Skip to main content
SpringerLink
Log in

Properties and application of aryl-substituted azines (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Aryl-substituted six-membered azaaromatic heterocycles have a range of properties that make it possible to use them in scientific investigations and in modern regions of technology. The possibilities of using arylazines in chemical analysis, in catalytic processes, and as optical and photochromic materials in polymer chemistry are surveyed.

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

Similar content being viewed by others

References

  1. T. Shibamoto, Koryo,111, 69 (1975); Chem. Abstr.,84, 149375 (1976).

    Google Scholar 

  2. O. G. Vitzthum, P. Werkhoff, and P. Hubert, J. Food Sci.,40, 911 (1975); Chem. Abstr.,83, 130246 (1975).

    Google Scholar 

  3. M. Duenger, S. African Patent No. 6,906,582; Chem. Abstr.,73, 106474 (1970).

    Google Scholar 

  4. A. F. Thomas and F. Bassols, J. Agric. Food Chem.,40, 2236 (1992); Chem. Abstr.,117, 211047 (1992).

    Google Scholar 

  5. M. Ishihara, T. Tsuneya, M. Shiga, S. Kawashima, K. Yamagishi, F. Yoshida, H. Sato, and K. Uneyama, J. Agric. Food Chem.,40, 1647 (1992); Chem. Abstr.,117, 137400 (1992).

    Google Scholar 

  6. X. A. Dominguez, G. Fuente, A. G. Gonzalez, M. Reina, and I. Timon, Heterocycles,27, 35 (1988).

    Google Scholar 

  7. J. J. Brophy and G. W. K. Cavill, Heterocycles,14, 477 (1980).

    Google Scholar 

  8. G. Ohloff and I. Flament,11, 663 (1978).

  9. O. Nishimura, H. Masuda, and S. Mihara, Koryo,165, 91 (1990); Chem. Abstr.,113, 210350 (1990).

    Google Scholar 

  10. W. M. Coleman, J. Chromatogr. Sci.,30, 159 (1992).

    Google Scholar 

  11. S. Matsushima, T. Ohsumi, and S. Sugawara, Agric. Biol. Chem.,47, 507 (1983); Chem. Abstr.,98, 195196 (1983).

    Google Scholar 

  12. E. Leete, Biogenesis of Natural Compounds, P. Bernfeld (ed.), Pergamon, Oxford (1963), Chapt. 17.

  13. W. R. Kem, R. N. Scott, and J. H. Duncan, Experientia,32, 684 (1976); Chem. Abstr.,85, 59926 (1976).

    Google Scholar 

  14. M. P. Cruskie, J. A. Zoltewicz, and K. A. Abboud, J. Org. Chem.,60, 7491 (1995).

    Google Scholar 

  15. B. D. Alreja, S. L. Kattige, B. Lal, and N. J. de Souza, Heterocycles,24, 1637 (1986).

    Google Scholar 

  16. M. Aoki, T. Ohtsuka, Y. Itezono, K. Yokose, K. Furihata, and H. Seto, Tetrahedron Lett.,32, 221 (1991).

    Google Scholar 

  17. L. N. Tokareva, G. D. Gal'pern, A. V. Kotova, and I. D. Leonov, Neftekhimiya,7, 790 (1967).

    Google Scholar 

  18. L. A. Summers, Adv. Heterocycl. Chem.,35, 281 (1984).

    Google Scholar 

  19. Y. Sakon, T. Ohnuma, M. Hashimoto, T. Saito, T. Tsutsui, and C. Adachi, US Patent No. 5,077,142; Chem. Abstr.,117, 16862 (1992).

    Google Scholar 

  20. S. Bohm, A. Stadlik, J. Kuthan, and O. Richter, Czech. Patent No. 255,764; Chem. Abstr.,111, 194603 (1989).

    Google Scholar 

  21. A. Kurfuerst, P. Lhotak, J. Kuthan, and O. Richter, Czech. Patent No. 256,977; Chem. Abstr.,111, 115053 (1989).

    Google Scholar 

  22. A. Krufürst, P. Lhotak, M. Petru, and J. Kuthan, Coll. Czech. Chem. Commun.,54, 462 (1989).

    Google Scholar 

  23. R. Pater, J. Heterocyclic Chem.,7, 1113 (1970).

    Google Scholar 

  24. CIBA Ltd., French Patent No. 1,396,684; Chem. Abstr.,63, 9964 (1965).

    Google Scholar 

  25. L. Maskiya, Additives for Plastics [Russian translation], Khimiya, Moscow (1978), p. 144.

    Google Scholar 

  26. G. Reinert and K. Burdeska, Eur. Pat. Appl. 280,654; Chem. Abstr.,110, 77445 (1989).

    Google Scholar 

  27. J. E. A. Otterstedt and R. Pater, J. Heterocyclic Chem.,9, 225 (1972).

    Google Scholar 

  28. J. E. A. Otterstedt and R. Pater, US Patent No. 3,787,428; Ref. Zh. Khim., 4N261P (1975).

  29. B. Helmo, H. P. Jakob, and H. Heller, US Patent No. 3,896,125; Chem. Abstr.,84, 5828 (1976).

    Google Scholar 

  30. M. Slongo, J. L. Birbaum, J. Rody, and A. Valet, Eur. Pat. Appl. 453,405; Chem. Abstr.,116, 41487 (1992).

    Google Scholar 

  31. M. Sudo, T. Muraki, E. Kawaki, E. Kawachi, and Y. Kawachi, Jpn. Pat. Appl. 03,190,864; Chem. Abstr.,115, 280067 (1991).

    Google Scholar 

  32. A. Grobowska and L. Kaczmarek, Pol. J. Chem.,66, 715 (1992); Chem. Abstr.,117, 211699 (1992).

    Google Scholar 

  33. H. Brunetti, German Patent No. 2,155,453; Chem. Abstr.,77, 62782 (1972).

    Google Scholar 

  34. T. Ozeki, T. Yagi, H. Haruna, and H. Takahashi, Jpn. Pat Appl. 61,179,245; Chem. Abstr.,106, 34036 (1987).

    Google Scholar 

  35. V. I. Kelarev, R. A. Karakhanov, V. R. Mkrtchan, and A. S. Kokosova, Khim. Tekhnol. Topliv. i Masel, No. 5, 32 (1990); Chem. Abstr.,113, 100538 (1990).

    Google Scholar 

  36. T. S. Tran, M. D. Vu, and H. Thai, Tap Chi Hoa Hoc,24, 22 (1986); Chem. Abstr.,106, 177380 (1987).

    Google Scholar 

  37. M. Horio and T. Misumi, Jpn. Pat. Appl. 02,300,259; Chem. Abstr.,114, 230115 (1991).

    Google Scholar 

  38. M. Yanagawa, US Patent No. 4,501,689; Chem. Abstr.,102, 222327 (1985).

    Google Scholar 

  39. Yokohama Rubber Co., Jpn. Pat Appl. 59,159,872; Chem. Abstr.,102, 133162 (1985).

    Google Scholar 

  40. E. Takahashi, T. Morikawa, and H. Haruta, Jpn. Pat. Appl. 03,256,048; Chem. Abstr.,116, 162556 (1992).

    Google Scholar 

  41. K. Ogi, T. Yoshizawa, and H. Sakamoto, Jpn. Pat. Appl. 01,229,241; Chem. Abstr.,112, 169016 (1990).

    Google Scholar 

  42. T. Kamamura, S. Goto, and Y. Suda,111, 105859 (1989).

  43. A. Ezaki, H. Akamatsu, and N. Kagawa, Jpn. Pat. Appl. 62,196,648; Chem. Abstr.,108, 121982 (1988).

    Google Scholar 

  44. H. Sakamoto, Y. Kaneko, and H. Ninomiya, Jpn. Pat. Appl. 62,187,837; Chem. Abstr., 29973 (1988).

  45. H. Sakamoto, Y. Kaneko, and H. Ninomiya, Jpn. Pat. Appl. 62,156,654; Chem. Abstr.,107, 225938 (1987).

    Google Scholar 

  46. A. S. Trofimov, V. I. Eroshkin, V. P. Krivopalov, T. A. Andreeva, and V. P. Mamaev, Inventor's Certificate No. 1,173,375; Byull. Izobret., No. 30, 193 (1985).

    Google Scholar 

  47. T. A. Andreeva, V. I. Eroshkin, V. P. Krivopalov, V. P. Mamaev, and A. S. Trofimov, Avtometriya, No. 4, 3 (1991).

    Google Scholar 

  48. T. A. Andreeva, V. I. Eroshkin, V. P. Krivopalov, E. B. Nikolaenkova, and V. P. Mamaev, Inventor's Certificate No. 1,819,004; Byull. Izobret., No. 10, 252 (1995).

    Google Scholar 

  49. M. I. Dobrikov, E. L. Mishchenko, and G. V. Shiskin, Izv. Sibirsk. Otd. Akad. Nauk SSSR. Ser. Khim., No. 3, 133 (1989).

    Google Scholar 

  50. S. Truchlik, V. Kabatova, M. Dimun, and S. Zerman, Thermochim. Acta,92, 205 (1985); Chem. Abstr.,105, 42130 (1986).

    Google Scholar 

  51. NASA Contact Rep. 1975; Sci. Tech. Aerosp. Rep.,14, No. 76-22397; Chem. Abstr.,85, 145386 (1976).

  52. Ricoh Co., Jpn. Pat. Appl. 59,177,566; Chem. Abstr.,102, 87608 (1985).

    Google Scholar 

  53. V. M. Ostrovskaya, O. T. Lushina, L. V. Lomakina, M. S. Aksenova, I. A. Krasavin, V. A. Inshakova, E. K. Mamaeva, V. P. Mamaev, V. P. Krivopalov, and O. A. Zagulyaeva, German Patent No. 3,902,453; Chem. Abstr.,114, 258778 (1991).

    Google Scholar 

  54. V. M. Ostrovskaya, L. V. Lomakova, N. A. Fomin, M. S. Aksenova, O. N. Garicheva, A. V. Ivashchenko, V. P. Mamaev, V. P. Krivopalova, and I. G. Gakh, Inventor's Certificate No. 1,178,819; Byull. Izobret., No. 34, 94 (1985).

    Google Scholar 

  55. V. M. Ostrovskaya, L. V. Lomakina, N. A. Fomin, M. S. Aksenova, O. N. Garicheva, A. V. Ivashchenko, V. P. Mamaev, V. P. Krivopalov, and I. G. Gakh, German Patent No. 3,309,000; Chem. Abstr.,102, 89346 (1985).

    Google Scholar 

  56. A. V. Ivashchenko, Dichroic Dyes for Liquid Crystal Displays, CRC Press, London (1994), p. 190.

    Google Scholar 

  57. G. Pelzl, H. Zaschke, and D. Demus, Displays,6, No. 3, 141 (1985); Chem. Abstr.,104, 12916 (1986).

    Google Scholar 

  58. D. Demus, H. Zaschke, G. Pelzl, H. Enzenberg, and A. Isenberg, German Patent No. 3,408,042; Chem. Abstr.,102, 158242 (1985).

    Google Scholar 

  59. H. Zaschke, H. Schubert, F. Kuschel, F. Dinger, and D. Demus, DDR Patent No. 95,892; Chem. Abstr.,80, 32446 (1974).

    Google Scholar 

  60. G. Kraus and A. Kolbe, J. Chromatogr.,147, 17 (1978); Chem. Abstr.,88, 79522 (1978).

    Google Scholar 

  61. L. Sojak, G. Kraus, I. Ostrovsky, E. Kralovicova, and J. Krupcik, J. Chromatogr.,206, 475 (1981); Chem. Abstr.,94, 219065 (1981).

    Google Scholar 

  62. K. Isomura, Y. Oozono, K. Takehara, M. Era, T. Tsutsui, and S. Saito, Thin Solid Films,178, 351 (1989).

    Google Scholar 

  63. Y. Shudo, K. Ujiie, M. Sasaki, and M. Hashimoto, Jpn. Pat. Appl. 01,185,527; Chem. Abstr.,112, 87907 (1990).

    Google Scholar 

  64. D. Dorsch, R. Eidenschink, B. Rieger, and G. Marowsky, German Patent Appl. 3,641,024; Chem. Abstr.,110, 15768 (1989).

    Google Scholar 

  65. C. C. Frazier, M. P. Cockerham, E. A. Chauchard, and C. H. Lee, J. Opt. Soc. Am., B, Opt. Phys.,4, 1899 (1987); Chem. Abstr.,108, 46448 (1988).

    Google Scholar 

  66. L. A. Lee, US Patent No. 4,506,368; Chem. Abstr.,102, 229283 (1985).

    Google Scholar 

  67. M. Matsuo, T. Sakaguchi, Y. Muroyama, and N. Akamatsu, Jpn. Pat. No. 7,414,849; Chem. Abstr.,82, 45070 (1975).

    Google Scholar 

  68. H. M. Muramatsu, K. Shibata, and M. Matsui, Jpn. Pat. Appl. 04,279,568; Chem. Abstr.,118, 61532 (1993).

    Google Scholar 

  69. D. R. Waring, Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees (eds.), Vol. 1, Part 1, Pergamon, Oxford (1984), p. 339.

    Google Scholar 

  70. H. Zollinger, Color Chemistry, VCH, Weinheim (1987), pp. 191, 207.

    Google Scholar 

  71. J. R. Allan, B. R. Carson, D. L. Gerrard, and J. Birnie, Eur. Polymer J.,26, 241 (1990); Chem. Abstr.,112, 236361 (1990).

    Google Scholar 

  72. A. T. Pilipenko and E. R. Falendysh, Usp. Khim.,41, 2094 (1972).

    Google Scholar 

  73. W. A. Butte and F. H. Case, J. Org. Chem.,26, 4690 (1961).

    Google Scholar 

  74. J. J. Lafferty and F. H. Case, J. Org. Chem.,32, 1591 (1967).

    Google Scholar 

  75. A. A. Schult, J. F. Wu, and F. H. Case, Talanta,23, 543 (1976).

    Google Scholar 

  76. R. Belcher, M. Y. Kuchawar, and W. I. Stephen, J. Chem. Soc. Pak.,11, 185 (1989); Chem. Abstr.,113, 40625 (1990).

    Google Scholar 

  77. M. Y. Kuchawar and Z. P. Memon, J. Chem. Soc. Pak.,5, 55 (1983); Chem. Abstr.,99, 224246 (1983).

    Google Scholar 

  78. B. M. Kelly-Basetti, D. J. Cundy, S. M. Pereira, W. H. F. Sasse, G. P. Savage, and G. W. Simpson, Bioorg. Med. Chem. Lett.,5, 2989 (1995).

    Google Scholar 

  79. E. Solem, U. B. Seiffert, U. B. Jalner, M. Kaul, L. J. Behnken, K. Froehlich, and M. Zirker, J. Clin. Chem. Clin. Biochem.,26, 697 (1988); Chem. Abstr.,110, 53997 (1989).

    Google Scholar 

  80. B. G. Stephens and H. A. Suddeth, Analyst,95, No. 1126, 70 (1970); Chem. Abstr.,72, 96408 (1970).

    Google Scholar 

  81. E. Yoneda, M. Takehisa, K. Kochi, and H. Yashima, Hiroshima-Kenritsu Byoin Nempo,10, 97 (1978); Chem. Abstr.,90, 134683 (1979).

    Google Scholar 

  82. T. W. Stephens, PCT Int. Patent Appl. 8,302,670; Chem. Abstr.,99, 209285 (1983).

    Google Scholar 

  83. B. R. Day, D. R. Williams, and C. A. Marsh, Clin. Biochem.,12, 22 (1979); Chem. Abstr.,90, 147988 (1979).

    Google Scholar 

  84. M. Unoki, M. Fujiwara, T. Aoyama, A. Kaku, and S. Shin, Jpn. Pat. Appl. 79,134,694; Chem. Abstr.,92, 72293 (1980).

    Google Scholar 

  85. Wako Pure Chem. Ind. Ltd., Jpn. Pat. Appl. 5,932,867; Chem. Abstr.,100, 171198 (1984).

    Google Scholar 

  86. D. G. Sankar, C. S. P. Sastry, M. N. Reddy, and M. Aruna, Indian J. Pharm. Sci.,50, 178 (1988); Chem. Abstr.,109, 237154 (1988).

    Google Scholar 

  87. S. Tsurubou and T. Sakai, Gifu Shika Daigaku Shingakubu Kenkyu Hokoku,9, 91 (1983); Chem. Abstr.,100, 131635 (1984).

    Google Scholar 

  88. M. C. Mehra, M. Satake, L. F. Chang, and H. B. Singh, Microchem. J.,31, 392 (1985); Chem. Abstr.,103, 115224 (1985).

    Google Scholar 

  89. T. Nagahiro, M. Satake, and B. K. Puri, Zh. Anal. Khim.,40, 1601 (1985).

    Google Scholar 

  90. Y. Sasaki, Anal. Chem. Acta,98, 335 (1978); Chem. Abstr.,89, 70395 (1978).

    Google Scholar 

  91. C. Musikas, P. Vitorge, R. Fitoussi, M. Bonnin, and D. Pateevialard-Goudou, Radioact. Waste Manage.,6, 255 (1982); Chem. Abstr.,98, 61821 (1983).

    Google Scholar 

  92. M. Bonnin, C. Musikas, and P. Vitorge, Eur. Patent Appl. 70,226; Chem. Abstr.,98, 206331 (1983).

    Google Scholar 

  93. C. Musikas, Actinide/Lanthanide Sep., Proc. Int. Symp. (1984), p. 19; Chem. Abstr.,104, 97383 (1986).

  94. X. Vitart, C. Musikas, J. Y. Pasquiou, and P. Hoel, J. Less Common Met.,122, 275 (1986); Chem. Abstr.,105, 230344 (1986).

    Google Scholar 

  95. T. Okutani, Y. Oishi, K. Uchida, and N. Arai, Nippon Kagaku Kaishi, No. 7, 853 (1986); Chem. Abstr.,105, 145145 (1986).

    Google Scholar 

  96. B. K. Puri, M. Satake, G. Kano, and S. Usami, Anal. Chem.,59, 1850 (1987); Chem. Abstr.,107, 50990 (1987).

    Google Scholar 

  97. W. C. Hoyle and J. Benga, Talanta,27(11B), 963 (1980); Chem. Abstr.,94, 135331 (1981).

    Google Scholar 

  98. H. Kato, S. Tomura, and Y. Wada, Jpn. Pat. Appl. 79,159,383; Chem. Abstr.,93, 35032 (1980).

    Google Scholar 

  99. S. Yasuda, T. Kurohara, and A. Taguro, British Patent Appl. 2,095,253; Chem. Abstr.,98, 7905 (1983).

    Google Scholar 

  100. H. Kagawa, Jpn. Pat. Appl. 61,133,227; Chem. Abstr.,106, 68436 (1987).

    Google Scholar 

  101. Fuji-Xerox Co., Jpn. Pat. Appl. 57,171,343; Chem. Abstr.,99, 222378 (1983).

    Google Scholar 

  102. J. L. Lin, M. Satake, and B. K. Puri, Analysis,13, 141 (1985); Chem. Abstr.,102, 230982 (1985).

    Google Scholar 

  103. T. Nagahiro, K. Uesugi, M. Satake, and B. K. Puri, Bull. Chem. Soc. Jpn.,58, 1115 (1985); Chem. Abstr.,102, 230998 (1985).

    Google Scholar 

  104. T. Nagashiro, M. Satake, and B. K. Puri, Indian J. Chem. Sect. A,25A, 99 (1986); Chem. Abstr.,105, 17316 (1986).

    Google Scholar 

  105. M. C. Mehra, T. Nagahiro, and M. Satake, Microchem. J.,33, 198 (1986); Chem. Abstr.,105, 34724 (1986).

    Google Scholar 

  106. J. L. Lin, J. Chin. Chem. Soc.,31, 395 (1984); Chem. Abstr.,102, 231038 (1985).

    Google Scholar 

  107. T. Sakai, N. Ohno, N. Ichinobe, and H. Sasaki, Anal. Chim. Acta,221, 109 (1989); Chem. Abstr.,112, 68943 (1990).

    Google Scholar 

  108. T. Nagahiro, M. Satake, B. K. Puri, and J. L. Lin, Microchim. Acta,1, 85 (1984); Chem. Abstr.,100, 95754 (1984).

    Google Scholar 

  109. T. Nagahiro, K. Uesugi, M. C. Mehra, and M. Satake, Talanta,31, 1112 (1984); Chem. Abstr.,102, 71944 (1985).

    Google Scholar 

  110. S. Tsurubou and T. Sakai, Analyst,109, 1397 (1984); Chem. Abstr.,102, 105280 (1985).

    Google Scholar 

  111. F. E. Smith, J. Herbert, J. Gaudin, D. Henessy, and G. R. Reid, Clin. Biochem.,17, 306 (1984); Chem. Abstr.,102, 2800 (1985).

    Google Scholar 

  112. P. Fossati, H. Heidenreich, K. Wehling, and H. Hugl, European Patent Appl. 331,065; Chem. Abstr.,112, 232275 (1990).

    Google Scholar 

  113. T. Sakai, N. Ohno, T. Mori, and H. Sasaki, Bunseki Kagaku,37, 488 (1988); Chem. Abstr.,109, 176300 (1988).

    Google Scholar 

  114. S. Tsurubou and T. Sakai, Bunseki Kagaku,33, 139 (1984); Chem. Abstr.,100, 202606 (1984).

    Google Scholar 

  115. L. L. Stookey, Anal Chem.,42, 779 (1970).

    Google Scholar 

  116. J. D. Artiss, D. R. Strandbergh, and B. Zak, Microchem. J.,28, 275 (1983); Chem. Abstr.,98, 194474 (1983).

    Google Scholar 

  117. Toshiba Corp., Jpn. Pat. Appl. 59,211,564; Chem. Abstr.,102, 135950 (1985).

    Google Scholar 

  118. T. Nagahiro, K. Uesugi, and M. Satake, Anal. Sci.,1, 359 (1985); Chem. Abstr.,104, 141262 (1986).

    Google Scholar 

  119. G. Denti, S. Campagna, L. Sabatino, S. Serroni, M. Ciano, and V. Balzani, Inorg. Chem.,29, 4750 (1990); Chem. Abstr.,113, 223397 (1990).

    Google Scholar 

  120. K. I. Zamaraev and V. N. Parmon, Usp. Khim.,52, 1433 (1983); Russ. Chem. Rev.,52, 817 (1983).

    Google Scholar 

  121. F. P. Rotzinger, S. Munavalli, P. Comte, J. K. Hurst, M. Gratzel, F. J. Pern, and A. J. Frank, J. Am. Chem. Soc.,109, 6619 (1987).

    Google Scholar 

  122. I. Willner, R. Maidan, D. Mandler, H. Dürr, C. Dörr, and K. Zengerle, J. Am. Chem. Soc.,109, 6080 (1987).

    Google Scholar 

  123. J. F. Knifton, US Patent No. 4,605,677; Chem. Abstr.,105, 174807 (1986).

    Google Scholar 

  124. A. Yamamoto, K. Morifuji, S. Ikeda, T. Saito, Y. Uchida, and A. Misano, J. Am. Chem. Soc.,90, 1878 (1968).

    Google Scholar 

  125. G. W. Gokel, Crown Ethers and Cryptands, Royal Soc. Chem. (1994), pp. 55, 167.

  126. D. Luneau, J. Laugier, P. Rey, G. Ulrich, R. Ziessel, P. Legoli, and M. Drillon, J. Chem. Soc. Chem. Commun., No. 6, 741 (1994).

    Google Scholar 

  127. W. Sliwa, L. Chrzastek, and M. Mielniczak, Heterocycles,36, 1645 (1993).

    Google Scholar 

  128. P. D. Beer and P. D. Rotin, J. Chem. Soc. Chem. Commun., No. 1, 52 (1988).

    Google Scholar 

  129. K. T. Potts, K. A. G. Raiford, and K. M. Keshavarz, J. Am. Chem. Soc.,115, 2793 (1993).

    Google Scholar 

  130. J. M. Lehn and A. Rigault, Angew. Chem. Int. Ed.,27, 1095 (1988).

    Google Scholar 

  131. J. M. Lehn and J. B. R. de Vains, Helv. Chim. Acta,75, 1221 (1992).

    Google Scholar 

  132. T. M. Garrett, U. Koert, J. M. Lehn, A. Rigault, D. Meyer, and J. Fischer, J. Chem. Soc. Chem. Commun., No. 7, 557 (1990).

    Google Scholar 

  133. M. Bessonov, M. M. Koton, V. V. Kudryavtsev, and L. A. Laius, Polyimides — a Group of Thermally Stable Polymers [in Russian], Nauka, Leningrad (1983).

    Google Scholar 

  134. V. V. Korshak, A. L. Rusanov, and I. Batirov, News in the Region of Thermally Stable Polymers [in Russian], Donish, Dushanbe (1986).

    Google Scholar 

  135. V. V. Korshak and A. L. Dushanbe, Usp. Khim.,52, 812 (1983).

    Google Scholar 

  136. D. Wilson, H. D. Stenzenberger, and P. M. Hergenrother (eds.), Polyimides, Blackie, Glasgow, London (1990).

    Google Scholar 

  137. M. M. Koton, Vysokomol. Soed.,13A, 1348 (1971).

    Google Scholar 

  138. M. M. Koton, V. P. Mamaev, V. V. Kudryavtsev, E. M. Nekrasova, V. P. Borovik, T. K. Meleshko, V. N. Artem'eva, and E. N. Dergacheva, Zh. Prikl. Khim.,60, 1851 (1987).

    Google Scholar 

  139. M. M. Koton, V. P. Mamaev, A. M. Dubnova, and E. M. Nekrasova, Vysokomol. Soed.,20B, 792 (1978).

    Google Scholar 

  140. V. P. Mamaev, V. P. Borovik, M. M. Koton, T. M. Kiseleva, E. M. Nekrasova, E. N. Dergacheva, S. N. Nikolaeva, and G. N. Fedorova, Vysokomol. Soed.,25B, 102 (1983).

    Google Scholar 

  141. Yu. N. Sazanov, G. N. Fedorova, E. M. Nekrasova, and T. M. Kiseleva, Vysokomol. Soed.,25A, 949 (1983).

    Google Scholar 

  142. V. P. Mamaev, V. P. Borovik, M. M. Koton, and E. M. Nekrasova, Inventor's Certificate No. 853,316; Byul. Izobret., No. 44, 271 (1985).

    Google Scholar 

  143. M. M. Koton, V. V. Kudryavtsev, V. N. Artem'eva, E. M. Nekrasov, V. P. Slizkova, T. A. Maricheva, N. D. Kozhurnikova, L. A. Laius, I. V. Gofman, E. N. Dergacheva, V. E. Smirnova, Yu. N. Sazanov, G. N. Fedorova, O. P. Shkurko, and V. P. Borovik, Russian Federation Patent No. 2,034,862; Byul. Izobret., No. 13, 184 (1995).

    Google Scholar 

  144. G. M. Mikhailov, L. N. Korzhavin, V. V. Kudryavtsev, M. M. Koton, T. A. Maricheva, M. A. Ivanova, N. V. Bobrova, S. V. Bronnikov, N. A. Grigor'eva, O. P. Shkurko, V. P. Borovik, S. M. Yakopson, and O. S. Karchmarchik, Russian Federation Patent No. 2,034,861; Byull. Izobret., No. 13, 184 (1995).

    Google Scholar 

  145. V. N. Artem'eva, V. V. Kudryavtsev, E. M. Nekrasova, V. P. Slizkova, Yu. G. Baklagina, N. V. Lukasheva, O. P. Shkurko, and V. P. Borovik, Izv. Akad. Nauk. Ser. Khim., No. 10, 2288 (1992).

    Google Scholar 

  146. V. N. Artem'eva, V. V. Kudryavtsev, E. M. Nekrasova, V. P. Slizkova, L. A. Shibaev, N. G. Stepanov, Yu. N. Sazanov, G. N. Fedorova, O. P. Shkurko, and V. P. Borovik, Izv. Akad. Nauk. Ser. Khim., No. 10, 2297 (1992).

    Google Scholar 

  147. D. M. Mognonov, V. P. Borovik, L. D. Radnaeva, S. O. Botoeva, O. P. Shkurko, and A. A. Izynev, Sibirsk. Khim. Zh., No. 4, 99 (1991).

    Google Scholar 

  148. Y. Yamazaki, T. Ishikawa, T. Suzuki, and Y. Irie, Nippon Kagaku Kaishi, No. 3, 502 (1976); Chem. Abstr.,85, 6434 (1976).

    Google Scholar 

  149. T. Teshirogi, Jpn. Pat. Appl. 0,348,666; Chem. Abstr.,115, 49064 (1991).

    Google Scholar 

  150. R. Seltzer and D. A. Gordon, US Patent No. 3,729,448; Ref. Zh. Khim., 4S 362 (1974).

    Google Scholar 

  151. R. Seltzer, D. A. Gordon, and P. D. Sherman, US Patent No. 3,814,719; Ref. Zh. Khim., 10S 363 (1975).

    Google Scholar 

  152. R. Seltzer and D. A. Gordon, German Patent No. 2,321,527; Chem. Abstr.,80, 83918 (1974).

    Google Scholar 

  153. É. S. Avanesyan, V. N. Zaplishnyi, and G. M. Pogosyan, Arm. Khim. Zh.,31, No. 8, 627 (1978).

    Google Scholar 

  154. V. V. Korshak, V. P. Mamaev, S. V. Vinogradova, Ya. S. Vygodskii, and E. P. Fokin, Inventor's Certificate No. 267,893; Byull. Izobret., No. 13, 71 (1970).

    Google Scholar 

  155. R. Pfaendner, J. P. Wolf, and K. Hoffmann, German Patent No. 4,237,768; Chem. Abstr.,120, 77946 (1994).

    Google Scholar 

  156. C. Paal and C. Demeler, Berichte,30, 1499 (1897).

    Google Scholar 

  157. K. Yamaguchi, Y. Yoshikawa, K. Sugimoto, Y. Tanabe, and A. Yamaguchi, European Patent Appl. 282,658; Chem. Abstr.,110, 95968 (1989).

    Google Scholar 

  158. K. Kurita and R. L. Williams, J. Polym. Sci. Polym. Chem. Ed.,11, 3125 (1973); Chem. Abstr.,81, 25974 (1974).

    Google Scholar 

  159. K. Kurita and R. L. Williams, J. Polym. Sci. Polym. Chem. Ed.,12, 1809 (1974); Chem. Abstr.,82, 58168 (1975).

    Google Scholar 

  160. M. M. Koton, T. M. Kiseleva, T. I. Zhukova, S. N. Nikolaeva, L. A. Laius, and Yu. N. Sazanov, Vysokomol. Soed.,23A, 1736 (1981).

    Google Scholar 

  161. L. H. Li (ed.), Adhesives and Adhesion Joints [Russian translation], Mir, Moscow (1988), p. 81.

    Google Scholar 

  162. R. Singh and A. S. Hay, Macromolecules,25, 1025 (1992); Chem. Abstr.,116, 60138 (1992).

    Google Scholar 

  163. S. Kondo, M. Kadowaki, M. Mase, T. Kakuno, and Y. Yuki, J. Macromol. Sci. Pure Appl. Chem.,30A, 315 (1993); Chem. Abstr.,118, 102651 (1993).

    Google Scholar 

  164. S. Sako, Jpn. Pat. Appl. 03,107,986; Chem. Abstr.,116, 117133 (1992).

    Google Scholar 

  165. N. Sawa, N. Kato, T. Masuda, S. Miura, and T. Suzuki, Jpn. Pat. Appl. 03,284,675; Chem. Abstr.,116, 235660 (1992).

    Google Scholar 

  166. T. Yamamoto, T. Maruyama, Z.-h. Zhou, T. Ito, T. Fukuda, Y. Yoneda, F. Begum, T. Ikeda, S. Sasaki, H. Takezoe, A. Fukuda, and K. Kubota, J. Am. Chem. Soc.,116, 4832 (1994).

    Google Scholar 

  167. H. Nagasaka and K. Ohta, European Patent Appl. 379200; Chem. Abstr.,114, 33166 (1991).

    Google Scholar 

  168. J. D. Coyle, A. M. Horton, R. S. Davidson, R. Bowser, and P. M. Morgan, European Patent Appl. 389,236; Chem. Abstr.,114, 218124 (1991).

    Google Scholar 

  169. H. Nagasaka and K. Ohta, Jpn. Pat. Appl. 02,189,548; Chem. Abstr.,114, 52934 (1991).

    Google Scholar 

  170. M. Oie, M. Kawada, and T. Yamada, Jpn. Pat. Appl. 03,107,164; Chem. Abstr.,115, 244064 (1991).

    Google Scholar 

  171. M. Hirose, Jpn. Pat. Appl. 03,154,058; Chem. Abstr.,116, 31460 (1992).

    Google Scholar 

  172. Y. Adachi, H. Nakai, T. Akiyama, M. Sasaki, and J. Nakamura, Jpn. Pat. Appl. 0,459,657; Chem. Abstr.,117, 160973 (1992).

    Google Scholar 

  173. N. Kita and M. Koike, German Patent No. 3,822,909; Chem. Abstr.,110, 183029 (1989).

    Google Scholar 

  174. G. Buhr, German Patent No. 3,337,024; Chem. Abstr.,103, 96424 (1985).

    Google Scholar 

  175. E. D. Laganis, G. K. Lalka, and W. K. Smothers, PCT Int. Patent Appl. 9,214,765; Chem. Abstr.,118, 171074 (1993).

    Google Scholar 

  176. M. Miyabe, H. Kohara, and T. Nakayama, German Patent No. 3,939,186; Chem. Abstr.,114, 72343 (1991).

    Google Scholar 

  177. Y. Takeda, M. Miyabe, and T. Nakayama, Jpn. Pat. Appl. 02,217,855; Chem. Abstr.,114, 111918 (1991).

    Google Scholar 

  178. H. Nakai, S. Goto, K. Kishida, and K. Naito, Jpn. Pat. Appl. 03,225,343; Chem. Abstr.,117, 58950 (1992).

    Google Scholar 

  179. T. Usami and T. Shimomura, Jpn. Pat. Appl. 0,321,495; Chem. Abstr.,115, 73775 (1991).

    Google Scholar 

  180. K. Imai and T. Asano, Jpn. Pat. Appl. 04,182,650; Chem. Abstr.,117, 242891 (1992).

    Google Scholar 

  181. K. Iwakura and H. Matsumoto, Jpn. Pat. Appl. 04,195,044; Chem. Abstr.,118, 49448 (1993).

    Google Scholar 

Download references

Authors
  1. V. P. Borovik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. P. Shkurko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Novosibirsk Institute of Organic Chemistry. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1011–1029, August, 1997.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Borovik, V.P., Shkurko, O.P. Properties and application of aryl-substituted azines (review). Chem Heterocycl Compd 33, 883–897 (1997). https://doi.org/10.1007/BF02253156

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02253156

Keywords

Search

Navigation