The utility of nitroacetic acid and its derivatives in the synthesis of heterocycles

Current Organic Chemistry

Volumn 5, Issue 5, 2001, Pages 553-570

  Kislyi, V V ^a   Samet, A V ^a   Semenov, V V ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; NITRATION;

AMINO GROUP; BIOLOGICALLY ACTIVE COMPOUNDS; HETEROCYCLES; LOW-YIELD; METRONIDAZOLE; MIXTURES OF ISOMERS; NITRATING REAGENTS; NITRO GROUP; NITROACETIC ACID; POTENTIAL HAZARDS;

ISOMERS;

ACETIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; METRONIDAZOLE; NITRAZEPAM; NITROXOLINE; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE; THIOPHENE DERIVATIVE;

CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; ISOMER; NITRATION; REVIEW; STRUCTURE ANALYSIS;

EID: 0034999630     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272013375445     Document Type: Review

References (134)

1. Rajappa, S., Nair, M. D. Adv. in Het. Chem., 1979, 25, 113..
2. Shipchandler, M. T. Synthesis, 1979, 666.
3. Zlotin, S. G., Varnaeva, G. N., Lukjanov, O. A. Usp. Khimii (Russ.)., 1989, 796.
4. Rajappa, S. Tetr., 1981 , 37, 1453.
5. Tominaga, Y., Matsuda, Y. J. Het. Chem., 1985, 22, 937.
6. Pillai, P., Boyer, J. H. Org. Prep. Proced. Int., 1982, 14, 365.
7. Munz, R., Simchen, G. Lieb. Ann., 1979 , 628 .
8. Ried, W., Kohler, E. Lieb. Ann., 1956 , 598, 145.
9. Mattews, V. E., Kubler, D. G. J. Org. Chem., 1960, 25, 266.
10. Zen, S., Koyama, M., Koto, S. Org. Synth,. 1976, 55, 77.
11. Finkbeiner, H. L., Stiles, M. J. ACS, 1963, 85, 616.
12. Sifniades, S. J. Org. Chem., 1975, 40, 3562 .
13. Kisliy, V. P., Laikhter, A. L., Ugrak, B. I., Semenov, V. V. Izv. Akad. Nauk SSSR, Ser. Khim., 1994, 76.
14. Adolph, H. G., Kamlet, M. J. J. Am. Chem. Soc., 1966,88, 4761.
15. Baer, H. H., Urbas, L., in The Chemistry of the nitro and nitrozo groups, H. Feuer, Ed., Part 2, Interscience, N. Y. 1970, p. 75.
16. Umezawa, S., Zen, S. Bull Chem. Soc. Jpn, 1963, 36, 1143.
17. Dornow, A., Frese, A. Lieb. Ann. Chem., 1953, 581, 211.
18. Dornow, A., Wiehler, G. Lieb. Ann., 1952, 578, 113.
19. Dornov, A., Frese, A. Lieb. Ann. Chem., 1952, 578, 122.
20. Vinograd, L. Kh., Suvorov, N. N. Khim. Geterotsikl. Soedin, 1970, 1505,-CA v. 74, 53610(1971).
21. Aboskalova, N. I., Poljanskaja, A. S., Perekalin, V. V. Zh. Org. Khim., 1972, 8, 1332.
22. Lehnert, W. Tetrahedron, 1963, 28, 663.
23. Dornow, A., Menzel, H. Lieb. Ann. Chem,. 1954, 588, 40.
24. Wolfbeis, O. S. Chem. Ber,. 1981, 114, 3471.
25. Gomes-Sanchez, A., Hidolgo-Garcia, F., Chiara, J. L., Bellanato, J. An. Quim., Ser. C., 1985, 81, 139.
26. Grivas, J. C., Taurins, A. Can. J. Chem., 1959, 37, 1266.
27. Brownstein, S. K., J. Org. Chem., 1958, 23, 113 .
28. Kislyi, V. P., Shestopalov, A. M., Kagramanov, N. D., Semenov, V. V. Izv. Akad. Nauk SSSR, Ser. Khim., 1997, 559.
29. Ungnade, H. E., Kissinger, L. W. J. Org. Chem,. 1957, 22, 1662.
30. Freund, E. Ber. Dtsch. Chem. Ges., 1919, 52, 542 .
31. Gompper, R., Schaefer, H. Chem. Ber., 1967, 100, 591 .
32. Kearmy, T., Harris, P., Jackson, A., Joule, J. A. Synth., 1992, 769 .
33. Manjunatha, S. G., Reddi, K. V., Rajappa, S. Tetrahedron Lett., 1990, 31, 1327 .
34. Mertens, H., Troschuetz, R., Roth, H. J. Arch. Pharm., 1986, 319, 14.
35. Schafer, H., Bartho, B., Gewald, k. J. Prakt. Chem., 1977, 319, 149.
36. th, 1978, v. 2, p. 216-7; CA91:103657.
37. Koichi, K., Shibuya, K. et al., J. Pestic Sci. (Int. Ed.), 1993, 18, 119; -23; CA 119:22788.
38. Iminamida, Iwanaga , K. et al., J. Pestic Sci. (Int. Ed.), 1993, 18, 31.
39. Iminamida, Iwanaga , K. et al., J. Pestic. Sci. (Int. Ed.), 1993, 18, 41.
40. Haywood, Ph., Martin-Smith, M. et al., J. Chem. Soc., Perkin, 1987, 1, 951.
41. Young, R., Mitchell, R., et al., J. Med. Chem., 1988, 31, 656.
42. Rajappa, S., Sreenivasan, R., Advani, B. G., Summerville, R. H., Hoffman, R. Indian J. Chem., 1977, 15B, 297 .
43. Reddy, T. I., Bhawal, B. M., Rajappa, S. Tetrahedron, 1993, 49, 2101.
44. Ried, W., Sinharay, A. Chem Ber., 1963, 96, 3306.
45. Ried, W., Stoch, P. Lieb. Ann., 1966, 700, 87.
46. Harris, P. A., Jackson, A., Joule, J. A. Tetrahedron Lett., 1989, 30, 3193.
47. Harris, P. A., Jackson, A., Jackson, Joule, J. A. Tetrahedron Lett., 1989, 30, 3189.
48. Mukaiyama, T., Hosino, T. J. Am. Chem. Soc., 1960, 82, 5339.
49. Michael, A. Chem. Ber., 1905, 38, 39 .
50. Steinkopf, W., Daege, H. M. Chem. Ber., 1911, 44, 497 .
51. [51 ] Paul, R., Tchelitcheff, S. Bull. Chem. Soc. Fr., 1963, 140.
52. Huisgen, R., Christi, M. Chem. Ber., 1973, 106, 3291.
53. Boyel, R. N., Leshin, R. J. Am. Chem. Soc., 1953, 75, 2762.
54. Zen, S., Kaji, E., Takahashi, K. Nippon Kagahy Kaishy., 1986, 55.
55. Melot, J. -M., Texier-Boullett, F., Foucaud, A. Synthesis, 1988, 558.
56. Harada, K., Kaji, E., Sasak, K., Zen, Sh. Heterocycles, 1996, 42, 289.
57. Rosini, G., Galarini,. R., Maratta, E. J. Org. Chem., 1990, 55,781 .
58. C. Galli, E. Marotta, P. Righi, G. Rosini. J. Org. Chem., 1995, 60, 6624.
59. Rosini, G., Marotta, E., Righi, P., Seerden, J., Org, J. Chem., 1991, 56, 6258.
60. Metelkina, E. L., Sopova, A. S., Perekalin, V. V., Ionin, V. I. Zh. Org. Khim., 1974, 10, 209.
61. Kaji, E., Harada, K., Zen, S. Chem. Pharm. Bull., 1978, 26, 3254.
62. Shimizu, T., Huyashi, Y., Teramura, K. Bull. Jpn., 1984, 57,2531 .
63. Shimizu, T., Hirohi, H., Teramura, K. Bull. Jpn., 1986, 59, 2827 .
64. Sugiama, T., Ohno, A., Oka, Sh., Susumi, H. Kidorui, 1989, 12, 112; CA 109:230867m.
65. Shimizu, T., Huyashi, Y., Hirohi, H., Teramura, K. J. Org. Chem., 1983, 48, 3053.
66. Barlas, J., Grook, S., Leslie, M. G., Paton, R. M., Webb, W. Chem. Ind. (London), 1986,16, 534 .
67. Kisliy, V. P., Iaikhter, A. L., Ugrak, B. I., Semenov, V. V. Izv. Akad. Nauk SSSR, Ser. Khim., 1994, 103.
68. Shimuzu, T., Hayashi, Y., Ito, T., Teramura, K. Synthesis, 1986, 488.
69. Kashutina, M. V. et al., Zh. Obshch. Khim., 1973, 43, 1715.
70. Krasnaya , Zh. A. et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1974, 845; CA 81:49608(1974).
71. Marotta, E., Righi, P., Rosini, G. Tetrahedron Lett., 1998, 39, 1041.
72. Haves, E. M., Wibberley, D. G. J. C. S., ser. C, 1966, 315.
73. Yang, J., Lambert, C., Langmuir, M., Org. Prep. Proceed. Int., 1991, 23, 621.
74. Dauzonne, D., Royer, Eur, R.,. J. Med. Chem. Chem. Ther., 1984, 19, 477.
75. Gorin, B. I. et al., Khim. Geterotsikl. Soedin., 1985, 82; CA 102:220815.
76. Hadtmann, G. E. Ger. Offen., 1977, 2, 635, 216; - CA 87:23245 .
77. Copolla, G. M., Fraser, J. D., Hardtmann, G. E., Shapiro, M. J. Heterocycl. Chem., 1985, 22, 193.
78. Copolla, G. M., Hardtmann, G. E., Pfizer, O. R. J. Org. Chem., 1976, 41, 825.
79. Kuroda, T., Suzuki, F. J. Het. Chem., 1976, 28, 2029(1991).
80. Vincentini, Veronese, C., A., Guarneri, M., Giori, P., Heterocycles, 1991, 32, 79.
81. Dornow, A., Rohe, E. -H. Chem. Ber., 1960, 93, 1093.
82. Maguire, J. H., McKee, R. L., J. Heter. Chem., 1979, 16, 133.
83. Moline, P. S., Span. EP 512, 599 - CA 100:P174671 .
84. Hoffman, J. M., Wai, J. S., Thomas, C. M., Levin, R. B., O'Brien, J. A., Goldman, M. E. J. Med. Chem., 1992, 35, 3784.
85. Saari, W. S., Wai, J. S., Fisher, T. E., Thomas, C. M., Hoffman, J. M., Rooney, C., Smith, A. M., Jones, J. H., Bamberger, D. L., M. E., O'Brien, J. A., Nunberg, J. H., Quintero, J. C., Schleif, W. A., Emini, E. A., Anderson, P. S. J. Med. Chem., 1992, 35, 3792.
86. Wai, J. S., Williams, T., Bamberger, D. L., Fisher, T. E., Hoffman, J. M., Hudkosky, R. J., MacTough, S. C., Rooney, C. S., Saari, W. S., Thomas, C. M., Goldman, M. E., O'Brien, J. A., Emini, E. A., Nunberg, J. H., Quintero, J. C., Schleif, W. A., Anderson, P. S. J. Med. Chem., 1993, 36, 249.
87. Hoffman, J. M., Smith, A. M., Rooney, C. S., Fisher, T. E., Wai, J. S., Thomas , C. M., Bamberger, D. L., Barnes, J. L., Wiliams, T. M., Jones, J. H., Olson, B. D., O'Brien, J. A., Goldman, M. E., Nunberg, J. H., Quintero, J. C., Schleif, W. A., Emini, E. A., Anderson, P. S. J. Med. Chem., 1993, 36,953 .
88. Wallace, M., Dean, D. C., Ellsworth, R. L., Melillo, D. G. J. LabelledCompd. Radiopharm, 1996, 38, 155.
89. Eur. Pat. Appl. EP 509, 769; - CA 119:8683(1993).
90. PCT Int. Appl., WO 97 01, 336 CA 128: 308732(1998).
91. Samet, A. V., Kislyi, V. P., Chernyshova, N. B., Ugrak, B. I., Semenov, V. V. Izv. Akad. Nauk SSSR, Ser. Khim., p. 40P; - CA125:195531d.
92. Samet, A. V., Niyazymbetov, M. E., Semenov, V. V., Laikhter, A. L., Evans, D. H. J. Org. Chem., 1996, 61, 8786; ; CA 126: 47422j.
93. Prystas, M., Gut, J. Coll. Czech. Chem. Comm., 1977, 7, 269.
94. Wolfbeis, O. S. Synth., 1977, 136 .
95. De la Cuesta, E., Avendano, C. J. Het. Chem., 1985, 22, 337.
96. Yamazaki, Ch., Takahashi, T. Hata, K. Perkin, 1988, 1, 1897.
97. Woifbeis, O. S. Chem. Ber., 1977, 110, 2480.
98. Thyagarajan, B. S., Gopalakrishnan, P. V. Tetrahedron, 1964, 20, 1051.
99. Patrick, J., Rami, H. J. Chem. Res. Synop., 1990,308.
100. Brimble, M., Johnston, A. D. Tetrahedron, 1994, 50, 4887.
101. Hugener, M., Heimgartner, H. Helv. Chim. Acta, 1995, 78, 1490.
102. Kuzmenko , T. A. et al, Khim. Geterotsikl. Soedin., 1992, 205.
103. Bruche, L., garanti, L, Zecchi, G. Gazz. Chim. Ital, 1981, 111, 337.
104. Aydin, A., Fewer, H. Acta Turc., 1979, 7, 121.
105. Aydin, A, Fewer, H. Acta Turc., 1981, 9, 199.
106. Barco, A. et al., J. Med. Chem., 1981, 24, 625.
107. Piaz, V. D., Pinzantis, S., Lacrimini, P. Synth., 1975, 664.
108. Jpn Kokai JP 81, 100, 780; -CA 96:p19954t.
109. Kipriyanov, A. N., Verbovskaya, T. M. Zh. Obshchei Khim., 1962, 32, 3703; CA 58:11349(1962).
110. Schaefer, H., Gewald, K. Z. Chem., 1976, 16, 2721.
111. Kanishchev, M. I., Korneeva, Korneeva, N. V., Shevelev, S. A. Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 2342.
112. Rajappa, S. Indian J. Chem., 1977, 15, 890.
113. Kislyi, V. P., Nesterov, V. N., Shestopalov, A. M., Semenov, V. V. Izv. Akad. Nauk SSSR, Ser. Khim., 1998, 1142.
114. Kislyi, V. P., Nesterov, V. N., Shestopalov, A. M., Semenov, V. V. Izv. Akad. Nauk SSSR, Ser. Khim., 1998, 1146.
115. Rysinov, V. L., Dragunova, T. V., Chupahin, Chupahin, O. N. Khim. Geterotsikl. Soedin, 1984, 557; -CA 101: 90884.
116. Rysinov, V. L., Petrov, Ju. A., Chupahin, O. N., Kluev, N. A. Khim. Geterotsikl. Soedin, 1985, 682; -CA 104: 50851.
117. Gundermann, K. D., Alles, H. U. Angew. Chem. Int., 1966, 5, 848.
118. Tominaga, Y., Shiroshita, Y., Hosomi, A. J. Het. Chem., 1988, 25, 1745.
119. Gupta, A., Chakrasali, R., Ila, H., Junjappa, H. Synth., 1989, 141.
120. Thomas, A., Rajappa, S. Tetrahedron, 1995, 51, 10571.
121. Troschuetz R., Lueckel A. Arch. Pharm., 1989, 322, 664 .
122. Urbahns , K.et al., Ger Offen DE 4, 430, 638; CA 124:P343121s.
123. Troschuetz R., Lueckel A. Arch. Pharm., 1991, 342, 73.
124. Mertens H., Troschuetz R. Arch. Pharm., 1986, 319, 947.
125. Schafer, H., Gewald, K. Z. Chem., 1978, 18, 335.
126. Mertens H., Troschuetz R. Arch. Pharm., 1987, 320, 1143.
127. Stuck, G., Roduit, J., Schmidt, B. Chimia, 1997, 51, 280.
128. Batt, D., Houghton, G. J. Het. Chem., 1995, 32, 963.
129. Kuo, D. et al., Eur. Pat. Appl. EP 656, 358; - CA 123:P286019t.
130. Hirata, K., Kaai, H. Jpn. Kokai, 08, 245, 591; - CA 125:P328522a.
131. Tokumitsu, T. Bull. Chem. Soc. Jpn, 1990, 63, 1921.
132. Zhi-tang H., Lu-hang T. Chem. Ber., 1986119, 2208.
133. Takahashi, M., Nozaki, Ch., Shibazaki, Y. Chem. Lett., 1987, 1229.
134. Schafer, H., Gewald, K. J. Prakt. Chem., 1980, 322, 87.