., Roberts, P.B., Anderson, R.F., Boyd, M., Lock, C.J.L., and Wilson, W.R., J. Med. Chem., 1992, vol. 35, p. 4832.

    Google Scholar 

  138. Radl, S., Collect. Czechosl. Chem. Commun., 1994, vol. 59, p. 2119.

    Google Scholar 

  139. Russian Patent 2052454, 1996; Ref. Zh. Khim., 1996, 16 O 55P.

  140. US Patent 5103040, 1992; Ref. Zh. Khim., 1993, 11 O 28P.

  141. Chattopadhyay, J. and Basu, S.K., Indian. J. Chem. V., 1990, vol. 29, p. 98.

    Google Scholar 

  142. Nuvde, A., Sanna, P., Paglietti, G., Juliano, C., Zanetti, S., and Cappuccinelli, P., Farmaco, 1989, vol. 44, p. 619.

    Google Scholar 

  143. Sanna, P. and Paglietti, G., Farmaco, 1989, vol. 44, p. 609.

    Google Scholar 

  144. Brana, M.F., Castellano, J.M., and Yunta, M.J.R., J. Heterocycl. Chem., 1990, vol. 27, p. 1177.

    Google Scholar 

  145. Zhang, M.Q., Haemers, A., Vanden, B.D., Pattyn, S.R., Bollaert, W., and Levshin, I., J. Heterocycl. Chem., 1991, vol. 28, p. 673.

    Google Scholar 

  146. Zhang, M.Q., Haemers, A., Vanden, B.D., Pattyn, S.R., Bollaert, W., and Levshin, I., J. Heterocycl. Chem., 1991, vol. 28, p. 685.

    Google Scholar 

  147. Jolivet, C., Rivalle, C., and Bisagni, E., Heterocycles, 1996, vol. 43, p. 995.

    Google Scholar 

  148. Burke, T.R., Lim, B., Marquez, V.E., Li, Z., Bolen, J.V., Stefanova, I., and Horak, I.D., J. Med. Chem., 1993, vol. 36, p. 425.

    Google Scholar 

  149. Richardson, T.O., Shanbhag, V.P., Adair, K., and Smith, S., J. Heterocycl. Chem., 1998, vol. 35, p. 1301.

    Google Scholar 

  150. US Patent 4940710, 1990; Ref. Zh. Khim., 1991, 22 O 58P.

  151. US Patent 4914110, 1990; Ref. Zh. Khim., 1991, 11 O 64P.

  152. Austrian Patent 389119, 1989; Ref. Zh. Khim., 1990, 22 O 107P.

  153. US Patent 4822801, 1989; Ref. Zh. Khim, 1990, 16 O 129P.

  154. US Patent 4868305, 1989; Ref. Zh. Khim., 1990, 16 O 128P.

  155. Japan Patent 1-265088, 1989; Ref. Zh. Khim, 1991, 4 O 112P

  156. Japan Patent 2288864, 1990; Ref. Zh. Khim., 1992, 18 O 56P.

  157. Hashimoto, K., Okaichi, Y., Nomi, D., Miyamoto, H., Bando, M., Kido, M., Fujimura, T., Furuta, T., and Minamikawa, J., Chem. and Pharm. Bull., 1996, vol. 44, p. 642.

    Google Scholar 

  158. Tsuji, K., Tsubouchi, H., and Ishikawa, H., Chem. and Pharm. Bull., 1995, vol. 43, p. 1678.

    Google Scholar 

  159. Ishikawa, H., Tabusa, F., Miyamoto, H., Kano, M., Ueda, H., Tamaoka, H., and Nakagawa, K., Chem. and Pharm. Bull., 1989, vol. 37, p. 2103.

    Google Scholar 

  160. Ishikawa, H., Uno, T., Miyamoto, H., Ueda, H., Tamaoka, H., Tominaga, M., and Nakagawa, K., Chem. and Pharm. Bull., 1990, vol. 38, p. 2459.

    Google Scholar 

  161. El-Subbagh, H.I., Abadi, A.H., Al-Khawad, I.E., and Al-Rashood, K.A., Arch. Pharm., 1999, vol. 332, p. 19.

    Google Scholar 

  162. Sabnis, R.W. and Rangnekar, D.W., J. Heterocycl. Chem., 1991, vol. 28, p. 1105.

    Google Scholar 

  163. Sabnis, R.W. and Rangnekar, D.W., J. Heterocycl. Chem., 1992, vol. 29, p. 65.

    Google Scholar 

  164. Japan Patent 1-250380, 1989; Ref. Zh. Khim., 1991, 18 O 81P.

  165. US Patent 4946844, 1990; Ref. Zh. Khim., 1991, 21 O 57P.

  166. US Patent 4985557, 1991; Ref. Zh. Khim., 1992, 15 O 105P.

  167. Japan Patent 1228974, 1989; Ref. Zh. Khim., 1991, 13 O 110P.

  168. Danish Patent 159778, 1990; Ref. Zh. Khim., 1991, 20 O 48P.

  169. Japan Patent 2138281, 1990; Ref. Zh. Khim., 1992, 2 O 143P.

  170. Leach, C.A., Brown, T.H., Ife, R.J., Keeling, D.J., Parsons, M.E., Theobald, C.J., and Wiggall, K.J., J. Med. Chem., 1995, vol. 38, p. 2748.

    Google Scholar 

  171. Milata, V., Ilavsky, D., Chudik, M., Zalibera, L., Lesko, J., Seman, M., and Belicova, A., Monatsh. Chem., 1995, vol. 126, p. 1349.

    Google Scholar 

  172. Salon, J., Milata, V., Pronayova, N., and Lesko, J., Monatsh. Chem., 2000, vol. 131, p. 293.

    Google Scholar 

  173. Milata, V., Ilavsky, D., Coljer, I., Lesko, J., Chahinian, M., and Henry-Basch, E., Collect. Czechosl. Chem. Commun., 1990, vol. 55, p. 1038.

    Google Scholar 

  174. Bobosik, V., Milata, V., Ilavsky, D., and Coljer, I., Collect. Czechosl. Chem. Commun., 1992, vol. 57, p. 397.

    Google Scholar 

  175. Zubkov, V.O., XIX Ukrains'ka konferentsiya z organichnoi khimii (19th Ukrainian Conf. on Organic Chemistry), L'viv, 2001, p. 297.

  176. US Patent 6002008, 1999; Ref. Zh. Khim.,00.24-19O.221P.

  177. Marcos, A., Pedregal, C., and Avendano, C., Tetrahedron., 1995, vol. 51, p. 1763.

    Google Scholar 

  178. Grandjean, D., Dhimane, H., Pommelet, J., and Chuche, J., Bull. Soc. Chim. Fr., 1989, no. 5, p. 657.

  179. US Patent 4822801, 1989; Ref. Zh. Khim., 1990, 15 O 70P.

  180. Forbes, I.T., Johnson, C.N., Jones, G.E., Loudon, J., Nicholass, J.M., Thompson, M., and Upton, N., J. Med. Chem., 1990, vol. 33, p. 2640.

    Google Scholar 

  181. Adrio, J., Carretero, J.S., Garcia, R.J.L., Pallares, A., and Vicioso, M., Heterocycles, 1999, vol. 51, p. 1563.

    Google Scholar 

  182. US Patent 4864023, 1989; Ref. Zh. Khim., 1990, 21 O 80P.

  183. US Patent 5563138, 1996; Ref. Zh. Khim., 1998, 24 O 129P.

  184. US Patent 4874764, 1989; Ref. Zh. Khim., 1990, 23 O 48P.

  185. Hradil, P., Acta Univ. Palack. Olomuc. Fac. Rerum. Natur. Chem., 1995, no. 34, p. 29.

  186. Heleyova, K. and Ilavsky, D., Monatsh. Chem., 1995, vol. 126, p. 1359.

    Google Scholar 

  187. Heleyova, K. and Ilavsky, D., Collect. Czechosl. Chem. Commun., 1997, vol. 62, p. 99.

    Google Scholar 

  188. French Patent 2632305, 1989; Ref. Zh. Khim., 1990, 15 O 40P.

  189. Moinet-Hedin, V., Tabka, T., Gauduchon, P., Le Talaer, J.Y., Letois, B., Lancelot, J.C., Rault, S., and Robba, M., Eur. J. Med. Chem., 1993, vol. 28, p. 721.

    Google Scholar 

  190. Oh, Y., Lee, C., Chung, Y., Yoon, S., and Cho, S., J. Heterocycl. Chem., 1998, vol. 35, p. 541.

  191. Oh, Y. and Cho, S., J. Heterocycl. Chem., 1998, vol. 35, p. 17.

    Google Scholar 

  192. US Patent 5175356, 1992; Ref. Zh. Khim., 1994, 9 O 68P.

  193. Sanchez, J.P., Bridges, A.J., Bucsh, R., Domagala, J.M., Gogliotti, R.D., Hagen, S.E., Heifetz, C.L., Joannides, E.T., Sesnie, J.C., Shapiro, M.A., and Szotek, D.L., J. Med. Chem., 1992, vol. 35, p. 361.

    Google Scholar 

  194. Hagen, S.E., Domagala, J.M., Heifetz, C.L., and Johnson, J., J. Med. Chem., 1991, vol. 34, p. 1155.

    Google Scholar 

  195. Domagala, J.M., Bridges, A.J., Culbertson, T.P., Cambino, L., Hagen, S.E., Karrick, G., Porter, K., Sanchez, J.P., Segnie, J.A., Spense, F.G., Szotek, D., and Wemple, J., J. Med. Chem., 1991, vol. 34, p. 1142.

    Google Scholar 

  196. US Patent 5081254, 1992; Ref. Zh. Khim., 1993, 14 O 73P.

  197. US Patent 5116834, 1992; Ref. Zh. Khim., 1993, 15 O 85P.

  198. Renau, T.E., Sanchez, J.P., and Domagala, J.M., J. Heterocycl. Chem., 1996, vol. 33, p. 1407.

    Google Scholar 

  199. Bouzard, D., Di, Cesare, P., Essiz, M., Jacquet, J.P., Ledoussal, B., Remuzon, P., Kessler, R.E., and Fung-Tome, J., J. Med. Chem., 1992, vol. 35, p. 518.

    Google Scholar 

  200. Bouzard, D., Di Cesare, P., Essiz, M., Jacquet, J.P., Remuzon, P., Weber, A., Oki, T., and Masuyoshi, M., J. Med. Chem., 1989, vol. 32, p. 537.

    Google Scholar 

  201. Guillou, C.C., Remuzon, P., Bouzard, D., Quirion, J., Giorgi-Renault, S., and Husson, H., Tetrahedron, 1998, vol. 54, p. 83.

    Google Scholar 

  202. Bouzard, D., Cesare, P.Di., Essiz, M., Jacquet, J.P., Kiechel, J.R., Remuzon, P., Weber, A., Oki, T., Masuyoshi, M., Kessler, R.E., Fung-Tome, J., and Desiderio, J., J. Med. Chem., 1990, vol. 33, p. 1344.

    Google Scholar 

  203. Ledoussal, B., Bouzard, D., and Coroneos, E., J. Med. Chem., 1992, vol. 35, p. 198.

    Google Scholar 

  204. Xiao, W., Krishnan, R., Lin, Y.-I., Santos, E.F., Delos, Kuck, N.A., Babine, R.E., and Lang, S.A., Jr., J. Pharm. Sci., 1989, vol. 78, p. 585.

    Google Scholar 

  205. Moran, D.B., Ziegler, C.B., Jr., Dunne, T.S., Kuck, N.A., and Lin, Y., J. Med. Chem., 1989, vol. 32, p. 1313.

    Google Scholar 

  206. Glushkov, R.G., Marchenko, N.B., Levshin, I.B., and Dronova, L.N., Khim.-Farm. Zh., 1997, vol. 31, p. 48.

    Google Scholar 

  207. Glushkov, R.G., Marchenko, N.B., and Levshin, I.B., Khim.-Farm. Zh., 1997, vol. 31, p. 23.

    Google Scholar 

  208. Obanin, G.A., Fokin, A.S., Burgart, Ya.V., Ryzhkov, O.V., Skryabina, Z.E., Saloutin, V.I., and Chupakhin, O.N., Izv. Akad. Nauk, Ser. Khim., 2000, no. 7, p. 1234.

  209. Augeri, D.J., Fray, A.H., and Kleinman, E.F., J. Heterocycl. Chem., 1990, vol. 27, p. 1509.

    Google Scholar 

  210. Chu, D.T.W., Nordeen, C.W., Hardy, D.J., Swanson, R.N., Giardina, W.J., Pernet, A.G., and Plattner, J.J., J. Med. Chem., 1991, vol. 34, p. 168.

  211. Int. RST Patent 8905643, 1989; Ref. Zh. Khim., 1990, 5 O 199P.

  212. US Patent 5037834, 1991; Ref. Zh. Khim., 1993, 6 O 94P.

  213. Ekhato, I.V. and Huang, C.C. J. Labell., Compounds and Radiopharm., 1993, vol. 33, p. 869.

    Google Scholar 

  214. J'rgens, J., Schedletzky, H., Heisig, P., Seydel, J.K., Wiedemann, B., and Holzgrabe, U., Arch. Pharm., 1996, vol. 329, p. 179.

    Google Scholar 

  215. German Patent 4303657, 1994; Ref. Zh. Khim., 1995, 21 O 55P.

  216. Laborde, E., Kiely, J.S., Culbertson, T.P., and Lesheski, L.E., J. Med. Chem., 1993, vol. 36, p. 1964.

    Google Scholar 

  217. Chen,Y., Dai, L., Yang, B., and Hong, C., J. Chem. Eng. Chin. Univ., 1999, vol. 13, p. 368.

    Google Scholar 

  218. Okada, T., Tsuji, T., Tsushima, T., Yoshida, T., and Matsuura, S., J. Heterocycl. Chem., 1991, vol. 28, p. 1061.

    Google Scholar 

  219. US Patent 5043450, 1991; Ref. Zh. Khim., 1993, 1 O 51P.

  220. US Patent 5073556, 1991; Ref. Zh. Khim., 1993, 7 O 141P.

  221. Japan Patent 37261, 1991; Ref. Zh. Khim., 1993, 7 O 142P.

  222. US Patent 5164392, 1992; Ref. Zh. Khim., 1994, 5 O 114P.

  223. McGuirk, P.R., Jefson, M.R., Mann, D.D., Elliot, N.C., Chang, P., Ciesek, E.P., Cornell, C.P., Grootz, T.D., Haskell, S.L., Hindahl, M.S., La Fleur, L.J., Rosenfeld, M.J., Shryock, T.R., Silvia, A.M., and Weber, F.H., J. Med. Chem., 1992, vol. 35, p. 612.

    Google Scholar 

  224. US Patent 5998436, 1999; Ref. Zh. Khim., 00.23-19O.101P.

  225. US Patent 4965273, 1990; Ref. Zh. Khim., 1992, 7 O 66P.

  226. German Patent 3906365, 1990; Ref. Zh. Khim., 1992, 3 O 153P.

  227. German Patent 4120646, 1992; Ref. Zh. Khim., 1994, 6 O 96P.

  228. Japan Patent 228157, 1990; Ref. Zh. Khim., 1991, 17 O 137P.

  229. Japan Patent 2131453, 1990; Ref. Zh. Khim., 1991, 15 O 64P.

  230. US Patent 4920120, 1990; Ref. Zh. Khim., 1991, 14 O 119P.

  231. Japan Patent 64-83067, 1989; Ref. Zh. Khim., 1990, 13 O 40P.

  232. Japan Patent 63-198664, 1988; Ref. Zh. Khim., 1990, 9 O 167P.

  233. US Patent 4929613, 1990; Ref. Zh. Khim., 1991, 13 O 195P.

  234. US Patent 4855292, 1989; Ref. Zh. Khim., 1991, 21 O 160P.

  235. Japan Patent 219377, 1990; Ref. Zh. Khim., 1991, 18 O 175P.

  236. Int. RST Patent 91/04972, 1991; Ref. Zh. Khim., 1992, 13 O 144P.

  237. Japan Patent 64-22854, 1989; Ref. Zh. Khim., 1990, 5 O 198P.

  238. US Patent 4933335, 1990; Ref. Zh. Khim., 1991, 23 O 113P.

  239. Japan Patent 2124873, 1990; Ref. Zh. Khim., 1992, 11 O 132P.

  240. Miao, H., Cecchetti, V., Tabarrini, O., and Fravolini, A., J. Heterocycl. Chem., 2000, vol. 37, p. 297.

    Google Scholar 

  241. Japan Patent 649992, 1989; Ref. Zh. Khim., 1990, 1 O 328P.

  242. Lipunova, G.N., Nosova, E.V., Charushin, V.N., Sidorova, L.P., and Chasovskikh, O.M., Mendeleev Commun., 1998, no. 4, p. 131.

  243. Norcini, G., Allievi, L., Bertolini, G., Casagrande, C., Miragoli, G., Santangelo, F., and Semeraro, C., Eur. J. Med. Chem., 1993, vol. 28, p. 505.

    Google Scholar 

  244. Moglioni, A.G., Martinez, A.R., Sosnik, A.D., and Iglesias, G.Y.M., J. Chem. Res. Synop., 1996, no. 11, p. 500.

  245. Boger, D.L. and Mullican, M.D., Org. Synth.: Annu. Publ. Satisfact. Meth. Prep. Org. Chem., New York, 1987, vol. 65, p. 98.

  246. Merour, J.Y. and Cossais, F., J. Heterocycl. Chem., 1991, vol. 28, p. 1875.

    Google Scholar 

  247. Kepe, V., Kocevar, M., and Polanc, S., Heterocycles, 1995, vol. 41, p. 1299.

    Google Scholar 

  248. Kepe, V., Kocevar, M., Polanc, S., Vercek, B., and Tisler, M., Tetrahedron, 1990, vol. 46, p. 2081.

    Google Scholar 

  249. Kepe, V., Kocevar, M., Petric, A., Polanc, S., and Vercek, B., Heterocycles, 1992, vol. 33, p. 843.

    Google Scholar 

  250. Ahluwalia, V.K., Sharma, R., and Sharma, M.K., Indian J. Chem. B., 1992, vol. 31, p. 688.

    Google Scholar 

  251. Ahluwalia, V.K., Garg, V.K., Dahiya, A., and Alauddin, M.D., Indian J. Chem. V., 1995, vol. 34, p. 51.

    Google Scholar 

  252. Ahluwalia, V.K., Dudeja, S., Sahay, R., and Kumar, R., Indian J. Chem. B., 1996, vol. 35, p. 1319.

    Google Scholar 

  253. Kakehi, A., Ito, S., and Matsubara, K., Bull. Chem. Soc. Jap., 1995, vol. 68, p. 2409.

    Google Scholar 

  254. Kvita, V., Helv. Chim. Acta, 1990, vol. 73, p. 411.

    Google Scholar 

  255. Saloutin, V.I., Skryabina, Z.E., Bazyl', I.T., and Chupakhin, O.N., Izv. Akad. Nauk. Ser. Khim., 1993, no. 2, p. 362.

  256. Gorbulenko, N.V., Khilya, V.P., and Kirpa, S.A., Dokl. Akad. Nauk USSR, B., 1990, no. 12, p. 22.

  257. Hegde, V., Hung, C., Madhukar, P., Cunningham, R., Htspfner, T., and Thummel, R.P., J. Amer. Chem. Soc., 1993, vol. 115, p. 872.

    Google Scholar 

  258. Hojo, M., Masuda, R., and Okada, E., Synthesis (BRD), 1990, no. 4, p. 347.

  259. Abe, N., Odagiri, K., and Kakehi, A., J. Chem. Soc. Perkin. Trans. I, 1997, no. 15, p. 2189.

  260. Abe, N., Odagiri, K., Fujii, H., and Kakehi, A., Heterocycles, 2000, vol. 53, p. 323.

    Google Scholar 

  261. Abe, N., Odagiri, K., Otani, M., Fujinaga, E., Fujii, H., and Kakehi, A., J. Chem. Soc. Perkin Trans. I, 1999, no. 10, p. 1339.

  262. Matsuda, Y., Chiyomaru, Y., Furuno, K., and Nishiyori, T., Heterocycles, 1995, vol. 41, p. 2777.

  263. Brimble, M.A. and Johnston, A.D., Tetrahedron, 1994, vol. 50, p. 4887.

    Google Scholar 

  264. Wessig, P. and Schwarz, J., Monatsh. Chem., 1995, vol. 126, p. 99.

    Google Scholar 

  265. El-Sayed, A.M., Abdel-Ghany, H., and El-Saghier, A.M.M., Synth. Commun., 1999, vol. 29, p. 3561.

    Google Scholar 

  266. Japan Patent 2732, 1990; Ref. Zh. Khim., 1991, 7 O 57P.

Download references

Author information

Authors and Affiliations

  1. Lugansk State Pedagogical University, Lugansk, 91011, Ukraine

    V. D. Dyachenko & R. P. Tkachev

Authors
  1. V. D. Dyachenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. P. Tkachev
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dyachenko, V.D., Tkachev, R.P. Functionally-substituted Alkoxyethylenes in Reactions with Nucleophiles. Part I. Synthesis of Six-membered Heterocycles. Russian Journal of Organic Chemistry 39, 757–793 (2003). https://doi.org/10.1023/B:RUJO.0000003153.20325.22

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUJO.0000003153.20325.22

Keywords

Search

Navigation