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Furan and Thiophene Oximes: Synthesis, Reactions, and Biological Activity. (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data on methods for the production of furan and thiophene aldoximes, ketoximes, and amidoximes and their reactions are reviewed. The synthesis of new heterocycles from furan and thiophene oximes and the biological activity of derivatives of the oximes are discussed individually.

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REFERENCES

  1. G. Ocskay and L. Vargha, Tetrahedron, 2, 140 (1958).

    Google Scholar 

  2. K. Ishikawa, Nippon Kagaku Zasshi, 81, 140 (1960).

    Google Scholar 

  3. N. I. Putokhin and V. S. Egorova, Zh. Obshch. Khim., 18, 1866 (1948).

    Google Scholar 

  4. Z. N. Nazarova and O. A. Chuprunova, Zh. Obshch. Khim., 30, 2825 (1960).

    Google Scholar 

  5. V. M. Clark, B. I. Gregory, and G. B. Webb, Ger. Pat. No. 2407909; Chem. Abstr., 81, 1694 31 (1974). 163

    Google Scholar 

  6. S. Jordan, R. E. Markwell, and B. S. Woolcott, J. Chem. Soc. Perkin Trans. 1, 928 (1978).

    Google Scholar 

  7. N. G. Panchenko and V. A. Slavinskaya, Khim. Geterotsikl. Soedin., 1266 (1998).

  8. S. A. Reed, C. V. Banks, and H. Diehl, J. Org. Chem., 12, 792 (1947).

    Google Scholar 

  9. Aktieselkabet Sadolin and Holmblad, Dan. Pat. No. 80973; Chem. Abstr., 50, 14811 (1956).

    Google Scholar 

  10. Sankyo Chemical Industries Co. Ltd., Jpn. Pat. No. 5935 (1964); Chem. Abstr., 61, 13283 (1964).

    Google Scholar 

  11. N. Saldabols, L. N. Alekseeva, S. Hillers, and A. Cimanis, USSR Inventor's Certificate No. 486669; Chem. Abstr., 84, 1645 95 (1976).

    Google Scholar 

  12. T. L. Gilchrist and T. G. Roberts, J. Chem. Soc. Chem. Commun., 847 (1978).

  13. E. Dumez, J. Rodriguez, and J. P. Dulcere, Chem. Commun., 2009 (1999).

  14. T. Severin, P. Adhikary, and I. Schnabel, Chem. Ber., 102, 1325 (1969).

    Google Scholar 

  15. H. K. Kim and P. M. Weintraub, J. Org. Chem., 35, 4282 (1970).

    Google Scholar 

  16. E. Jedlovska, J. Kovac, A. Piklerova, and P. Zalupsky, Coll. Czech. Chem. Commun., 41, 3085 (1976) (and references cited therein).

    Google Scholar 

  17. R. J. Alaimo, J. E. Gray, and G. M. Klein, US Pat. No. 4332735; Chem. Abstr., 97, 92122 (1982).

    Google Scholar 

  18. N. Saldabol, B. S. Velovich, L. N. Alekseeva, B. Brizga, and L. Kruzmetra, Khim.-Farm. Zh., 3, No. 9, 16 (1969).

    Google Scholar 

  19. N. O. Saldabol, A. Yu. Tsimanis, S. A. Giller, Yu. Yu. Popelis, L. N. Alekseeva, A. Ya. Zile, and A. K. Yalinskaya, Khim.-Farm. Zh., 8, No. 10, 12 (1974).

    Google Scholar 

  20. S. Kanemasa, H. Matsuda, A. Kamimura, and T. Kakinami, Tetrahedron, 56, 1057 (2000).

    Google Scholar 

  21. H. B. Snyder, Jr., F. F. Ebetino, G. Gever, B. F. Stevenson, and A. Winterstein, J. Heterocycl. Chem., 7, 959 (1970).

    Google Scholar 

  22. F. Eloy and R. Leaners, Chem. Rev., 62, 155 (1962).

    Google Scholar 

  23. R. W. Henn, B. D. Wilson, and P. E. Woodgate, US Pat. No. 3794488; Chem. Abstr., 81, 71062 (1974).

    Google Scholar 

  24. G. A. Pearse, Chem. Br., 20, 30 (1984); Chem. Abstr., 100, 174565 (1984).

    Google Scholar 

  25. M. von Esch and W. R. Sherman, US Pat. No. 3097214; Chem. Abstr., 59, 13950 (1963).

    Google Scholar 

  26. N. Saldabol, V. Slavinskaya, J. Popelis, and I. Mazheika, Khim. Geterotsikl. Soedin., 168 (2000).

  27. F. Floy and C. J. Mirocha, US Pat. No. 1347874; Chem. Abstr., 68, 87139 (1968).

    Google Scholar 

  28. D. A. Patrick, J. E. Hall, B. C. Bender, D. R. McCurdy, W. D. Wilson, F. A. Tanious, S. Saha, and R. R. Tidwell, Eur. J. Med. Chem., 34, 575 (1999).

    Google Scholar 

  29. S. Wang, J. E. Hall, F. A. Tanious,, W. D. Wilson, D. A. Patrick, D. R. McCurdy, B. C. Bender, and R. R. Tidwell, J. Med. Chem., 34, 215 (1999).

    Google Scholar 

  30. A. Areschka and M. Descamps, British Patent No. 1508210; Chem. Abstr., 89, 1633 90 (1978).

    Google Scholar 

  31. T. Sasaki and T. Yoshioka, Bull. Chem. Soc. Japan, 40, 2604 (1967).

    Google Scholar 

  32. T. Sasaki and T. Yoshioka, Bull. Chem. Soc. Japan, 42, 556 (1969).

    Google Scholar 

  33. N. P. Kostyuchenko, A. F. Oleinik, T. I. Vozyakova, K. Yu. Novitskii, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., 312 (1974).

  34. Yu. Yu. Popelis, E. E. Liepin'sh, and E. Ya. Lukevits, Khim. Geterotsikl. Soedin., 1172 (1985).

  35. P. P. Solov'eva, Yu. N. Sheinker, A. F. Oleinik, and K. Yu. Novitskii, Khim. Geterotsikl. Soedin., 890 (1975).

  36. E. E. Liepin'sh and N. O. Saldabol, Zh. Org. Khim., 27, 521 (1981).

    Google Scholar 

  37. R. Wasylishen and T. Schaefer, Can. J. Chem., 50, 274 (1972).

    Google Scholar 

  38. L. B. Krivdin, G. A. Kalabin, R. A. Nesterenko, R. N. Nesterenko, and B. A. Trofimov, Khim. Geterotsikl. Soedin., 709 (1985).

  39. S. Conde, C. Corral, and J. Lissavetzky, J. Heterocycl. Chem., 22, 301 (1985).

    Google Scholar 

  40. B. Oussaid, J. P. Fayet, G. Pelletier, and B. Garrigues, Bull. Soc. Chim. Belg., 101, 969 (1992).

    Google Scholar 

  41. N. O. Saldabol, V. A. Slavinskaya, E. E. Liepin'sh, Yu. Yu. Popelis, and I. B. Mazheika, Khim. Geterotsikl. Soedin., 1619 (1999).

  42. R. F. Raffauf, J. Am. Chem. Soc., 68, 1765 (1946).

    Google Scholar 

  43. N. Tyutyulkov and D. Panaiotova, Compt. Rend. Acad. Bulg. Sci., 11, 201 (1958); Chem. Abstr., 53, 14781 (1959).

    Google Scholar 

  44. M. Mathew and G. J. Palenik, J. Chem. Soc. Perkin Trans. 2, 1033 (1972).

    Google Scholar 

  45. A. Bryson and F. P. Dwyer, J. Proc. Roy. Soc. N. S. Wales, 74, 240 (1940); Chem. Abstr.,35, 3250 (1941).

    Google Scholar 

  46. R. Katritzky and J. M. Lagowski, J. Chem. Soc., 657 (1959).

  47. G. Schay, Gy. Varsanyi, and F. Dullien, Acta Chim. Acad. Sci. Hung., 15, 273 (1958).

    Google Scholar 

  48. F. Dullien, Can. J. Chem., 35, 1366 (1957).

    Google Scholar 

  49. K. E. Calderbank and R. J. W. Le Fevre, J. Chem. Soc., 1462 (1949).

  50. I. Mazeika, M. Gavars, A. P. Gaukhman, E. Abele, M. Shimanska, and E. Lukevics, Latv. J. Chem., No. 1-2, 89 (1995).

  51. A. van Z orge, Eur. Pat. 7679; Chem. Abstr., 93, 150119 (1980).

    Google Scholar 

  52. S. E. Korostova, L. N. Sobenina, A. I. Mikhaleva, R. N. Nesterenko, S. G. Shevchenko, V. B. Modonov, and R. I. Polovnikova, Zh. Org. Khim., 24, 2538 (1988).

    Google Scholar 

  53. F. Dalmas, M. Gasquet, P. Timon-David, N. Madadi. P. Vanelle, A. Vaille, and J. Maldonado, Eur. J. Med. Chem., 28, 23 (1993).

    Google Scholar 

  54. G. Ulrich and W. Raether, Ger. Pat. No. 2439629; Chem. Abstr., 85, 21082 (1976).

    Google Scholar 

  55. M. Alvarez, R. Granados, D. Mauleon, C. Minguillon, and M. Perez, An. Quim. Ser. C, 80, 258 (1984).

    Google Scholar 

  56. R. Granados, D. Mauleon, and M. Perez, An. Quim. Ser. C, 79, 275 (1983).

    Google Scholar 

  57. E. Abele, Yu. Polelis, E. Lukevits, M. Shimanska, and Yu. Gol'dberg, Khim. Geterotsikl. Soedin., 18 (1994).

  58. E. Abele, K. Rubina, R. Abele, J. Popelis, and E. Lukevits, Latv. J. Chem., No. 3, 59 (1999).

  59. S. J. Kirsch and H. Schelling, J. Org. Chem., 44, 3970 (1979).

    Google Scholar 

  60. E. Abele, R. Abele, K. Rubina, J. Popelis, I. Sleiksa, and E. Lukevics, Synth. Commun., 28, 2621 (1998).

    Google Scholar 

  61. B. A. Trofimov, A. I. Trofimov, A. I. Mikhaleva, R. N. Nesterenko, G. A. Kalabin, and O. A. Tarasova, Zh. Org. Khim., 24, 2618 (1988).

    Google Scholar 

  62. U. Pindur and B. Unterhalt, Arch. Pharm. (Weinheim), 312, 282 (1979).

    Google Scholar 

  63. H. Goda, M. Sato, H. Ihara, and C. Hirayama, Synthesis, 849 (1992).

  64. E. Abele, R. Abele, J. Popelis, and E. Lukevics, Org. Prep. Proc. Int., 32, 153 (2000).

    Google Scholar 

  65. E. Ya. Lukevits and M. G. Voronkov, Khim. Geterotsikl. Soedin., 6 (1965).

  66. E. Lukevics, M. Dzintara, and O. A. Pudova, Zh. Obshch. Khim., 53, 2054 (1983).

    Google Scholar 

  67. E. Abele, K. Rubina, and E. Lukevics, Latv. J. Chem., No. 1, 77 (2000).

  68. Y. Kita, F. Iyoh, O. Tamura, Y. Y. Ke, T. Miki, and Y. Tamura, Chem. Pharm. Bull., 37, 1446 (1989).

    Google Scholar 

  69. S. S. Pelosi, Jr., US Pat. No. 3946049; Chem. Abstr., 85, 21083 (1976).

    Google Scholar 

  70. D. Farge, J. Leboul, Y. Le Goff, and G. Poiget, Ger. Pat. No. 2640484; Chem. Abstr., 87, 39141 (1977).

    Google Scholar 

  71. L. Vargha and F. Gonczy, J. Am. Chem. Soc., 72, 2738 (1950).

    Google Scholar 

  72. L. Vargha and G. Ocskay, Acta Chim. Acad. Sci. Hung., 19, 143 (1959) (and references cited therein).

    Google Scholar 

  73. P. Sohar, G. Varsanyi, L. Vargha, and G. Ocskay, Acta Chim. Acad. Sci. Hung., 40, 431, (1964).

    Google Scholar 

  74. L. Lang, G. Horvath, L. Vargha, and G. Ocskay, Bull. Soc. Chim. France, 2724 (1965).

  75. T. Goto and S. Sakawa, European Patent No.136640; Chem. Abstr., 103, 22474 (1985).

    Google Scholar 

  76. A. F. Oleinik, T. I. Vozyakova, N. I. Solov'eva, and K. Yu. Novitskii, Khim. Geterotsikl. Soedin., 1026 (1975).

  77. E. Abele, Yu. Popelis, M. Gavars, A. Gaukhman, M. Shimanska, and E. Lukevits, Khim. Geterotsikl. Soedin., 886 (1994).

  78. E. Abele, R. Abele, J. Popelis, and E. Lukevics, Latv. J. Chem., No. 2, 61 (1998).

  79. A. Krutosikova, V. Konecny, J. Kovac, and Spirkova, Coll. Czech. Chem. Commun., 40, 313 (1975).

    Google Scholar 

  80. T. Sasaki and T. Yoshioka, Yuki Gosei Kagaku Kyokai Shi, 25, 665 (1967); Chem. Abstr., 68, 12789 (1968).

    Google Scholar 

  81. I. Castro, E. Lukevits, R. Pastrana, M. D. Gonzalez, and D. Popelis, Sobre Deriv. Cana Azucar, 18, 36 (1984); Chem. Abstr.,104, 224792 (1986).

    Google Scholar 

  82. Yu. S. Andreichuk, D. D. Nekrasov, E. A. Kolevatova, and M. A. Trushule, Khim.-Farm. Zh., 24, 33 (1990).

    Google Scholar 

  83. M. von Eisch and A. J. Crovetti, US Pat. No. 3272833; Chem. Abstr., 66, 37761 (1967).

    Google Scholar 

  84. E. Abele and E. Lukevics, Org. Prep. Proc. Int., 32, 235 (2000).

    Google Scholar 

  85. B. P. Fabrichnyi, S. M. Kostrova, G. P. Gromova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., 1483 (1973).

  86. D. Mullem and L. Shuttleworth, UK Patent No. 2092128; Chem. Abstr., 98, 53678 (1983).

    Google Scholar 

  87. E. Abele, R. Abele, K. Rubina, Yu. Popelis, A. Gaukhman, and E. Lukevits, Khim. Geterotsikl. Soedin., 1325 (1998).

  88. E. Abele, K. Rubina, R. Abele, A. Gaukhman, and E. Lukevits, J. Chem. Res. (S), 618 (1998).

  89. D. J. Ager, Tetrahedron Lett., 24, 5441 (1983).

    Google Scholar 

  90. D. J. Ager, J. Chem. Res. (S), 237 (1985).

  91. W. Zhao, Huahue Shiji, 19, 273 (1997); Chem. Abstr.,127, 330917 (1997).

    Google Scholar 

  92. H. Migulla and H. Paul, East Ger. Pat. No. 130148; Chem. Abstr., 91, 39306 (1979).

    Google Scholar 

  93. R. Cho, N. S. Cho, S. H. Song, and S. K. Lee, J. Org. Chem., 63, 8304 (1999).

    Google Scholar 

  94. S. Morikawa and S. Teratake, Jap. Pat. No. 7919963; Chem. Abstr., 91, 39301 (1979).

    Google Scholar 

  95. A. Obregia and C. V. Gheorghiu, J. Prakt. Chem., 128, 239 (1930); Chem. Abstr.,25, 1506 (1931).

    Google Scholar 

  96. E. Abele, R. Abele, and E. Lukevics, Latv. J. Chem., No. 3, 63 (1999).

  97. L. Beregi, Magyar Kem. Folyoirat, 56, 257 (1950); Chem. Abstr.,46, 8000 (1952).

    Google Scholar 

  98. W. Reeve and J. Christian, J. Am. Chem. Soc., 78, 860 (1956).

    Google Scholar 

  99. G. S. Wayne, G. S. Lannoye, A. R. Haight, S. L. Parekh, W. Zhang, and R. R. Copp, Heterocycles, 53, 1175 (2000).

    Google Scholar 

  100. S. Demir, Pure Appl. Chem., 69, 105 (1997).

    Google Scholar 

  101. Q. H. Chen, X. Z. Yu, T. Y. Zhang, and Z. B. Jia, Acta Chim. Sinica. Engl. Ed., 176 (1989).

  102. D. Nenitescu and C. Bucur, Ger. Pat. No. 1048590; Chem. Abstr., 55, 3614 (1961).

    Google Scholar 

  103. Z. Rybakow and J. Lange, Polish Patent No. 42394; Chem. Abstr., 55, 6496 (1961).

    Google Scholar 

  104. A. Swirska and J. Lange, Polish Patent No. 42189; Chem. Abstr., 55, 5533 (1961).

    Google Scholar 

  105. H. Ogawa and H. Sakaichi, Synthesis, 138 (1972).

  106. L, Vargha and G. Ocskey, Tetrahedron, 2, 151 (1958).

    Google Scholar 

  107. B. B. Greene and K. G. Lewis, Tetrahedron Lett., 4759 (1966).

  108. B. B. Greene and K. G. Lewis, Aust. J. Chem., 21, 1845 (1968).

    Google Scholar 

  109. Ssah. Chemical Industry Co. Ltd., Jpn. Pat. No. 81133285; Chem. Abstr., 96, 162708 (1982).

    Google Scholar 

  110. E. Abele and E. Lukevics, Heterocycles, 53, 2285 (2000).

    Google Scholar 

  111. B. A. Trofimov, Adv. Heterocycl. Chem., 51, 177 (1990).

    Google Scholar 

  112. B. A. Trofimov and A. I. Mikhaleva, Heterocycles, 37, 1193 (1994).

    Google Scholar 

  113. B. A. Trofimov and A. I. Mikhaleva, Zh. Org. Khim., 32, 1127 (1996).

    Google Scholar 

  114. B. A. Trofimov, Pyrroles. Part Two: The Synthesis, Reactivity and Physical Properties of Substituted Pyrroles(Ed. A. Jones), Wiley, New York (1992), p. 131.

    Google Scholar 

  115. S. E. Korostova, A. I. Mikhalev, and B. A. Trofimov, Usp. Khim., 68, 506 (1999).

    Google Scholar 

  116. G. A. Pinna, M. A. Pirisi, and G. Paglietti, J. Chem. Res. (S), 210 (1993).

  117. S. E. Korostova, R. N. Nesterenko, A. I. Mikhaleva, R. I. Polovnikova, and N. I. Golovanova, Khim. Geterotsikl. Soedin., 901 (1989).

  118. A. Krutosikova, J. Kovac, M. Dandarova, and M. Valenty, Coll. Czech. Chem. Commun., 43, 288 (1978).

    Google Scholar 

  119. R. S. Kusurkar, M. S. Wadia, D. K. Bhosale, S. S. Tavale, and V. G. Puranik, J. Chem. Res. (S), 478 (1996). 166

    Google Scholar 

  120. T. Sasaki, T. Yoshioka, and Y. Suzuki, Yuki Gosei Kagaku Kyokai Shi, 27, 998 (1969); Chem. Abstr.,72, 43542 (1970).

    Google Scholar 

  121. R. and L. Molecular Research Ltd., French Patent No. 2085655 (1972); Chem. Abstr., 77, 88474 (1972).

    Google Scholar 

  122. H. Hishmat, K. M. Khalil, N. M. A. El-Ebrashi, and M. N. M. Khodeir, Z. Naturforsch., 33B, 1491 (1978).

    Google Scholar 

  123. P. Demerseman, G. Colin, J. P. Lechartier, A. Cheutin, S. Combrisson, and R. Royer, Bull. Soc. Chim. France, 3601 (1969).

  124. P. Dubus, B. Decroix, and P. Pastour, Ann. Chim. (Paris), 10, 331, (1975).

    Google Scholar 

  125. V. L. Narayanan, US Pat. No. 3976657; Chem. Abstr., 85, 192742 (1976).

    Google Scholar 

  126. A. A. Avetisiyan, G. S. Melikyan, and A. V. Galstiyan, Arm. Zh. Khim., 36, 738 (1983).

    Google Scholar 

  127. M. Descamps and A. Areschka, Ger. Pat. No. 2657902; Chem. Abstr., 87, 167874 (1977).

    Google Scholar 

  128. I. Saikawa, Jpn. Pat. No. 2822 (1967); Chem. Abstr., 66, 115715 (1967).

    Google Scholar 

  129. B. Uossaid, L. Moeini, B. Martin, D. Villemin, and B. Garrigues, Synth. Commun., 25, 1451 (1995).

    Google Scholar 

  130. S. Kusurkar and D. K. Bhosale, Tetrahedron Lett., 32, 3199 (1991) (and references therein).

    Google Scholar 

  131. C. L. Hickson and H. McNab, Synthesis, 464 (1981).

  132. J. Fortea, J. Prakt. Chem., 317, 705 (1975).

    Google Scholar 

  133. M. M. Krayushkin, M. A. Kalik, E. Yu. Zvezdina, and V. S. Bogdanov, Izv. Akad. Nauk. SSSR. Ser. Khim., 2837 (1991).

  134. M. M. Krayushkin, M. A. Kalik, E. Yu. Zvezdina, L. G. Vorontsova, and M. G. Kurella, Mendeleev Commun., 114 (1993).

  135. C. Tsuchiya, Nippon Kagaku Zasshi, 82, 1549 (1961); Chem. Abstr.,59, 2752 (1963).

    Google Scholar 

  136. O. Meth-Cohn and B. Narine, Synthesis, 133 (1980).

  137. B. Unterhalt and H. J. Reinhold, Arch. Pharm. (Weinheim), 308, 346 (1975).

    Google Scholar 

  138. S. Deprets and G. Kitsch, Eur. J. Org. Chem., 1353 (2000).

  139. A. Bryson and F. P. Dwyer, J. Proc. Roy. Soc. N. S. Wales, 74, 471 (1941); Chem. Abstr.,35, 4768 (1941).

    Google Scholar 

  140. J. Cymerman Craig and A. R. Naik, J. Am. Chem. Soc., 84, 3410 (1962).

    Google Scholar 

  141. A. Buzas and J. Teste, Bull. Soc. Chim. France, 359 (1960).

  142. H. Cho, K. Murakami, H. Nakanishi, H. Isoshima, K. Hayakawa, and I. Uchida, Heterocycles, 48, 919 (1998).

    Google Scholar 

  143. R. Martinez, M. E. L. Duran, C. L. Cortes, and J. Z. Gustavo Avila, J. Heterocycl. Chem., 36, 687 (1999).

    Google Scholar 

  144. R. Neidlein and N. Kolb, Arch. Pharm. (Weinheim), 312, 397 (1979).

    Google Scholar 

  145. B. P. Fabrichnyi, I. F. Shalavina, and Ya. V. Gol'dfarb, Zh. Obshch. Khim., 31, 1244 (1961).

    Google Scholar 

  146. V. P. Fabrichnyi, V. N. Bulgakova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., 483 (1985).

  147. M. Bastian, A. Ebnother, and E. Jucker, Helv. Chim. Acta, 34, 283 (1971).

    Google Scholar 

  148. A. P. Stankyavichus, J. M. M. Stankyavichene, and P. B. Terent'ev, Khim. Geterotsikl. Soedin., 1462 (1999).

  149. P. Bessin, J. Laforest, and G. Thuillier, US Pat. No. 4207319; Chem. Abstr., 93, 220574 (1980).

    Google Scholar 

  150. G. Thuillier, J. Laforest, and P. Bessin, Ger. Pat. No. 2449205; Chem. Abstr., 83, 97004 (1975).

    Google Scholar 

  151. J. Laforest, Ger. Pat. No. 2922799; Chem. Abstr., 93, 1809 89; Chem. Abstr., 92, 180989 (1980).

    Google Scholar 

  152. J. Engel, A. Kleeman, F. Stroman, and K. Thiemer, Ger. Pat. No. 2851387; Chem. Abstr., 91, 74460 (1979).

    Google Scholar 

  153. J. Laforest, J. Bonnet, and P. Bessin, Ger. Pat. No. 2804981; Chem. Abstr., 89, 1973 23 (1978).

    Google Scholar 

  154. M. Varache-Lembege, A. Nuhrich, P. Renard, F. Duboudin, J. Vercauteren, and G. Devaux, Arch. Pharm. (Weinheim), 328, 417 (1995).

    Google Scholar 

  155. V. Philips' Gloeilampenfabrieken, Netherlands Patent No. 6810133; Chem. Abstr., 72, 121354 (1970).

    Google Scholar 

  156. L. A. Pons, M. F. Rodda, R. H. P. Marcy, and D. C. J. Duval, Ger. Pat. No. 2042504; Chem. Abstr., 74, 125485 (1971).

    Google Scholar 

  157. J. S. Knutsen K. E. Andersen, J. Lau, B. F. Lundt, R. F. Henry, H. E. Morton, L. Naerum, H. Peterson, H. Stephenson, P. D. Suzdak, M. D. B. Swedberg, C. Thomsen, and P. E. Sorensen, J. Med. Chem., 42, 3447 (1999).

    Google Scholar 

  158. J. van Dijk and J. M. A. Zwagemakers, Ger. Pat. No. 20 1605 7; Chem. Abstr., 74, 12990 (1971).

    Google Scholar 

  159. Sankyo Co. Ltd., Jpn. Pat. No. 5970685; Chem. Abstr., 101, 110722 (1984).

    Google Scholar 

  160. J. P. Riffaud, C. Dupont, L. Rene, and R. Royer, Eur. J. Med. Chem.-Chim. Ther., 17, 577 (1982).

    Google Scholar 

  161. R. Shridhar, C. V. Reddy Sastry, S. C. Chaturvedi, R. Gurumurthy, P. P. Singh, C. Seshagiri Rao, and A. Y. Junnarkar, Indian J. Chem., 23B, 692 (1984).

    Google Scholar 

  162. H. Hall, K. F. Bastow, A. E. Warren, C. R. Barnes, and G. M. Bouet, Appl. Organomet. Chem., 13, 819 (1999).

    Google Scholar 

  163. H. Hall, C. C. Lee, G. Ibrahim, M. A. Khan, and G. M. Bouet, Appl. Organomet. Chem., 11, 565 (1997).

    Google Scholar 

  164. K. Matsumura, O. Miyashita, H. Shimadzu, and N. Hashimoto, Ger. Pat. No. 2841379; Chem. Abstr., 91, 39519 (1979).

    Google Scholar 

  165. W. G. Brouwer, Canadian Patent No. 2 1631 75; Chem. Abstr., 125, 221559 (1996).

    Google Scholar 

  166. J. R. Nicolaus and E. Testa, British Patent No. 964721; Chem. Abstr., 61, 9467 (1964).

    Google Scholar 

  167. T. Sasaki, Jpn. Pat. No. 692722; Chem. Abstr., 72, 78854 (1970).

    Google Scholar 

  168. S. Ueno, E. Shimogo, T. Kawasaki, D. Immaru, and Y. Ossaka, Jpn. Pat. No. 7135064; Chem. Abstr., 76, 3711 (1972).

    Google Scholar 

  169. L. Kistaludy, L. Dancsi, A. Patthy, G. Fekete, and I. Szabo, Canadian Patent No. 1058195; Chem. Abstr., 92, 6399 (1980).

    Google Scholar 

  170. M. von Esch and A. J. Crovetti, US Pat. No. 3272828; Chem. Abstr., 65, 18560 (1966).

    Google Scholar 

  171. A. M. von Esch and A. J. Crovetti, US Pat. No. 3660390; Chem. Abstr., 77,6 1794 (1972).

    Google Scholar 

  172. I. Saiwaka and T. Wada, Jpn. Pat. No. 9334 (1967); Chem. Abstr., 68, 95663 (1968).

    Google Scholar 

  173. I. Saiwaka and T. Wada, Jpn. Pat. No. 9335 (1967); Chem. Abstr., 68, 95664 (1968).

    Google Scholar 

  174. Norwich Pharmacal Co., Netherlands Patent No. 6500124; Chem. Abstr., 64, 8135 (1966).

    Google Scholar 

  175. G. Leandri, L. Maioli, and L. Ruzzier, Boll. Sci. Fac. Chim. Ind. Bologna, 15, 57 (1957); Chem. Abstr., 52, 7291 (1958).

    Google Scholar 

  176. A. Kotani and S. Inamasu, Jpn. Pat. No. 7535113; Chem. Abstr., 83, 193063 (1975).

    Google Scholar 

  177. C. Seoh, Yakhak Hoeji, 17, 167 (1973); Chem. Abstr., 81, 151867 (1974).

    Google Scholar 

  178. A. J. Crovetti and R. G. Stein, US Pat. No. 4061764; Chem. Abstr., 88, 100348 (1977).

    Google Scholar 

  179. S. N. Maiti, E. L. Setti, O. A. Phillips, A. V. N. Reddy, R. G. Micetich, R. Singh, F. Higastani, C. Kunugita, K. Nishida, and T. Uji, PCT Int. Appl. WO 9847895; Chem. Abstr., 129,3 16092 (1998).

    Google Scholar 

  180. U. Heinemann, and S. Dutzmann, Ger. Pat. No. 19622354; Chem. Abstr., 128, 61422 (1998).

    Google Scholar 

  181. C. Humber, Ger. Pat. No. 2537558; Chem. Abstr., 84, 180253 (1976).

    Google Scholar 

  182. I. Gregory and D. M. Rogers, Ger. Pat. No. 2627212; Chem. Abstr., 86, 171478 (1977).

    Google Scholar 

  183. E. Ayres, Ger. Pat. No. 2744135; Chem. Abstr., 89, 43460 (1978).

    Google Scholar 

  184. H. O'Callaghan and M. Gregson, Ger. Pat. No. 2835288; Chem. Abstr., 90, 186982 (1979).

    Google Scholar 

  185. W. Foxton A. J. Pine, and G. B. Webb, UK Patent No. 2029823; Chem. Abstr., 93, 186382 (1980).

    Google Scholar 

  186. Biochemica Opos S. r. l., Jpn. Pat. No. 58 1675 93; Chem. Abstr., 100, 138847 (1984).

    Google Scholar 

  187. K. H. Lee, Y. J. Yun, and K. D. Choe, China Patent No.1 1997 53; Chem. Abstr., 132, 279057 (2000).

    Google Scholar 

  188. D. Greenwood, N. J. Pearson, and F. O'Grady, J. Antimicrob. Chemother., 2, 337 (1976).

    Google Scholar 

  189. S. Lee, C. Sun, and H. P. Wang, Chin. Pharm. J., 49, 195 (1997).

    Google Scholar 

  190. T. Kay, British Patent No. 1273357; Chem. Abstr., 77,6 1803 (1972).

    Google Scholar 

  191. T. Kay, S. African Patent No. 6907157; Chem. Abstr., 76, 14328 (1972).

    Google Scholar 

  192. S. Kishikawa, S. Maekawa, K. Matsui, and I. Aoshima, Jpn. Pat. No. 7502733; Chem. Abstr., 83, 73524 (1975).

    Google Scholar 

  193. E. Jedlovska, J. Kovak, A. Piklerova, and V. Konecny, Chem. Zvesti, 29, 703 (1975).

    Google Scholar 

  194. R. G. Stein, A. J. Crovetti, and T. L. Crouch, Ger. Pat. No. 2262189; Chem. Abstr., 79, 66160 (1973).

    Google Scholar 

  195. J. Drabek, Z. Vesela, T. Sirota, J. Obertas, and M. Rupcik, Czech. Patent No. 141927; Chem. Abstr., 77, 88278 (1972).

    Google Scholar 

  196. Z. Vasela and S. Trchlik, Czech. Patent No. 152838; Chem. Abstr., 81, 105264 (1974).

    Google Scholar 

  197. T. Nishioka, A. Maehara, T. Mizutani, N. Itaya, I. Nakayama, and M. Hirao, Jpn. Pat. No. 8017323; Chem. Abstr., 93, 46404 (1980).

    Google Scholar 

  198. J. Bull, Ger. Pat. No. 2919816; Chem. Abstr., 92, 76273 (1980).

    Google Scholar 

  199. K. Murata and N. Kiriyama, Rept. Osaka Municipal Research Inst. Domestic Sci., 17, 195 (1946); Chem. Abstr., 41, 4790 (1947).

    Google Scholar 

  200. R. J. Alaimo and J. E. Gray, US Pat. No. 4336199; Chem. Abstr., 144752 (1982).

  201. R. J. Alaimo and J. E. Gray, US Pat. No. 4339386; Chem. Abstr., 97, 1821 97 (1982).

    Google Scholar 

  202. V. Konecny and A. Krutosikova, Czech. Patent No. 169548; Chem. Abstr., 88, 169943 (1978).

    Google Scholar 

  203. J. Perronet and P. Girault, Ger. Pat. No. 2355424; Chem. Abstr., 81, 91334 (1974).

    Google Scholar 

  204. H. Suzuki, T. Mita, T. Takeyama, M. Hanaue, M. Nishikubo, and K. Yamagishi, Jpn. Pat. No. 02250869; Chem. Abstr., 114,10 1988 (1991).

    Google Scholar 

  205. T. Kay, British Patent No. 1245397; Chem. Abstr., 75, 129654 (1971).

    Google Scholar 

  206. T. Kay, S. African Patent No. 7100299; Chem. Abstr., 76, 153578 (1972).

    Google Scholar 

  207. Imperial Chemical Industries Ltd., French Patent No. 2125659; Chem. Abstr., 78, 159411 (1973).

    Google Scholar 

  208. J. Crovetti and R. G. Stein, Ger. Pat. No. 2257062; Chem. Abstr., 79, 42332 (1973).

    Google Scholar 

  209. J. Bull, UK Patent No. 2053188; Chem. Abstr., 95, 80712 (1981).

    Google Scholar 

  210. H. Gayer, P. Gerdes, D. Kuhnt, S. Dutzmann, H. W. Dehne, and G. Haenssler, PCT Int. Appl. WO 9501973; Chem. Abstr., 124, 29591 (1996).

    Google Scholar 

  211. S. Trah and F. Gantz, PCT Int. Appl. WO 9308183; Chem. Abstr., 119, 203277 (1993).

    Google Scholar 

  212. S. Trah, Ger. Pat. No. 1991 4756; Chem. Abstr., 131, 351229 (1999).

    Google Scholar 

  213. D. Farge, J. Leboul, Y. Le Goff, and G. Poiget, Ger. Pat. No. 283 1983; Chem. Abstr., 90, 181591 (1979).

    Google Scholar 

  214. S. A. Philagro, Israeli Patent No. 55228; Chem. Abstr., 99, 1755 84 (1985).

    Google Scholar 

  215. U. Gebert and W. Raether, Ger. Pat. No. 2651084; Chem. Abstr., 90, 152184 (1979).

    Google Scholar 

  216. Hoechst A.G., Jpn. Pat. No. 7859660; Chem. Abstr., 89, 146903 (1978).

    Google Scholar 

  217. U. Gebert and W. Raether, Ger. Pat. No. 2516317; Chem. Abstr., 87, 39261 (1977).

    Google Scholar 

  218. U. Gebert and W. Raether, Ger. Pat. No. 2439629; Chem. Abstr., 85, 21082 (1976).

    Google Scholar 

  219. P. A. Bukowick, US Pat. No. 4002649; Chem. Abstr., 86, 139826 (1977).

    Google Scholar 

  220. H. Martin, US Pat. No. 4451286; Chem. Abstr., 101, 105791 (1984).

    Google Scholar 

  221. C. Rentzea, G. Reissenweber, K. H. Feuerherd, and J. Jung, Ger. Pat. No. 3213373; Chem. Abstr., 100, 68306 (1984).

    Google Scholar 

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Abele, E., Lukevics, E. Furan and Thiophene Oximes: Synthesis, Reactions, and Biological Activity. (Review). Chemistry of Heterocyclic Compounds 37, 141–169 (2001). https://doi.org/10.1023/A:1017559314561

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