Skip to main content
Log in

Advances in the chemistry of hydrazinopyrimidines (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Research on methods for the preparation of hydrazinopyrimidines is reviewed. Ways to use hydrazinopyrimidines in the chemistry of pyrimidine and condensed systems that contain a pyrimidine ring and in the synthesis of polydentate ligands are examined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. V. P. Mamaev (editor), Pyrimidines. Tables of Compounds of the Pyrimidine Series [in Russian], Izd. Novosibirsk. Inst. Org. Khim. Sibirsk. Otd. Akad. Nauk SSSR, Novosibirsk (1976).

    Google Scholar 

  2. D. J. Brown, The Pyrimidines, Wiley, New York (1962).

    Google Scholar 

  3. J. F. Tinker, US Patent No. 2852375; Chem. Abstr., 53, 3956 (1959).

    Google Scholar 

  4. J. Schwindt, West German Patent No. 2603834; Chem. Abstr., 87, 152725 (1977).

    Google Scholar 

  5. R. L. Wear, US Patent No. 3087910; Chem. Abstr., 59, 11535 (1963).

    Google Scholar 

  6. D. Shiho and N. Takahayashi, Nippon Kagaku Zasshi, 76, 877 (1955); Chem. Abstr., 51, 17930 (1957).

    Google Scholar 

  7. N. Saha and S. K. Kar, J. Inorg. Nucl. Chem., 39, 195 (1977).

    Google Scholar 

  8. S. Hiroshi, A. Hiroshi, F. Kimio, O. Haruo, and I. Yoichi, Chem. Pharm. Bull., 25, 2267 (1977).

    Google Scholar 

  9. S. Hiroshi, A. Hiroshi, F. Tadao, and S. Takeichi, Chem. Pharm. Bull., 25, 1555 (1977).

    Google Scholar 

  10. S. Hiroshi, A. Hiroshi, F. Kimio, O. Haruo, and I. Yoichi, Chem. Pharm. Bull., 27, 1871 (1979).

    Google Scholar 

  11. R. G. Anderson and G. Nickless, Talanta, 14, 1221 (1967).

    Google Scholar 

  12. R. G. Anderson and G. Nickless, Analyst, 93, 20 (1968).

    Google Scholar 

  13. A. V. Ivashchenko, O. V. Ivanov, and V. M. Dziomko, USSR Inventor's Certificate No. 588225; Byull. Izobret., No. 2, 75 (1978).

  14. A. V. Ivashchenko, B. E. Zaitsev, S. V. Krikunova, and R. V. Poponova, Khim. Geterotsikl. Soedin., No. 12, 1682 (1980).

    Google Scholar 

  15. A. V. Ivashchenko, O. V. Ivanov, and V. M. Dziomko, USSR Inventor's Certificate No. 600139; Byull. Izobret., No. 12, 99 (1978).

  16. A. V. Ivashchenko and V. M. Dziomko, USSR Inventor's Certificate No. 698984; Byull. Izobret., No. 43, 91 (1979).

  17. A. V. Ivashchenko, V. M. Dziomko, and O. V. Ivanov, in: Synthesis and Investigation of Inorganic Compounds in Nonaqueous Media. Summaries of Papers Presented at the 3rd All-Union Conference, Rostov-on-Don [in Russian], Part 1 (1976), p. 89.

  18. A. V. Ivashchenko, V. M. Dziomko, and O. V. Ivanov, in: Synthesis and Investigation of Inorganic Compounds in Nonaqueous Media. Summaries of Papers Presented at the 3rd All-Union Conference, Rostov-on-Don [in Russian], Part 1 (1976), p. 90.

  19. V. P. Podalko, A. V. Ivashchenko, A. P. Bogdanov, and V. V. Zelentsov, in: Synthesis and Investigation of Inorganic Compounds in Nonaqueous Media. Summaries of Papers Presented at the 3rd All-Union Conference, Rostov-on-Don [in Russian], Part 2 (1976), p. 35.

  20. V. M. Dziomko, V. N. Avilina, A. V. Ivashchenko, and L. I. Nikol'skaya, in: Organic Reagents in Analytical Chemistry. Summaries of Papers Presented at the 4th All-Union Conference, Kiev [in Russian], Part 1 (1976), p. 26.

  21. A. V. Ivashchenko and V. M. Dziomko, Khim. Geterotsikl. Soedin., No. 9, 1255 (1977).

    Google Scholar 

  22. A. V. Ivashchenko and V. M. Dziomko, Khim. Geterotsikl. Soedin., No. 10, 1404 (1977).

    Google Scholar 

  23. A. V. Ivashchenko, A. P. Bogdanov, V. M. Dziomko, V. V. Zelentsov, and V. V. Titov, Koordinats. Khim., 4, 1712 (1978).

    Google Scholar 

  24. A. V. Ivashchenko, O. V. Ivanov, A. I. Vasil'ev, V. P. Pogareva, and V. M. Dziomko, Koord. Khim., 3, 553 (1977).

    Google Scholar 

  25. A. V. Ivashchenko, O. N. Garicheva, A. P. Bogdanov, and V. M. Dziomko, Summaries of Papers Presented at the 3rd All-Union Chugaev Conference on the Chemistry of Complexes [in Russian], Nauka, Moscow (1978), p. 166.

    Google Scholar 

  26. A. V. Ivashchenko and O. N. Garicheva, Reactivity of Azines. Scientific-Technical Ref. Sb., Novosibirsk [in Russian], Izd. Novosibirsk. Inst. Org. Chem., Siberian Branch. Academy of Sciences of the USSR (1979), p. 99.

  27. A. V. Ivashchenko, O. N. Garicheva, and A. P. Bogdanov, Proceedings of the 19th International Conference on Coordination Chemistry, Prague (1978), Supplement, p.2.

  28. A. V. Ivashchenko, O. N. Garicheva, Yu. S. Ryabokobylko, and L. V. Shemelv, News in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Vol. 2, Zinatne, Riga (1979), p. 138.

    Google Scholar 

  29. A. V. Ivashchenko, O. N. Garicheva, L. V. Shmelev, and Yu. S. Ryabokobylko, Khim. Geterotsikl. Soedin., No. 3, 404 (1980).

    Google Scholar 

  30. Imperial Chemical Industries Ltd., French Patent No. 1572620; Chem. Abstr., 72, 132773 (1970).

    Google Scholar 

  31. CIBA Ltd., French Patent No. 1332539; Chem. Abstr., 60, 2981 (1964).

    Google Scholar 

  32. T. K. Ryabukha and A. A. Pisarev, Farmakol. Toksikol., 35, 82 (1972).

    Google Scholar 

  33. N. R. Cozarelli, R. L. Low, S. A. Rashbaum, and C. L. Peebles, JCN-UCLA Symp. Mol. Cell. Biol., 1975, Vol. 3 (DNA Synth. and Its Regul.), p. 18; Chem. Abstr., 84, 86035 (1976).

    Google Scholar 

  34. B. C. P. Chu, D. M. Brown, and M. G. Burdon, Mutat. Res., 23, 627 (1974); Chem. Abstr., 83, 72573 (1975).

    Google Scholar 

  35. A. A. Aroyan, M. S. Kramer, V. T. Garybdzhanyan, and G. M. Stepanyan, Arm. Khim. Zh., 22, 617 (1969).

    Google Scholar 

  36. G. W. Gamilner, Biochem. Pharmacol., 16, 1691 (1967).

    Google Scholar 

  37. G. J. Stacey, West German Patent No. 2018550; Chem. Abstr., 74, 22873 (1971).

    Google Scholar 

  38. K. J. Rorig and H. A. Wagner, US Patent No. 3412094; Chem. Abstr., 70, 68410 (1969).

    Google Scholar 

  39. S. Ozawa, Kyoto Daigaku Kekkaku-Kenkyusho Nempo, 4, 295 (1956); Chem. Abstr., 51, 5899 (1957).

    Google Scholar 

  40. H. Akio, S. Mineo, and K. Kasuo, Oyo Yakuri, 5, 441 (1971); Chem. Abstr., 76, 68252 (1972).

    Google Scholar 

  41. H. Akio, S. Mineo, and K. Kasuo, Oyo Yakuri, 6, 1071 (1972); Chem. Abstr., 78, 92407 (1973).

    Google Scholar 

  42. K. Shirakawa, Yakugaku Zasshi, 79, 1477 (1959); Chem. Abstr., 54, 11038 (1969).

    Google Scholar 

  43. B. Presott, Int. J. Clin. Pharmacol. Biopharmacol., 11, 332 (1975).

    Google Scholar 

  44. J. Mustea, Int. J. Radiat. Biol., 23, 409 (1973).

    Google Scholar 

  45. R. G. Glushkov, E. G. Sochilin, and B. A. Ivin, Zh. Obshch. Khim., 39, 924 (1969).

    Google Scholar 

  46. K. Wempen, N. Miller, E. A. Talco, and J. J. Fox, J. Med. Chem., 11, 144 (1968).

    Google Scholar 

  47. K. L. Nagpal, J. Med. Chem., 15, 121 (1972).

    Google Scholar 

  48. W. Schuler and E. Wyss, Arch. Intern. Pharmacodyn., 128, 431 (1960); Chem. Abstr., 55, 11654 (1961).

    Google Scholar 

  49. G. E. Wright and N. C. Brown, J. Med. Chem., 17, 1277 (1974).

    Google Scholar 

  50. J. E. Chments, J. D'Ambrosio, and N. C. Brown, J. Biol. Chem., 250, 525 (1975).

    Google Scholar 

  51. F. P. Trunus and T. K. Ryabukha, Farmakol. Toksikol., 36, 84 (1973).

    Google Scholar 

  52. F. P. Trunus, V. A. Portnyagina, T. K. Ryabukha, and V. K. Karn, Farmakol. Toksikol., 31, 37 (1968).

    Google Scholar 

  53. M. Ganuly, D. Sen, and B. C. Guha, Naturwissenschafften, 48, 695 (1961).

    Google Scholar 

  54. D. Liebermann, French Patent No. 1170115; Chem. Abstr., 54, 21147 (1959).

    Google Scholar 

  55. A. A. Aroyan, M. A. Kaldrikyan, and L. A. Grigoryan, Armyansk. Khim. Zh., 22, 401 (1969).

    Google Scholar 

  56. N. Sahero, A. Sotoo, H. Tadamitsu, and N. Katsuo, Japanese Patent No. 7222583; Chem. Abstr., 77, 101651 (1972).

    Google Scholar 

  57. A. A. Urbanas, T. V. Valentukhyavichne, G. D. Vitenaite, K. Yu. Nazitskaite, and L. L. Yasinskas, Khim. Tekhnol., No. 14, 153 (1972).

    Google Scholar 

  58. F. Reicheneder and K. L. Hock, West German Patent No. 1921340; Chem. Abstr., 74, 57318 (1971).

    Google Scholar 

  59. K. J. M. Andrews and B. P. Tong, US Patent No. 3813393; Chem. Abstr., 81, 49706 (1974).

    Google Scholar 

  60. N. Takeo, Y. Toru, K. Shinichi, and A. Naoemon, Chem. Pharm. Bull., 17, 1467 (1969).

    Google Scholar 

  61. N. Takeo, O. Yasuo, Y. Toru, K. Akira, D. Renzo, N. Yoshiaki, and T. Wataru, South African Patent No. 6704936; Chem. Abstr., 70, 57876 (1969).

    Google Scholar 

  62. O. Yasuo, A. Takeshi, T. Wataru, Y. Terukiyo, Y. Kunio, and K. Hiroshi, Chem. Pharm. Bull., 17, 1492 (1969).

    Google Scholar 

  63. N. Takehiko and F. Sumiyosu, Japanese Patent No. 77105194; Chem. Abstr., 88, 105396 (1978).

    Google Scholar 

  64. T. K. Ryabukha, Pharmacol. Toksikol., 33, 199 (1970).

    Google Scholar 

  65. Imperial Chemical Industries Ltd., British Patent No. 876601; Chem. Abstr., 56, 4781 (1962).

    Google Scholar 

  66. M. Shinsaku, F. Akio, F. Katsuro, and T. Yashiyuki, Japanese Patent No. 43451 ('67); Chem. Abstr., 67, 21928 (1967).

    Google Scholar 

  67. S. Shigeo and H. Kosaku, Chem. Pharm. Bull., 22, 1459 (1974).

    Google Scholar 

  68. K. Ueno, T. Moroi, H. Kojima, and T. Chiba, Japanese Patent No. 7411705; Chem. Abstr., 81, 91517 (1974).

    Google Scholar 

  69. K. Shirakawa, US Patent No. 3040047; Chem. Abstr., 58. 533 (1963).

    Google Scholar 

  70. K. Shirakawa, Japanese Patent No. 603032; Chem. Abstr., 55, 1669 (1961).

    Google Scholar 

  71. K. Shirakawa, Japanese Patent No. 4492 ('64); Chem. Abstr., 61, 5666 (1964).

    Google Scholar 

  72. K. Shirakawa, Japanese Patent No. 4493 ('64); Chem. Abstr., 61, 5666 (1964).

    Google Scholar 

  73. K. Shirakawa, Japanese Patent No. 4491 ('64); Chem. Abstr., 61, 5667 (1964).

    Google Scholar 

  74. K. Shirakawa and T. Tsujikawa, Japanese Patent No. 5040 ('64); Chem. Abstr., 61, 7025 (1964).

    Google Scholar 

  75. H. C. Koppel, R. H. Springer, G. D. Daves, and C. C. Cheng, J. Pharm. Sci., 52, 81 (1963).

    Google Scholar 

  76. K. Shirakawa and T. Tsujikawa, Kenkyusho Nempo, 22, 19 (1963); Chem. Abstr., 60, 12009 (1964).

    Google Scholar 

  77. Recherche et Industrie Therapeutiques, Belgian Patent No. 56109; Chem Abstr., 54, 2376 (1960).

    Google Scholar 

  78. P. J. Dijik, M. Clacsen, H. Vanderhaeghe, and P. de Somer, Antibiotics Chemotherapy, 9, 523 (1959).

    Google Scholar 

  79. K. Shirakawa and T. Tsujikawa, Takeda Kenkyusho Nempo, 22, 27 (1963); Chem. Abstr., 60, 1209 (1964).

    Google Scholar 

  80. G. W. Miller and W. R. Wragg, British Patent No. 864731; Chem. Abstr., 55, 24798 (1961).

    Google Scholar 

  81. E. C. Taylor, J. W. Barton, and W. W. Paudler, J. Org. Chem., 26, 4961 (1961).

    Google Scholar 

  82. A. Tujita, T. Yamamoto, S. Minami, and H. Takamatsu, Chem. Pharm. Bull., 13, 1183 (1965).

    Google Scholar 

  83. H. Berger, R. Cyall, H. Merdes, K. Stach, W. Sauer, and W. Voemel, West German Patent No. 1909346; Chem. Abstr., 73, 98974 (1970).

    Google Scholar 

  84. C. J. Temple, C. L. Kussner, and J. A. Montgomery, J. Org. Chem., 36, 3502 (1971).

    Google Scholar 

  85. S. Tadashi and A. Moriyasu, Yuked Goei Kagaku Kyokai Sci., 27, 1969 (1969); Chem. Abstr., 7l, 22101 (1969).

    Google Scholar 

  86. I. Hirao, T. Fujimoto, Y. Kato, and H. Okazaki, Kogyo Kagaku Zasshi, 66, 1682 (1963); Chem. Abstr., 60, 12608 (1964).

    Google Scholar 

  87. M. E. C. Biffin, D. J. Brown, and T. Sugimoto, J. Chem. Soc., C, No. 1, 139 (1970).

    Google Scholar 

  88. L. Gimmanco, Atti. Acad. Sci., Lett. Arti Palermo, Parte I, 27, 449 (1968); Chem. Abstr., 72, 21673 (1970).

    Google Scholar 

  89. H. Yamamoto, M. Nakata, S. Morosawa, and A. Yakoo, Bull. Chem. Soc. Jap., 44, 153 (1971).

    Google Scholar 

  90. Y. Tumio, N. Tomohisa, and J. Misuzu, J. Heterocycl. Chem., 11, 83 (1974).

    Google Scholar 

  91. B. K. Billinys, I. A. Wagner, P. D. Cook, and R. N. Gastle, J. Heterocycl. Chem., 12, 1221 (1975).

    Google Scholar 

  92. G. C. Tsatsaronis, A. H. Kehayoglou, and H. C. Andria, Rec. Trav. Chim., 90, 584 (1971).

    Google Scholar 

  93. D. J. Brown and R. K. Lynn, Aust. J. Chem., 27, 1781 (1974).

    Google Scholar 

  94. H. C. van der Plas, B. Haase, B. Zuurdeeg, and M. C. Vollering, Rec. Trav. Chim., 85, 1101 (1968).

    Google Scholar 

  95. R. R. Schmidt, Chem. Ber., 98, 346 (1965).

    Google Scholar 

  96. H. Bredereck, G. Simchen, and H. Traut, Chem. Ber., 100, 3664 (1967).

    Google Scholar 

  97. W. H. Nyberg and C. C. Cheng, J. Heterocycl. Chem., 1, 1 (1961).

    Google Scholar 

  98. Y. Fumia and N. Tomohisa, Synthesis, No. 1, 177 (1975).

    Google Scholar 

  99. C. J. Temple, J. R. L. McKee, and J. A. Montgomery, J. Org. Chem., 28, 932 (1963).

    Google Scholar 

  100. J. A. Montgomery and C. J. Temple, J. Am. Chem. Soc., 82, 4592 (1960).

    Google Scholar 

  101. W. Broadbent, L. A. McArdle, and F. L. Roze, J. Chem. Soc., C, No. 5, 1689 (1969).

    Google Scholar 

  102. M. Hauser, E. Petess, and H. Tickelmann, J. Org. Chem., 25, 1570 (1960).

    Google Scholar 

  103. K. Takagi and T. Ueda, Chem. Pharm. Bull., 11, 1382 (1963).

    Google Scholar 

  104. Y. Tumio, N. Tettuya, and K. Mitsuko, Chem. Commun., No. 6, 658 (1976).

    Google Scholar 

  105. G. Tsatsaronis and F. Effenberger, Chem. Ber., 94, 2876 (1961).

    Google Scholar 

  106. O. Nagase, M. Hirata, and M. Inaoka, Yakugaku Zasshi, 82, 528 (1962); Chem. Abstr., 58, 3430 (1963).

    Google Scholar 

  107. C. J. Temple, L. B. Smith, and J. A. Montgomery, J. Org. Chem., 33, 530 (1968).

    Google Scholar 

  108. W. Kummer, H. Stachle, H. Koeppe, and K. Leile, South African Patent No. 6800417; Chem. Abstr., 68, 372 (1968).

    Google Scholar 

  109. T. Naito, Nagaseo, M. Hirata, and S. Okada, Japanese Patent No. 20577 ('63); Chem. Abstr., 60, 2976 (1964).

    Google Scholar 

  110. N. Takeo, N. Osamu, and H. Miyoshi, Japanese Patent No. 10793 ('62); Chem. Abstr., 59, 3339 (1963).

    Google Scholar 

  111. V. V. der Raegle and M. Claesen, Bull. Soc. Chim. Belg., 68, 30 (1959).

    Google Scholar 

  112. G. W. Miller and E. P. Rose, J. Chem. Soc., No. 12, 5642 (1963).

    Google Scholar 

  113. M. Hauser, E. Petess, and H. Tiekelmann, J. Org. Chem., 26, 451 (1961).

    Google Scholar 

  114. M. P. L. Katon and J. F. W. McOmil, J. Chem. Soc., C, No. 7, 836 (1968).

    Google Scholar 

  115. B. W. Langley, British Patent No. 854011; Chem. Abstr., 55, 13457 (1961).

    Google Scholar 

  116. B. A. Ivin, R. G. Glushkov, and E. F. Sochilin, Zh. Obshch. Khim., 40, 202 (1970).

    Google Scholar 

  117. J. H. Chesterfield, J. F. W. McOmil, and M. S. Tute, J. Chem. Soc., No 11, 4590 (1960).

    Google Scholar 

  118. T. S. Yates and I. Blair, J. Chem. Soc., Perkins Trans. I, No. 13, 1565 (1974).

    Google Scholar 

  119. D. J. Brown and T. Sugimoto, J. Chem. Soc., C, No. 15, 2616 (1971).

    Google Scholar 

  120. H. G. van der Plas and G. Geurtsen, Tetrahedron Lett., No. 32, 2093 (1964).

    Google Scholar 

  121. H. G. van der Plas, Rec. Trav. Chim., 84, 1101 (1965).

    Google Scholar 

  122. Badische Anilin und Soda Fabrik A.-G., British Patent No. 1174165; Chem. Abstr., 72, 90504 (1970).

    Google Scholar 

  123. M. E. C. Biffin, D. J. Brown, and T. C. Lee, J. Chem. Soc., C, No. 7, 573 (1970).

    Google Scholar 

  124. W. D. Guither, D. G. Clark, and R. N. Castle, J. Heterocycl. Chem., 2, 67 (1965).

    Google Scholar 

  125. R. H. Wiley, J. Lanet, and K. H. Hussung, J. Heterocycl. Chem., 1, 175 (1964).

    Google Scholar 

  126. D. Shiho, S. Tagami, N. Takahayashi, and R. Handa, J. Pharm. Soc. Jpn., 76, 804 (1955); Chem. Abstr. 51, 1196 (1957).

    Google Scholar 

  127. M. E. C. Biffin, D. J. Brown, and T. C. Lee, Austr. J. Chem., 20, 1041 (1967).

    Google Scholar 

  128. L. E. Brady and R. M. Herbst, J. Org. Chem., 24, 922 (1959).

    Google Scholar 

  129. E. Peters, H. J. Minnemeyer, A. V. Spears, and H. Tieckelmann, J. Org. Chem., 25, 2137 (1960).

    Google Scholar 

  130. Farmacentici Italia Soc., Anon., British Patent No. 845552; Chem. Abstr., 55, 6507 (1961).

    Google Scholar 

  131. H. Vanderhaeghe and M. Claesen, Bull. Soc. Chim. Belg., 68, 30 (1959).

    Google Scholar 

  132. Y.-T. Chi and Y.-L. Wu, Hua Hsuch Pao, 23, 145 (1957); Chem. Abstr., 52, 14626 (1957).

    Google Scholar 

  133. Z. Machon and A. Dlugosz, Pol. J. Pharmacol. Pharm., 28, 145 (1976); Chem. Abstr., 52, 14626 (1957).

    Google Scholar 

  134. F. Baumboch, H. G. Henning, and G. Hilgetag, Z. Chem., 4, 67 (1964).

    Google Scholar 

  135. E. Tenor and C. F. Kroeger, Chem. Ber., 97, 1373 (1964).

    Google Scholar 

  136. D. Liberman and A. Rouaix, Bull. Soc. Chim. France, No. 11/12, 1793 (1959).

    Google Scholar 

  137. M. Muchlstaedt, H. I. Krausmann, and G. Tisher, J. Prakt. Chem., 312, 254 (1970).

    Google Scholar 

  138. H. Spänig and H. R. Hensel, West German Patent No. 955507; Chem. Abstr., 53, 4317 (1958).

    Google Scholar 

  139. I. D. Bower and F. D. Doyle, J. Chem. Soc., No. 2, 727 (1957).

    Google Scholar 

  140. A. V. Spasov and Z. D. Paikov, Z. Chem., 11, 260 (1971).

    Google Scholar 

  141. D. J. Brown and T. Sugimoto, J. Chem. Soc., C, No. 19, 2661 (1970).

    Google Scholar 

  142. M. H. Krackov, Dissertation Abstracts, 23, 1927 (1962).

    Google Scholar 

  143. M. H. Krackov and B. E. Christensen, J. Org. Chem., 28, 2677 (1963).

    Google Scholar 

  144. C. J. Temple, C. L. Kussner, and J. A. Montgomery, J. Org. Chem., 34, 2102 (1969).

    Google Scholar 

  145. M. E. C. Biffin and D. J. Brown, Tetrahedron Lett., No. 21, 2503 (1968).

    Google Scholar 

  146. M. E. C. Biffin, D. J. Brown, and Q. N. Porter, Tetrahedron Lett., No. 21, 2029 (1967).

    Google Scholar 

  147. M. E. C. Biffin, D. J. Brown, and Q. N. Porter, J. Chem. Soc., C, No. 17, 2159 (1968).

    Google Scholar 

  148. B. E. Christensen, Q. Stahl, and F. Lehnikuhl, J. Org. Chem., 36, 2462 (1971).

    Google Scholar 

  149. Q. Stahl, Dissertation Abstracts, 30, 2098 (1969).

    Google Scholar 

  150. Z. Budesinaky and J. Varina, Collect Czech. Chem. Commun., 37, 1721 (1972).

    Google Scholar 

  151. N. Saburo, A. Sotoo, Y. Katsumosa, and N. Jun, Japanese Patent No. 7208008; Chem. Abstr., 77, 5518 (1972).

    Google Scholar 

  152. D. J. Brown and J. A. Hoskins, J. Chem. Soc., Perkin Trans. I, No. 4, 522 (1972).

    Google Scholar 

  153. K. Shirakawa, J. Pharm. Soc. Jpn., 73, 635 (1953).

    Google Scholar 

  154. K. Shirakawa, T. Tsujikawa, and T. Tsuda, US Patent No. 3041339; Chem. Abstr., 57, 137 (1962).

    Google Scholar 

  155. A. V. Ivashchenko, O. N. Garicheva, M. F. Kachkovskaya, V. M. Ostrovskaya, L. V. Lomakina, and V. M. Dziomko, USSR Inventor's Certificate No. 791748; Byull. Izobret., No. 48, 96 (1980).

  156. W. Kunze, West German Patent No. 962165; Chem. Abstr., 53, 10262 (1959).

    Google Scholar 

  157. F. Lingens and H. Schneider-Bernloehr, Ann., 686, 134 (1965).

    Google Scholar 

  158. G. B. Barlin and A. C. Young, J. Chem. Soc., Perkin I, No. 10, 1269 (1972).

    Google Scholar 

  159. T. Shiho and N. Takahayashi, Nippon Kagaku Zasshi, 75, 773 (1955); Chem. Abstr., 51, 17930 (1957).

    Google Scholar 

  160. A. Kreutzberger, Chem. Ber., 99, 2237 (1966).

    Google Scholar 

  161. A. Kreutzberger, J. Phys. Chem., 24, 368 (1960).

    Google Scholar 

  162. J. M. Mackenzic, M. H. Neville, G. E. Wright, and N. C. Brown, Proc. Nat. Acad. Sci. USA, 70, 512 (1973).

    Google Scholar 

  163. E. C. Taylor and F. Sowinski, J. Am. Chem. Soc., 90, 1374 (1968).

    Google Scholar 

  164. T. Yoneda, S. Fukazawa, and S. Nishigaki, Chem. Commun., No. 1, 83 (1971).

    Google Scholar 

  165. S. Shigeo, H. Kosaku, and A. Fetsuji, Chem. Pharm. Bull., 23, 1708 (1975).

    Google Scholar 

  166. R. Giuliano and G. Leonardi, Farmaco Ed. Sci., 11, 389 (1956); Chem. Abstr., 53, 10248 (1959).

    Google Scholar 

  167. G. F. Wright, J. Heterocycl. Chem., 14, 701 (1977).

    Google Scholar 

  168. R. S. Shadbolt and T. L. Ulbricht, J. Chem. Soc., C, No. 6, 733 (1968).

    Google Scholar 

  169. J. Hervieu, M. F. Latie-Mouneyras, J. Dagaut, P. Dizabo, L. C. Leitch, and R. N. Renaud, J. Labelled Compounds, 2, 365 (1972); Chem. Abstr., 78, 72043 (1973).

    Google Scholar 

  170. W. Kircor, P. Grudzinska, and E. Kozlowska, Polish Patent No. 64697; Chem. Abstr., 77, 164741 (1972).

    Google Scholar 

  171. L. S. Timonina and V. M. Vvedenskii, Khim. Geterotsikl. Soedin., No. 2, 267 (1973).

    Google Scholar 

  172. I. Kh. Fel'dman and Chih Chung-tsü, Zh. Obshch. Khim., 30, 3832 (1960).

    Google Scholar 

  173. L. Fabbrini, Gazz. Chim. Ital., 87, 1293 (1957).

    Google Scholar 

  174. D. Wojcich and L. Romuald, Acta Polon. Pharm., 25, 221 (1968).

    Google Scholar 

  175. R. G. Glushkov, E. G. Sochilin, and B. A. Ivin, Zh. Obshch. Khim., 37, 1579 (1967).

    Google Scholar 

  176. G. W. Miller and F. L. Rose, British Patent No. 897870; Chem. Abstr., 58, 10211 (1963).

    Google Scholar 

  177. E. S. Karavaeva, N. P. Bednyagina, T. A. Sharkova, and I. I. Mudretsova, Khim. Geterotsikl. Soedin., No. 10, 1420 (1975).

    Google Scholar 

  178. E. S. Karavaeva, T. A. Sharkova, and N. P. Bednyagina, Summaries of Papers Presented at the Scientific-Technical Conference on the Chemical Application of Formazans [in Russian], Sverdlovsk (1974), p. 9.

  179. I. A. Mazur and V. M. Cherkasov, Khim. Geterotsikl. Soedin., No. 10, 1409 (1976).

    Google Scholar 

  180. Y. Nato, T. Yoshikawa, and N. Aoni, Chem. Pharm. Bull., 17, 1467 (1969).

    Google Scholar 

  181. S. Nishigaka, K. Ogiwara, K. Senya, S. Fukazawa, K. Aida, Y. Machida, and T. Yoneda, Chem. Pharm. Bull., 18, 1385 (1970).

    Google Scholar 

  182. M. Yoshio and S. Sadakatsu, Japanese Patent No. 7372177; Chem. Abstr., 79, 137187 (1973).

    Google Scholar 

  183. H. Bredereck, F. Effenberger, and M. Hajek, Chem. Ber., 98, 3178 (1965).

    Google Scholar 

  184. G. Tsatsaronis and F. Effenberger, Chem. Ber., 94, 2876 (1961).

    Google Scholar 

  185. G. Tsatsaronis, G. Karamanlidis, and S. Roussonikolos, Chim. Chronica, 29, 186 (1964).

    Google Scholar 

  186. G. Tsatsaronis, E. Mikromastoras, and S. Halivopoulos, Chim. Chronica, 31, 57 (1966).

    Google Scholar 

  187. K. Nagahara and A. Takada, Heterocycles, 9, 197 (1978).

    Google Scholar 

  188. Dutch Patent No. 7408228; Chem. Abstr., 83, 28273 (1975).

  189. Y. Morita, Y. Samejima, and S. Shimada, Japanese Patent No. 7372176; Chem. Abstr., 79, 137187 (1973).

    Google Scholar 

  190. Ferrer Internacional S. A., Spanish Patent No. 437466; Chem. Abstr., 87, 68412 (1977).

    Google Scholar 

  191. H. Tadamosa and N. Higashi, Japanese Patent No. 75129576; Chem. Abstr., 84, 180254 (1976).

    Google Scholar 

  192. A. Takeshi, T. Wataru, Y. Tarukiyo, K. Hiroshi, K. Akira, Y. Kunio, and O. Yasuo, Nippon Yakurigaku Zasshi, 65, 378 (1969); Chem. Abstr., 73, 97256 (1970).

    Google Scholar 

  193. A. Tobe and K. Umezu, Yakugaku Zasshi, 96, 503 (1976); Chem. Abstr., 85, 72180 (1976).

    Google Scholar 

  194. S. Asai, K. Nakagawa, and T. Hirayama, Japanese Patent No. 7616681; Chem. Abstr., 85, 123961 (1976).

    Google Scholar 

  195. T. Hirayama and K. Nakagawa, Japanese Patent No. 76128987; Chem. Abstr., 86, 171491 (1977).

    Google Scholar 

  196. T. Nishimura, Y. Miyamoto, and H. Fukuyasu, Yakugaku Zasshi, 96, 384 (1976); Chem. Abstr., 85, 355 (1976).

    Google Scholar 

  197. K. Shirakawa, T. Tsujikawa, and T. Tsuda, Japanese Patent No. 12332; Chem. Abstr., 62, 574 (1965).

    Google Scholar 

  198. K. Jamada and K. Asano, Japanese Patent No. 7303630; Chem. Abstr., 78, 147983 (1973).

    Google Scholar 

  199. G. E. Wright and N. C. Brown, J. Med. Chem., 20, 1181 (1977).

    Google Scholar 

  200. I. Ya. Postovskii and N. V. Smirnova, Dokl. Akad. Nauk SSSR, 166, 1136 (1966).

    Google Scholar 

  201. R. Giuliano and G. Leonardi, Farm. Ed. Sci., 12, 394 (1957); Chem. Abstr., 53, 2190 (1959).

    Google Scholar 

  202. V. K. Karp and F. A. Portnyagina, Khim.-Farm. Zh., 4, No. 7, 29 (1970).

    Google Scholar 

  203. P. A. Crans and B. Robinson, Can. J. Chem., 47, 2061 (1969).

    Google Scholar 

  204. S. Senda and K. Hirota, Chem. Lett., No. 5, 367 (1972).

    Google Scholar 

  205. T. D. Duffy and D. G. Wibberley, J. Chem. Soc., Perkin Trans. I, No. 16, 1921 (1974).

    Google Scholar 

  206. R. G. Glushkov, I. M. Zasosova, and I. M. Ovcharova, in: The Chemistry and Pharmacology of Indole Compounds [in Russian], Shtiintsa, Kishinev (1975), p. 77.

    Google Scholar 

  207. G. E. Wright, J. Heterocycl. Chem., 13, 539 (1976).

    Google Scholar 

  208. R. G. Glushkov, I. M. Zasosova, and I. M. Ovcharova, Khim. Geterotsikl. Soedin., No. 10, 1398 (1977).

    Google Scholar 

  209. R. G. Glushkov, V. G. Granik, I. M. Zasosova, O. Ya. Belyaeva, V. G. Smirnova, A. M. Zhidkova, I. M. Ovcharova, and N. V. Marchenko, Summaries of Papers and Communications Presented at the 11th Mendeleev Congress of General and Applied Chemistry [in Russian], Vol. 2, Nauka, Moscow (1975), p. 41.

    Google Scholar 

  210. A. Dornow and K. Dehmer, Chem. Ber., 100, 2577 (1967).

    Google Scholar 

  211. F. Yoneda and T. Nagamatsu, Synthesis, No. 5, 300 (1973).

    Google Scholar 

  212. F. Yoneda, T. Nagamatsu, T. Nagamura, and K. Senda, J. Chem. Soc., Perkin I, No. 7, 765 (1977).

    Google Scholar 

  213. K. Senga, T. Kanamori, M. Kanazawa, and S. Nishigawa, J. Heterocycl. Chem., 15, 359 (1978).

    Google Scholar 

  214. C. Temple, J. R. McKel, and J. A. Montgomery, J. Org. Chem., 27, 1671 (1962).

    Google Scholar 

  215. B. Camerino, G. Polomidessi, and R. Sciaky, Gazz. Chim. Ital., 90, 1821 (1960).

    Google Scholar 

  216. G. W. Miller and F. L. Rose, British Patent No. 859287; Chem. Abstr., 55, 17665 (1961).

    Google Scholar 

  217. Y. Tumio and N. Tomohisa, Chem. Pharm. Bull., 23, 1885 (1975).

    Google Scholar 

  218. K. Senga, Y. Kanamori, S. Nishigaki, and F. Yoneda, Chem. Pharm. Bull., 24, 1917 (1976).

    Google Scholar 

  219. K. Shirakawa, Yakugaku Zasshi, 78, (1958); Chem. Abstr., 53, 8150 (1959).

  220. K. Shirakawa, Japanese Patent No. 3326 ('59); Chem. Abstr., 54, 14278 (1960).

    Google Scholar 

  221. K. Shirakawa, Yakugaku Zasshi, 79, 899 (1959); Chem. Abstr., 54, 556 (1960).

    Google Scholar 

  222. C. F. Allen, H. R. Beilfuss, D. M. Burness, G. A. Reynolds, J. F. Tinker, and J. A.V. Allen, J. Org. Chem., 24, 787 (1959).

    Google Scholar 

  223. C. F. Allen, G. A. Reynolds, J. F. Tinker, and L. A. Williams, J. Org. Chem., 25, 361 (1960).

    Google Scholar 

  224. A. V. Spasov (Spasow), E. V. Golovinskii (Golovinsky), and G. S. Russev (Russew), Z. Chem., 8, 421 (1968).

    Google Scholar 

  225. K. Shirakawa, Yakugaku Zasshi, 80, 952 (1960); Chem. Abstr., 54, 24763 (1960).

    Google Scholar 

  226. H. Berger, R. Gall, H. Merdes, K. Stach, W. Sauer, and W. Voemel, West German Patent No. 2004713; Chem. Abstr., 75, 118338 (1971).

    Google Scholar 

  227. T. Teruaki and T. Motorui, Chem. Pharm. Bull., 25, 3137 (1977).

    Google Scholar 

  228. J. A. Bee and F. L. Rose, J. Chem. Soc., C, No. 22, 2031 (1966).

    Google Scholar 

  229. Ya. A. Levin, K. N. Platonova, and V. A. Kuchin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1475 (1964).

    Google Scholar 

  230. R. P. Bokalders and A. Ya. Liepmno, Khim. Geterotsikl. Soedin., No. 3, 423 (1973).

    Google Scholar 

  231. R. G. W. Spickett and S. H. B. Wright, J. Chem. Soc., C, No. 6, 498 (1967).

    Google Scholar 

  232. R. W. J. Morrison and W. R. Mallory, J. Org. Chem., 43, 4844 (1978).

    Google Scholar 

  233. S. Nishigaki, M. Ychiba, J. Sato, K. Senga, M. Nogushi, and T. Yoneda, Heterocycles, No. 1, 11 (1978).

    Google Scholar 

  234. K. Senga, J. Sato, Y. Kanamori, M. Ychiba, S. Nichigaki, M. Noguchi, and F. Yoneda, J. Heterocycl. Chem., 15, 781 (1978).

    Google Scholar 

  235. F. L. Noce, E. Bellasio, A. Vigelani, and E. Testa, Ann. Chim. (Rome), 62, 647 (1972).

    Google Scholar 

  236. C. J. Temple, C. L. Kussner, and J. A. Montgomery, J. Org. Chem., 34, 3161 (1969).

    Google Scholar 

  237. C. J. Temple, C. L. Kussner, and J. A. Montgomery, J. Heterocycl. Chem., 10, 889 (1973).

    Google Scholar 

  238. D. J. Brown and T. Sugimoto, Aust. J. Chem., 14, 633 (1971).

    Google Scholar 

  239. M. Ychiba, S. Nishigaki, and K. Senga, Heterocycles, 6, 1921 (1977).

    Google Scholar 

  240. K. Senga, M. Ychiba, Y. Kanamori, and S. Nishigaki, Heterocycles, 7, 29 (1978).

    Google Scholar 

  241. G. Blankenhor and W. Pfleiderer, Chem. Ber., 105, 3334 (1972).

    Google Scholar 

  242. T. Yoneda, T. Nagamatsu, and K. Shinomura, J. Chem. Soc., Perkin Trans. I, No. 7, 713 (1976).

    Google Scholar 

  243. E. C. Taylor and F. Sowinsky, J. Org. Chem., 40, 2329 (1975).

    Google Scholar 

  244. E. C. Taylor and F. Sowinsky, J. Am. Chem. Soc., 91, 2143 (1975).

    Google Scholar 

  245. E. C. Taylor and F. Sowinsky, J. Org. Chem., 40, 2321 (1975).

    Google Scholar 

  246. C. Temple and J. A. Montgomery, J. Org. Chem., 28, 3038 (1963).

    Google Scholar 

  247. K. Senga, Y. Kanamori, and S. Nishigaki, Heterocycles, 6, 693 (1977).

    Google Scholar 

  248. T. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 23, 2001 (1975).

    Google Scholar 

  249. K. Senga, M. Ychiba, and S. Nishigaki, Tetrahedron Lett., No. 14, 1129 (1976).

    Google Scholar 

  250. K. Senga, M. Ychiba, and S. Nishigaki, J. Org. Chem., 43, 1677 (1978).

    Google Scholar 

  251. A. V. Ivashchenko, B. E. Zaitsev, S. V. Krikunova, and R. V. Poponova, Khim. Geterotsikl. Soedin., No. 12, 1682 (1980).

    Google Scholar 

  252. V. M. Dziomko, V. N. Avilina, and A. V. Ivashchenko, Koord. Khim., 6, 328 (1980).

    Google Scholar 

  253. V. M. Dziomko, A. V. Ivashchenko, O. N. Garicheva, L. V. Shmelev, and Yu. S. Ryabokobylko, Summaries of Papers Presented at the 1st All-Union Conference on Macroheterocycles and Their Open-Chain Analogs [in Russian], Odessa (in press).

  254. A. V. Ivashchenko, O. N. Garicheva, L. V. Shmelev, and Yu. S. Ryabokobylko, Khim. Geterotsikl. Soedin., No. 8, 1114 (1980).

    Google Scholar 

  255. A. V. Ivashchenko, O. N. Garicheva, L. V. Shmelev, Yu. S. Ryabokobylko, and G. M. Adamova, Khim. Geterotsikl. Soedin., No. 12, 1678 (1980).

    Google Scholar 

  256. A. V. Ivashchenko, O. N. Garicheva, L. V. Shmelev, Yu. S. Ryabokobylko, and G. M. Adamova, Khim. Geterotsikl. Soedin., No. 12, 1673 (1980).

    Google Scholar 

  257. V. M. Dziomko, A. V. Ivashchenko, O. N. Garicheva, L. V. Shmelev, Yu. S. Ryabokobylko, and G. M. Adamova, Khim. Geterotsikl. Soedin., No. 7, 963 (1981).

    Google Scholar 

  258. A. V. Ivashchenko, A. P. Bogdanov, A. I. Vasil'ev, O. N. Garicheva, E. S. Zaitseva, and I. I. Olikov, Koordinats. Khim., 7, 1084 (1981).

    Google Scholar 

  259. A. V. Ivashchenko, A. I. Vasil'ev, O. N. Garicheva, and E. S. Zaitseva, Koord. Khim., 8, 1236 (1981).

    Google Scholar 

  260. O. N. Garicheva, Author's Abstract of Candidate's Dissertation, Moscow (1981).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 579–600, May, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ivashchenko, A.V., Garicheva, O.N. Advances in the chemistry of hydrazinopyrimidines (review). Chem Heterocycl Compd 18, 429–448 (1982). https://doi.org/10.1007/BF00526073

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00526073

Keywords

Navigation