Flavones, isoflavones, and 2- and 3-hetarylchromones in reactions with hydroxylamine. (Review)

Chemistry of Heterocyclic Compounds

Volumn 38, Issue 8, 2002, Pages 883-899

  Khilya, V P ^a   Ishchenko, V V ^a  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

Author keywords

2 hetarylchromones; 3 hetarylchromones; 4 thioxochromenes; Chromone oximes; Flavones; Isoflavones; Isoxazoles

Indexed keywords

4 THIOXOCHROMENE; CHROMONE DERIVATIVE; CHROMONE OXIME; FLAVONE DERIVATIVE; HYDROXYLAMINE; ISOFLAVONE; ISOXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; HYDROGEN BOND; MASS SPECTROMETRY; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0036705917     PISSN: 00093122     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1020920109737     Document Type: Review

References (94)

1. E. Middleton, Jr., Ch. Kandaswami, and Th. C. Theoharides, Pharm. Rev., 52, 673 (2000).
2. A. L. Kazakov, V. P. Khilya, V. V. Mezheritskii, and Yu. Litkei, Natural and Modified Isoflavonoids [in Russian], Izd. Rost. Un-ta., Rostov-on-Don (1985).
3. A. Nohara, H. Kuriki, T. Saijo, H. Sugihara, M. Kanno, and Y. Sanno, J. Med. Chem., 20, 141 (1977).
4. A. Nohara, T. Ishiguro, and Y. Sanno, Ger. Patent 2614836; Chem. Abstr., 86, 72661 (1977).
5. A. Nohara, T. Ishiguro, and Y. Sanno, Ger. Patent 2614836; Chem. Abstr., 86, 72661 (1977).
6. A. Nohara, H. Kuriki, T. Ishiguro, T. Saijo, K. Ukawa, Y. Maki, and Y. Sanno, J. Med Chem, 22, 290 (1979).
7. V. P. Khilya, L. G. Grishko, and D. V. Vikhman, Khim.-Farm. Zh., 10, No. 8, 74 (1976).
8. V. P. Khilya, L. G. Grishko, T. I. Zhirova, N. A. Gorchagova. I. P. Kupchevskaya, and G. M. Golubushina, Khim.-Farm. Zh., 14, No. 1, 24 (1980).
9. V. P. Khilya, A. L. Kazakov, G. M. Golubushina, V. N. Mel'nik, and T. M. Tkachuk, Khim.-Farm. Zh., 15, No. 11, 40 (1981).
10. S. A. Vasil'ev, M. S. Luk'yanchikov, G. I. Molchanov, and V. P. Khilya, Khim.-Farm. Zh., 24, No. 9, 38 (1990).
11. S. A. Vasil'ev, M. S. Luk'yanchikov, G. I. Molchanov, and V. P. Khilya, Khim.-Farm. Zh., 25, No. 7, 34 (1991).
12. E. Petschek and H. Simonis, Berichte, 46, 2014 (1913).
13. H. Simonis and C. B. A. Lehmann, Berichte, 47, 692 (1914).
14. H. Simonis, Ph. Diss., Stuttgart (1917).
15. G. Wittig and F. Bangert, Berichte, 58, 2636 (1925).
16. G. Wittig and F. Bangert, Berichte, 58, 2627 (1925).
17. K. E. Gulati and J. M. Ray, Current Sci., No. 5, 75 (1936).
18. D. G. Flynna and A. Robertson, J. Chem. Soc., 215 (1940).
19. L. Vargha and M. Rados, Acta Chim. Acad. Sci. Hung., 3, 223 (1953).
20. O. Dann, G. Volz, and O. Huber, Liebigs Ann. Chem., 587, 16 (1954).
21. J. Colonge and A. Guyot, Bull. Soc. Chim. France, 325 (1958).
22. S. M. Spatz and M. Koral, J. Org. Chem., 24, 1381 (1959).
23. M. W. Moon and J. C. Sharp, BRD Patent 2513652; Chem. Abstr., 84, 30890 (1976).
24. B. Sen and P. R. Singh., J. Indian Chem. Soc., 37, 217 (1960).
25. R. B. Shenoi, R. S. Shah, and T. S. Wheeler, J. Chem. Soc., 247 (1940).
26. W. Baker, J. B. Harborne, and W. D. Ollis, J. Chem Soc., 1303 (1952).
27. I. Farkas, B. Costisella, M. Rakosi, H. Gross, and R. Bognar, Chem Ber., 102, 1333 (1969).
28. A. Schönberg and M. M. Sidky, J. Am Chem. Soc., 75, 5128 (1953).
29. A. Schönberg, A. K. Fateen, and A. Sammour, J. Am. Chem. Soc., 78, 4689 (1956).
30. A. Sammour, T. Zimaity, and S. Kamel, J. Prakt. Chem., 314, 271 (1972).
31. C. Alberty, Gazz. Chim. Ital., 87, 781 (1957).
32. P. Venturella and A. Bellino, Ann. Chim. (Ital.), 58, 145 (1968).
33. A. Sayed, S. M. Sami, A. Labib, and S. S. Ibrahim, Acta Chim. Acad. Sci. Hung., 87, 165 (1975).
34. P. Crabber, L. A. Moldonado, and J. Sanchez, Tetrahedron, 27, 711 (1971).
35. M. A.-F. Elkaschef, F. M. E. Abdel-Megeid, K.-E. M. Mokhtar, and M. F. Elbamashawi, Indian J. Chem., 11, 860 (1973).
36. W. Basinski and Z. Jerzmanowska, Roczn. Chem., 47, 1785 (1973).
37. W. Basinski and Z. Jerzmanowska, Roczn. Chem., 48, 989 (1974).
38. W. Basinski and Z. Jerzmanowska, Roczn. Chem., 48, 2217 (1974).
39. W. Basinski and Z. Jerzmanowska, Pol. J. Chem., 53, 229 (1979).
40. W. Basinski and Z. Jerzmanowska, Roczn. Chem., 50, 1067 (1976).
41. W. Basinski and Z. Jerzmanowska, in: Flavonoids and Bioflavonoids Current Res Trends, Proceed. 5-th Hung. Bioflavonoid Symp., Natrafured, Hungary (1977), p. 213.
42. M. Królikowska and Z. Witczak, Roczn. Chem., 51, 611 (1977).
43. P. Maib and W. Basinski, Pol. J. Chem., 55, 1527 (1981).
44. R. Beugelmans and Ch. Morin, J. Org Chem., 42, 1356 (1977).
45. Ch. Morin and R. Beugelmans, Tetrahedron, 33, 3183 (1977).
46. R. Beugelmans and Ch. Morin, Tetrahedron Lett., 2145 (1976).
47. Z. Jerzmanowska and W. Basinski, Roczn. Chem., 51, 1791 (1977).
48. J. Schmutz, R. Hirt, and H. Lauener, Helv Chim. Acta, 35, 1168 (1952).
49. U. K. Jagwani, J. Indian Chem. Soc., 49, 293 (1972).
50. S. S. Kumari, K. S. R. K. M. Rao, and N. V. S. Rao, Proc. Indian Acad. Sci., Sect. A, 77, 149 (1973).
51. A. Schönberg, N. Badran, and N. A. Starkowsky, J. Am. Chem. Soc., 75, 4992 (1953).
52. F. Eiden and W. Loewe, Tetrahedron Lett., 1439 (1970).
53. Z. Jerzmanowska, W. Basinski, and L. Zielinska, Pol. J. Chem., 54, 383 (1980).
54. W. Basinski and Z. Jerzmanowska, Pol. J. Chem., 57, 471 (1983).
55. A. Nohara, Tetrahedron Lett., 1187 (1974).
56. F. Eiden, H. Haverland, and W. Loewe, Arch. Pharm. (Weinheim), 306, 929 (1973).
57. U. Petersen and H. Heitzer, Liebigs Ann. Chem., 1659 (1976).
58. Ch. Ghosh, D. K. Sinharov, and K. K. Mukhopadhyay, J. Chem. Soc., Perkin Tram. 1, 1964 (1979).
59. A. T. Prudchenko, L. P. Vovdenko, V. A. Barkhash, and N. N. Vorozhtsov, Jr., Khim. Geterotsikl. Soedin., 967 (1968).
60. N. N. Vorozhtsov, V. A. Barkhash, A. T. Prudchenko, and T. I. Khomenko, Dokl. Akad. Nauk, 164, 1046 (1965).
61. A. R. Katritzky (editor), Advances in Heterocyclic Chemistry, Vol. 2, Academic Press, New York, London (1963), p. 365.
62. L. Claisen, Berichte, 24, 3900 (1891).
63. S. Checchi and V. L. Pecori, Gazz. Chim. Ital., 96, 874 (1966).
64. Z. Jerzmanowska and W. Basinski, Roczn. Chem., 51, 2283 (1977).
65. Y. Kawase and K. Sakashita, Bull. Chem. Soc. Japan, 35, 1869 (1962).
66. V. Szabo, J. Borda, and E. Theisz, Magy. Kem. Folyoirat, 84, No. 3, 134 (1978).
67. V. Szabo, J. Borda, E. Theisz, Acta Chim. Acad. Sci. Hung., 103, 271 (1980).
68. V. Szabo and J. Borda, Topics in Flavonoid Chem. Biochem. Proceed. 4-th Hung. Bioflavonoid Symp. Akad. Kiado, Budapest (1975), p. 52.
69. P. Maib and Jerzmanowska, Pol. J. Chem., 56, 501 (1982).
70. V. Szabo and J. Borda, Magy. Kem. Folyoirat, 82, 36 (1976).
71. V. Szabo, J. Borda, and L. Losonczi, Magy. Kem. Folyoirat, 83, 278 (1977).
72. V. Szabo, L. Nemeth, J. Borda, and G. Bokor, Magy. Kem. Folyoirat, 85, 385 (1979).
73. V. Szabo, J. Borda, and Vegh, Magy. Kem. Folyoirat, 83, 433 (1977).
74. L. G. Grishko, I. P. Kupchevskaya, and V. P. Khilya, Dokl. Akad. Nauk UkrSSR. Ser. B, 518 (1978).
75. V. P. Khilya, L. G. Grishko, G. M. Golubushina, and N. V. Gorbulenko, Ukr. Khim. Zh., 56, 280 (1990).
76. V. P. Khilya, K. Uteniyazov, K. Ismailova, and A. Aitmanbetov, Vestn. KKAFAN UzSSR, No. 1, 14 (1986).
77. I. P. Kupchevskaya and V. P. Khilya, Dokl. Akad. Nauk UkrSSR. Ser. B, 236 (1978).
78. V. P. Khilya, M. Yu. Komilov, I. P. Kupchevskaya, and V. F. Vakulenko, Ukr. Khim. Zh., 44, 265 (1978).
79. V. P. Khilya, T. M. Tkachuk. I. P. Kupchevskaya, and G. M. Golubushina, Dokl. Akad. Nauk UkrSSR Ser. B, 61 (1980).
80. L. G. Grishko, V. P. Khilya, M. F. Sedyuko, and D. Litkei, Ukr. Khim. Zh., 51, 211 (1985).
81. I. P. Kupchevskaya and V. P. Khilya, Dokl. Akad. Nauk UkrSSR Ser. B, 119 (1979).
82. V. P. Khilya, I. P. Kupchevskaya, A. L. Kazakov, T. M. Tkachuk, and G. M. Golubushina, Khim. Geterotsikl. Soedin., 321 (1982).
83. V. P. Khilya, L. G. Grishko, and T. L. Davydkova, Khim. Geterotsikl. Soedin., 892 (1980).
84. V. P. Khilya, N. V. Gorbulenko, and V. V. Trachevskii, Dokl. Akad. Nauk UkrSSR. Ser. B, 117 (1991).
85. N. V. Gorbulenko, N. N. Shimko, and V. P. Khilya, Dokl. Akad. Nauk UkrSSR. Ser. B, 117 (1991).
86. N. V. Gorbulenko, M. S. Frasinyuk, and V. P. Khilya, Khim. Geterotsikl. Soedin., 464 (1994).
87. N. V. Gorbulenko, S. A. Kirpa, and V. P. Khilya, Khim. Geterotsikl. Soedin., 29 (1993).
88. M. S. Frasinyuk and V. P. Khilya, Khim. Geterotsikl. Soedin., 3 (1999).
89. V. P. Khilya and N. V. Gorbulenko, Ukr. Khim. Zh., 60, 79 (1994).
90. V. Szabo, J. Borda, L. Losonczi, Acta Chim. Acad. Sci. Hung., 97, 69 (1978).
91. V. Szabo and J. Borda, Acta Chim. Acad. Sci. Hung., 95, 333 (1977).
92. J. B. Harbome and T. J. Mahry (editors), The Flavonoids: Advances in Research, Chapman and Hall, London, New York, (1982), p. 744.
93. K. Breitmaier and W. Voelter, 13C NMR Spectroscopy: Methods and Applications, 2nd edition, Verlag Chemie, Weinheim, New York (1978).
94. B. V. Ioffe, I. G. Zenkevich, M. A. Kuznetsov, and I. Ya. Bershtein, New Physical Methods of Investigation of Organic Compounds [in Russian], Izd. Leningrad Univ. (1984).