5,6-Dihydropyridin-2(1H)-ones and 5,6-dihydropyridine-2(1H)-thiones (review)

Chemistry of Heterocyclic Compounds

Volumn 35, Issue 2, 1999, Pages 125-145

  Fisyuk, A S ^a   Bundel', Yu G ^a  

^a OMSK STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2442486741     PISSN: 00093122     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02251699     Document Type: Review

References (138)

1. S. Takano, M. Sato, and K. Orgasawara, Heterocycles, 16, 799 (1981).
2. Y. Torisawa, M. Nagakawa, T. Hosaka, K. Tanabe, Z. Lai, K. Ogata, T. Nakata, T. Oishi, and T. Hino, J. Org. Chem., 57, 5741 (1992).
3. D. O. Imbroisi and N. S. Simpkins, Tetrahedron Lett., 30, 4309 (1989).
4. D. A. Davis and G. W. Gribble, Tetrahedron Lett., 31, 1081 (1990).
5. E. Wu, T. Shinka, P. Caldera-Munoz, H. Yoshizumi, A. Trevor, and N. Castagnoli, Chem. Res. Toxicol., No. 1, 186 (1988).
6. T. J. Hagen and G. D. Searle, Synlett, No. 1, 63 (1990).
7. D. O. Imbroisi and N. S. Simpkins, J. Chem. Soc. Perkin Trans. I, No. 6, 1815 (1991).
8. T. Varea, M. Dufour, L. Micouin, C. Riche, A. Chiaroni, J.-Ch. Quirion, and H.-P. Husson, Tetrahedron Lett., 36, 1035 (1995).
9. L. Micouin, A. Diez, J. Castells, D. Lopez, M. Rubiralta, J.-Ch. Quirion, and H.-P. Husson, Tetrahedron Lett., 36, 1693 (1995).
10. A. Diez, J. Castells, P. Forns, M. Rubiralta, D. S. Grierson, H. P. Husson, X. Solans, and M. Font-Bardia, Tetrahedron, 50, 6585 (1994).
11. M. Amat, N. Llor, J. Bosch, and X. Solans, Tetrahedron, 53, 719 (1997).
12. Sh. Li, S. Kosemura, and Sh. Yamamura, Tetrahedron Lett., 35, 8217 (1994).
13. Y. Torisawa, M. Nakagawa, H. Takami, T. Nagata, M. A. Ali, and T. Hino, Heterocycles, 39, 277 (1994).
14. M. Ladlow, P. M. Cairns, and Ph. Magnus, J. Chem. Soc. Chem. Commun., No. 24, 1756 (1986).
15. S. G. Sosnicki, T. S. Jagodzinnski, and J. Liebscher, J. Heterocycl. Chem., 34, 643 (1997);
16. Chem. Abs., 127, 50514 (1997).
17. A. S. Fisyuk and M. A. Vorontsova, Khim. Geterotsikl. Soedin., No. 1, 73 (1998).
18. D. L. Comins, X. Chen, and S. P. Joseph, Tetrahedron Lett., 37, 9275 (1996).
19. A. R. Battersby and J. C. Turner, J. Chem. Soc. Perkin Trans. I, No. 4, 717 (1960).
20. S. T. Endo, N. Otake, S. Takeuchi, and H. Yonehara, J. Antibiotics. Ser. A, 17, 172 (1964).
21. Sh. Yamamura, K. Hasegawa, and K. Harada, Japanese Patent No. 05125046; Chem. Abs., 119, 154012 (1993).
22. Sh. Nishiyama, Sh. Yamamura, K. Hasegawa, M. Sakoda, and K. Harada, Tetrahedron Lett., 32, 6753 (1991).
23. A. R. Battersby and J. C. Turner, Chem. Ind., 1324 (1958);
24. Chem. Abs., 53, 9263 (1959).
25. T. Fujii, Sh. Yoshifuji, and M. Ohba, Chem. Pharm. Bull., 26, 645 (1978).
26. B. Alcaide, R. Alajarin, J. Plumet, and J. Rodriguez-Lopez, Synthesis, No. 6, 440 (1988).
27. O. E. Edwards and T. Singh, Can. J. Chem., 32, 683 (1954).
28. B. Kheddis, D. Bahibah, M. Hamdi, and J.-J. Perie, Bull. Soc. chim. France, No. 3-4, 135 (1981).
29. J. J. Plattner, R. D. Gless, and H. Rapoport, J. Am. Chem. Soc., 94, 8613 (1972).
30. S. Tatsuoka, Y. Yeno, K. Tanaka, and T. Ueyanagi, Japanese Patent No. 1321084; Chem. Abs., 59, 10006 (1963).
31. R. G. Glushkov, V. A. Volskova, V. G. Smirnova, and O. Yu. Magidson, Dokl. Akad. Nauk SSSR, 187, 327 (1969).
32. J. W. F. Whitehead, K. Mills, I. H. Coates, A. W. Oxford, and P. Ch. North, European Patent No. 458624; Chem. Abs., 116, 106098 (1992).
33. M. V. Strandtmann, M. P. Cohen, and J. Shavel, J. Med. Chem., 6, 719 (1963);
34. Chem. Abs., 59, 15275 (1963).
35. K. Schweiger, Monatsh. Chem., 114, 581 (1983).
36. G. Zigeuner, W.-B. Lintschinger, A. Fuchsgruber, and K. Kollmann, Monatsh. Chem., 107, 155 (1976).
37. K. Schweiger and G. Zigeuner, Monatsh. Chem., 109, 543 (1978).
38. D. Desmaele, K. Mekouar, and J. d'Angelo, J. Org. Chem., 62, 3890 (1997).
39. I. Iijima, K. Homma, Y. Saiga, Y. Matsuoka, and M. Matsumoto, European Patent No. 149534; Chem. Abs., 104, 19570 (1986).
40. T. Fujii, H. Kogen, Sh. Yoshifuji, and K. Iga, Chem. Pharm. Bull., 27, 1847 (1979).
41. P. Patel and J. A. Joul, J. Chem. Soc. Chem. Commun., No. 15, 1021 (1985).
42. P. Meghani and J. A. Joul, J. Chem. Soc. Perkin Trans. I, No. 1, 1 (1988).
43. S. Mabic and N. Castagnoli, J. Org. Chem., 61, 309 (1996).
44. M. Mori, N. Kanda, I. Oda, and Y. Ban, Tetrahedron, 41, 5465 (1985).
45. Y. Kawashima, M. Sato, Y. Hatada, J. Goto, Y. Nakashima, K. Hatayama, and Sh. Shibuya, Chem. Pharm. Bull., 38, 393 (1990).
46. E. M. Campi, J. M. Chong, W. R. Jackson, and M. B. D. Schoot, Tetrahedron, 50, 2533 (1994).
47. K. Shishido, M. Ito, S. Shimada, K. Fukumoto, and T. Kametami, Chem. Lett., No. 11, 1943 (1984).
48. A. Azzouzi, M. Dufour, J.-C. Gramain, and R. Remuson, Heterocycles, 27, 133 (1988).
49. G. D. Maio and A. Tardella, Gazz. Chim. Ital., 96, 387 (1966);
50. Chem. Abs., 65, 2214 (1966).
51. M. Rubiralta, A. Torrens, and A. Palet, Tetrahedron Lett., 30, 6761 (1989).
52. L. E. Overman, and A. J. Robichaud, J. Am. Chem. Soc., 111, 300 (1989).
53. A. S. Kukharev, I. G. Tishchenko, and V. I. Tyvorskii, Khim. Geterotsikl. Soedin., No. 10, 1313 (1987).
54. H.-J. Altenbach and K. Himmeldirk, Tetrahedron: Asymmetry, 6, 1077 (1995).
55. A. S. Fisyuk, M. A. Vorontsova, A. E. Gatsenko, A. V. Kurilenko, L. S. Epil'dimov, and R. S. Sagitullin, Russian Patent No. 1766917; Byull. Izobr., No. 37 (1992).
56. A. S. Fyssiuk, M. A. Vorontsova, and R. S. Sagitullin, Mendeleev Commun., No. 6, 249 (1993).
57. A. S. Fisyuk, M. A. Vorontsova, and S. A. Ivanov, Khim. Geterotsikl. Soedin., No. 6, 812 (1994).
58. A. S. Fisyuk and M. A. Vorontsova, Khim. Geterotsikl. Soedin., No. 2, 220 (1998).
59. N. Ohba, A. Ikeda, K. Matsunary, Y. Yamada, M. Hirata, Y. Nakamura, A. Takeuchi, and H. Karino, European Patent No. 372586; Chem. Abs., 114, 247145 (1991).
60. Y. Kawamura, E. Oya, K. Itoh, and H. Kita, WO Patent No. 9407857; Chem. Abs., 121, 230667 (1994).
61. A. S. Fissyuk, M. A. Vorontsova, and D. V. Temnikov, Tetrahedron Lett., 37, 5203 (1996).
62. A. S. Fisyuk, L. V. Berdovich, D. V. Temnikov, and L. N. Knyazkova, Khim. Geterotsikl. Soedin., No. 7, 921 (1997).
63. A. S. Fisyuk and M. A. Vorontsova, Khim. Geterotsikl. Soedin., No. 6, 723 (1998).
64. A. S. Fisyuk, N. V. Poendaev, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 2, 281 (1998).
65. E. Schmitz, R. Urban, G. Zimmermann, E. Grundemann, and G. Benndorf, Z. Chem., 12, 100 (1972).
66. G. B. Gill, G. Pattenden, and S. J. Reynolds, Tetrahedron Lett., 30, 3229 (1989).
67. G. B. Gill, G. Pattenden, and S. J. Reynolds, J. Chem. Soc. Perkin Trans. I, No. 4, 369 (1994).
68. M. Mori, Y. Washioka, T. Urayama, K. Yoshiura, K. Chiba, and Y. Ban, J. Org. Chem., 48, 4058 (1983).
69. Ch. Coperet, T. Sugihara, and E. Negishi, Tetrahedron Lett., 36, 1771 (1995).
70. Ch. M. Marson, U. Grabowska, and T. Walsgrove, J. Org. Chem., 57, 5045 (1992).
71. Ch. M. Marson, U. Grabowska, A. Fallah, T. Walsgrove, D. S. Eggleston, and P. W. Baures, J. Org. Chem., 59, 291 (1994).
72. E. Fischer and K. Raske, Ber., 37, 3607 (1905).
73. M. Shamma and P. D. Rosenstock, J. Org. Chem., 26, 718 (1961).
74. A. J. Verbiscar and K. N. Campbell, J. Org. Chem., 29, 2472 (1964).
75. P. M. Boll, J. Hansen, O. Simonsen, and N. Thorup, Tetrahedron, 40, 171 (1984).
76. H. Alper and J. T. Edward, J. Org. Chem., 32, 2938 (1967).
77. M. Sekiya and Y. Watase, Japanese Patent No. 7970238; Chem. Abs., 91, 175207 (1979).
78. M. M. Midland and J. I. McLoughlin, Tetrahedron Lett., 29, 4653 (1988).
79. H. Waldmann, M. Braun, and M. Drager, Angew. Chem., Int. Ed., 29, 1468 (1990).
80. H. Waldmann, M. Braun, and M. Drager, Tetrahedron: Asymmetry, 2, 1231 (1991).
81. M. M. Midland and R. W. Koops, J. Org. Chem., 57, 1158 (1992).
82. R. Lock and H. Waldmann, Lieb. Ann. Chem., No. 5, 511 (1994).
83. S. M. Brandstadter, I. Ojima, and K. Hirai, Tetrahedron Lett., 28, 613 (1987).
84. Ts. P. Cholakova and Kh. Ivanov, Khim. Geterotsikl. Soedin., No. 2, 209 (1988).
85. A. L. Borgi, M. Bellassoued, and J.-L. Moreau, Compt. Rend. Acad. Paris, 307, 1805 (1988).
86. J. H. Bateson, A. M. Quinn, T. C. Smale, and R. Southgate, J. Chem. Soc. Perkin Trans. I, No. 11, 2219 (1985).
87. I. Guareschi, Ber., 26, 450 (1893).
88. E. Cavalieri and D. Gravel, Can. J. Chem., 48, 2727 (1970).
89. H. Kuehnis, R. Denss, and C. H. Eugster, Swiss Patent No. 417591; Chem. Abs., 68, 39482 (1968).
90. C. H. Eugster, L. Leichner, and E. Jenny, Helv. Chim. Acta, 46, 543 (1963).
91. C. Barat, J. Indian Chem. Soc., 7, 321 (1930).
92. U. Basu, J. Indian Chem. Soc., 8, 119 (1931).
93. H. Fiesselmann and W. Ehmann, Chem. Ber., 91, 1706 (1958).
94. A. Sakurai and H. Midorikawa, Bull. Chem. Soc. Jpn., 40, 1680 (1967).
95. Z. A. Bomika, M. B. Andaburskaya, Yu. E. Pelcher, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 8, 1108 (1975).
96. J. Kuthan, P. Nesvadba, Z. Donnerova, and P. Trska, Coll. Czech. Chem. Commun., 42, 2152 (1977).
97. N. R. El-Rayyes and F. H. Al-Hajjar, J. Heterocyclic Chem., 21, 1473 (1984).
98. M. Komatsu, Sh. Yamamoto, Y. Ohshiro, and T. Agawa, Tetrahedron Lett., 22, 3769 (1981).
99. G. V. Grishina, S. O. Bachurin, S. E. Tkachenko, and N. S. Zefirov, Khim. Geterotsikl. Soedin., No. 7, 913 (1993).
100. E. Baggiolini, H. G. Barscheid, G. Bozzato, E. Cavalieri, K. Schaffner, and O. Jeger, Helv. Chim. Acta, 54, 429 (1971).
101. K. Balenovic, H. U. Daniker, R. Goutarel, M. M. Janot, and V. Prelog, Helv. Chim. Acta, No. 307-308, 2519 (1952).
102. C. Herdeis and A. Dimmerling, Heterocycles, 22, 2277 (1984).
103. G. De Nanteuil, A. Ahond, Guilhem, C. Poupat, E. Tran Huu Dau, P. Potier, M. Pusset, J. Pusset, and P. Laboute, Tetrahedron, 41, 6019 (1985).
104. S. A. Fedoreyev, N. K. Utkina, S. G. Ilyin, M. V. Reshetnyak, and O. B. Maximov, Tetrahedron Lett., 27, 3177 (1986).
105. P. A. Clare, Comprehensive Organic Chemistry (Eds. D. Barton and W. D. Ollis) [Russian translation], Vol. 8,
106. Nitrogen-Containing Heterocycles (Ed. P. G. Samms), Khimiya, Moscow (1985), p. 284.
107. K. Imasa, Y. P. Gupta, and M. Cushman, Tetrahedron Lett., 22, 2333 (1981).
108. A. T. Soldatenkov, I. A. Bekro, Zh. A. Mamyrbekova, S. A. Soldatova, A. Temesgen, N. D. Sergeeva, L. N. Kuleshova, and V. N. Khrustalev, Khim. Geterotsikl. Soedin., No. 2, 222 (1996).
109. I. A. Bekro, A. T. Soldatenkov, A. I. Stash, N. Yu. Chernikova, and A. I. Chernishev, Khim. Geterotsikl. Soedin., No. 10, 1372 (1996).
110. K. Morinaga, A. Ueno, S. Fukushima, M. Namikoshi, Y. Iitaka, and S. Okuda, Chem. Pharm. Bull., 26, 2483 (1978).
111. G. L. Kedderis, L. S. Argenbright, and G. T. Miwa, Toxicol. Appl. Pharmacol., 93, 403 (1988);
112. Chem. Abs., 109, 49747 (1988).
113. A. Chatterjee and C. P. Dutta, Tetrahedron, 23, 1769 (1967).
114. B. S. Joshi, V. N. Kamat, and A. K. Saksena, Tetrahedron Lett., No. 20, 2395 (1968).
115. F. R. Filho, M. P. de Souza, and M. E. O. Mattos, Phytochemistry, 20, 345 (1981);
116. Chem. Abs., 96, 20327 (1982).
117. P. M. Boll, J. Hansen, O. Simonsen, and N. Thorup, Tetrahedron, 40, 171 (1985).
118. T. Banerjee and S. Chaudhuri, Can. J. Chem., 64, 876 (1986).
119. Ch. Y. Duh, Y. Ch. Wu, and Sh. K. Wang, J. Nat. Prod., 53, 1575 (1990).
120. Ch. Y. Duh, Y. Ch. Wu, and Sh. K. Wang, Phytochemistry, 29, 2689 (1990);
121. Chem. Abs., 113, 208363 (1990).
122. A. Maxwall and D. Rampersad, J. Nat. Prod., 54, 1150 (1991).
123. R. M. Smith, Tetrahedron, 35, 437 (1979).
124. Y. Gopichand and F. J. Schmitz, J. Org. Chem., 44, 4995 (1979).
125. K. W. Batchelor and S. V. Frye, WO Patent No. 9507927; Izobr. Stran Mira, 041, No. 7, 91 (1996).
126. Ph. L. Durette, W. K. Hagmann, T. J. Lanza, Jr., S. P. Sahoo, G. H. Rasmusson, R. L. Tolman, and L. D. Von, WO Patent No. 9511254; Izobr. Stran Mira, 041, No. 9, 92 (1996).
127. D. W. Graham, S. D. Aster, W. Hagmann, and R. L. Tolman, US Patent No. 5510485; Izobr. Stran Mira, 041, No. 4, 55 (1996).
128. R. T. Coutts and A. F. Casy, Pyridine and its derivatives (Ed. R. A. Abramovitch), Vol. 14, Interscience, New York (1975), p. 445.
129. E. L. Ellsworth, E. Lunney, and B. D. Tait, WO Patent No. 9514012; Chem. Abs., 123, 285777 (1995).
130. B. D. Tait, J. Domagala, E. Ellsworth, D. Ferguson, Ch. Gajda, D. Hupe, E. Lunney, and P. J. Tummino, J. Mol. Recognit., 9, 139 (1996);
131. Chem. Abs., 125, 237611 (1996).
132. A. J. Duplantier, WO Patent No. 9501980; Chem. Abs., 122, 239696 (195).
133. A. J. Duplantier, WO Patent No. 9612720; Chem. Abs., 125, 114610 (1996).
134. J. Nadelson, US Patent No. 4191827; Chem. Abs., 93, 26287 (1980).
135. J. Nadelson, US Patent No. 4131679; Chem. Abs., 90, 186802 (1979).
136. H. Aoki and K. Moryasu, Japanese Patent No. 08325230; Chem. Abs., 126, 104011 (1997).
137. Sh. Nishiyama, T. Inagaki, Sh. Yamamura, H. Koji, M. Junya, and S. Masako, Bull. Chem. Soc. Jpn., 65, 3064 (1992);
138. Chem. Abs., 118, 147383 (1993).