Abstract
The literature data on methods for the synthesis of annelated 1,2,4-triazole systems on the basis of α-hydrazino-substituted heterocycles and their hydrazones are correlated, and their chemical properties and biological activity are examined briefly.
Similar content being viewed by others
References
G. A. Reynolds and J. A. Van Allan, Zh. Org. Khim., 24, 1478 (1959).
H. Reimlinger, J. J. M. Vandewalle, and W. R. F. Lingier, Chem. Ber., 103, 1960 (1970).
K. T. Potts and H. R. Burton, J. Org. Chem., 31, 251 (1966).
W. Marckwald and E. Meyer, Ber., 33, 1885 (1900).
F. S. Babichev and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., No. 2, 147 (1977).
R. N. Butler, F. L. Scott, and T. A. F. O'Mahony, Chem. Rev., 73, 93 (1973).
B. Stanovnik and M. Tisler, Croat. Chem. Acta, 49, 135 (1977).
R. N. Butler and S. M. Johnston, J. Chem. Soc., Chem. Commun., No. 8, 376 (1981).
R. N. Butler and S. M. Johnston, J. Chem. Soc., Perkin I, No. 9, 2109 (1984).
S. Naqui and V. R. Srinivasan, Indian J. Chem., 3, 162 (1965).
R. N. Butler, P. O'Sillivan, and F. L. Scott, J. Chem. Soc., Perkin I, No. 12, 1519 (1972).
M. S. Gibson, Tetrahedron, 19, 1587 (1963).
R. N. Butler and F. L. Scott, Chem. Ind., No. 38, 1216 (1970).
J. D. Bower and F. P. Doyle, J. Chem. Soc., No. 2, 727 (1957).
H. Gehlen and F. Lemme, Ann., 703, 116 (1967).
F. L. Scott and R. N. Butler, J. Chem. Soc., C, No. 13, 1202 (1966).
C. F. H. Allen, G. A. Reynolds, J. F. Tinker, and L. A. Williams, J. Org. Chem., 25, 361 (1960).
R. N. Butler, P. O'Sillivan, and F. L. Scott, J. Chem. Soc., C, No. 12, 2265 (1971).
A. Pollak, B. Stanovnik, and M. Tisler, J. Heterocycl. Chem., 5, 513 (1968).
J. Kobe, B. Stanovnik, and M. Tisler, Tetrahedron, 26, 3357 (1970).
T. Tsujikawa and M. Tatsuta, Heterocycles, 6, 423 (1977).
S. Crljenak, I. Tabakovic, D. Jeremic, and I. Gaon, Acta Chem. Scand., Ser. B, 37, 527 (1983).
S. Tagami, M. Sawaki, and D. Shihoh, Chem. Pharm. Bull., 17, 1983 (1969).
G. S. Sidhu, S. Naqui, and D. S. Iyengar, J. Heterocycl. Chem., 3, 158 (1966).
W. A. F. Gladstone, J. Chem. Soc., Chem. Commun., No. 4, 179 (1969).
W. A. F. Gladstone, J. B. Aylward, and R. O. C. Norman, J. Chem. Soc., C, No. 18, 2587 (1969).
T. A. F. O'Mahony, R. N. Butler, and F. L. Scott, J. Chem. Soc., Perkin II, No. 10, 1319 (1972).
F. L. Scott and T. A. F. O'Mahony, Tetrahedron Lett., No. 21, 1841 (1970).
D. J. Brown, G. W. Grigg, Y. Iwai, K. N. McAndrew, T. Nagamatsu, and R. Van Heeswyck, Austral. J. Chem., 32, 2713 (1979).
H. Reimlinger, R. W. Shanahan, and J. J. M. Vandewalle, US Patent No. 3,823,238; Chem. Abstr., 82, 26,146 (1975).
P. L. Anderson, W. J. Houlihan, and R. E. Manning, US Patent No. 3,708,484; Chem. Abstr., 78, 84,454 (1973).
M. Nakanishi, T. Tahara, K. Araki, and M. Shiroki, German Offen. No. 2,229,845; Chem. Abstr., 78, 84,416 (1973).
R. N. Butler, Chem. Ind., No. 14, 437 (1968).
K. T. Potts, Chem. Rev., 61, 87 (1961).
J. M. Burgess and M. S. Gibson, J. Chem. Soc., No. 4, 1500 (1964).
R. N. Butler and F. L. Scott, J. Chem. Soc., C, No. 3, 239 (1967).
D. C. Iffland, L. Salisbury, and W. R. Schaefer, J. Am. Chem. Soc., 83, 747 (1961).
B. T. Gillis and M. L. La Montagne, J. Org. Chem., 33, 762 (1968).
B. T. Gillis and M. L. La Montagne, J. Org. Chem., 33, 1294 (1968).
M. J. Harrison, R. O. C. Norman, and W. A. F. Gladstone, J. Chem. Soc., C, No. 8, 735 (1967).
R. N. Butler, Chem. Ind., No. 12, 499 (1976).
J. B. Aylward, Quart. Rev., 25, 407 (1971).
T. Sasaki and T. Yoshioka, Bull. Chem. Soc. Jpn., 43, 1254 (1970).
R. Kuhn and W. Munzing, Chem. Ber., 85, 29 (1952).
J. March, Organic Chemistry [Russian translation], Vol. 1, Mir, Moscow (1987), p. 280.
J. Warkentin, Synthesis, No. 6, 279 (1970).
C. F. Boehringer, British Patent No. 1,131,590; Chem. Abstr., 70, 28,926 (1969).
A. Pollak and M. Tisler, Tetrahedron, 22, 2073 (1966).
K. Shirakawa, J. Pharm. Soc. Jpn., 80, 956 (1960); Chem. Abstr., 54, 24,761 (1960).
R. G. W. Spickett and S. H. B. Wright, J. Chem. Soc., C, No. 6, 498 (1967).
R. G. W. Spickett and S. H. B. Wright, British Patent No. 1,070,243; Chem. Abstr., 67, 100,157 (1967).
M. Jelenc, J. Kobe, B. Stanovnik, and M. Tisler, Monatsh. Chem., 97, 1713 (1966).
L. Daunis, R. Jacquier, and P. Viallefont, Bull. Soc. Chim. France, No. 7, 2492 (1969).
K. T. Potts and C. Hirsch, J. Org. Chem., 33, 143 (1968).
R. N. Butler and F. L. Scott, J. Org. Chem., 31, 1319 (1966).
R. N. Butler and F. L. Scott, J. Chem. Soc., C, No. 14, 1711 (1968).
R. N. Butler, T. M. Lambe, and F. L. Scott, J. Chem. Soc., Perkin I, No. 3, 269 (1972).
H. Berger, K. Stach, and W. Voemel, South African Patent No. 6,706,255; Chem. Abstr., 70, 57,869 (1969).
B. Stanovnik and M. Tisler, Tetrahedron, 23, 387 (1967).
B. Stanovnik, M. Tisler, M. Ceglar, and V. Bah, J. Org. Chem., 35, 1138 (1970).
A. H. Beckett, R. G. W. Spickett, and S. H. B. Wright, Tetrahedron, 24, 2839 (1968).
L. A. Williams, J. Chem. Soc., No. 4, 1829 (1960).
C. F. H. Allen, H. R. Beilfuss, D. M. Burness, G. A. Reynolds, G. F. Tinker, and J. A. Van Allan, J. Org. Chem., 24, 787 (1959).
C. Temple, C. L. Kussner, and J. A. Montgomery, J. Org. Chem., 30, 3601 (1965).
A. Kovacic, B. Stanovnik, and M. Tisler, J. Heterocycl. Chem., 5, 351 (1968).
R. N. Butler and W. B. King, Chem. Ind., No. 14, 647 (1975).
S. Naqui and V. R. Srinivasan, J. Sci. Ind. Res., B21, 456 (1962).
F. L. Scott, R. N. Butler, and D. A. Cronin, Angew. Chem., 77, 963 (1965).
B. Stanovnik, A. Mozer, and M. Tisler, Rad Jugosl. Akad. Znan. Imjet., 425, 61 (1986); Chem. Abstr., 108, 221,652 (1988).
B. Stanovnik, A. Krbavcic, and M. Tisler, J. Org. Chem., 32, 1139 (1967).
F. L. Scott, J. K. O'Halloran, J. O'Driscoll, and A. F. Hegarty, J. Chem. Soc., Perkin I, No. 17, 2224 (1972).
F. L. Scott, D. A. Cronin, and J. K. O'Halloran, J. Chem. Soc., C, No. 16, 2769 (1971).
A. F. Hegarty, P. J. Moroney, A. Moynihan, and F. L. Scott, J. Chem. Soc., Perkin II, No. 2, 1892 (1972).
F. L. Scott, T. M. Lambe, and R. N. Butler, Tetrahedron Lett., No. 20, 1729 (1971).
F. L. Scott and J. K. O'Halloran, Tetrahedron Lett., No. 47, 4083 (1970).
F. L. Scott and D. A. Cronin, Tetrahedron Lett., No. 11, 715 (1963).
F. L. Scott and J. B. Aylward, Tetrahedron Lett., No. 13, 841 (1965).
A. F. Hegarty, P. Quain, T. A. F. O'Mahony, and F. L. Scott, J. Chem. Soc., Perkin II, No. 9, 997 (1974).
F. L. Scott and M. N. Holland, Proc. Chem. Soc., No. 3, 106 (1962).
T. Tsujikawa and M. Tatsuta, Chem. Pharm. Bull., 25, 3137 (1977).
I. Tabakovic, M. Trkovnik, and D. Galijas, J. Electroanal. Chem., 86, 241 (1978).
I. Tabakovic and S. Crljenak, Heterocycles, 16, 699 (1981).
W. D. Pfeiffer, E. Dilk, and E. Bulka, Z. Chem., 17, 15 (1977).
A. Haase and S. Biniecki, Acta Polon. Pharm., 18, 461 (1961).
K. Shirakawa, J. Pharm. Soc. Jpn., 80, 952 (1960); Chem. Abstr., 54, 24,761 (1960).
N. Takahayashi, J. Pharm. Soc. Jpn., 76, 1296 (1956); Chem. Abstr., 51, 6645 (1957).
K. Shirakawa, Japanese Patent No. 3326 ('59); Chem. Abstr., 54, 14,278 (1960).
J. A. Van Allan, US Patent No. 2,865,749; Chem. Abstr., 53, 21,309 (1959).
G. A. Reynolds, J. A. Van Allan, and J. F. Tinker, Chem. Abstr., 24, 633 (1971).
D. J. Brown and T. Sugimoto, Austral. J. Chem., 24, 633 (1971).
M. Japely, B. Stanovnik, and M. Tisler, Monatsh. Chem., 100, 671 (1969).
B. Camerino, G. Palamidessi, and R. Sciaky, Gazz. Chim. Ital., 90, 1821 (1960).
B. Camerino, G. Palamidessi, and R. Sciaky, Gazz. Chim. Ital., 90, 1830 (1960).
W. Marckwald and K. Rudzik, Ber., 36, 1111 (1903).
R. Graf, E. Lederer-Ponzer, V. Kopetz, R. Purkert, and P. Laszlo, J. Prakt. Chem., 138, 244 (1933); Chem. Abstr., 28, 769 (1934).
J. Druey and B. H. Ringier, Helv. Chim. Acta, 34, 195 (1951).
E. Birr and W. Walther, Chem. Ber., 86, 1401 (1953).
A. Dornow, H. Pietsch, and P. Marx, Chem. Ber., 97, 2647 (1964).
T. Kuraishi and R. N. Castle, J. Heterocycl. Chem., 1, 42 (1964).
B. Stanovnik and M. Tisler, Tetrahedron Lett., No. 22, 2403 (1966).
J. Daunis, M. Guerret-Rigail, and R. Jacquier, Bull. Soc. Chim. France, No. 8, 3043 (1971).
T. Kuraishi and R. N. Castle, J. Heterocycl. Chem., 3, 218 (1966).
K. Magarajan and R. K. Shah, Indian J. Chem., 12, 263 (1974).
H. Paul, G. Reichmann, and E. Mantey, Z. Chem., 8, 302 (1968).
B. A. Dreikorn and K. E. Kramer, German Offen. No. 2,239,892; Chem. Abstr., 78, 136,304 (1973).
J. B. Hester, German Offen. No. 2,220,612; Chem. Abstr., 78, 29,839 (1973).
J. B. Bicking, US Patent No. 2,917,511; Chem. Abstr., 54, 8854 (1960).
J. B. Bicking, US Patent No. 3,050,525; Chem. Abstr., 58, 1480 (1963).
V. G. Karp and V. A. Portnyagina, Khim.-farm. Zh., 4, 29 (1970).
J. B. Hester, German Offen. No. 2,244,571; Chem. Abstr., 78, 148,010 (1973).
C. Cristescu, Romanian Patent No. 56,269; Chem. Abstr., 82, 16,868 (1975).
T. Sasaki and K. Minamoto, Chem. Ber., 100, 3467 (1967).
T. Kauffmann, K. Vogt, S. Barck, and J. Schulz, Chem. Ber., 99, 2593 (1966).
K. T. Potts and S. Husain, J. Org. Chem., 36, 10 (1971).
I. Kumashiro, Nippon Kagaku Zasshi, 82, 1068 (1961); Chem. Abstr., 59, 621 (1963).
K. Shirakawa, J. Pharm. Soc. Jpn., 79, 899 (1959); Chem. Abstr., 54, 556 (1960).
K. Shirakawa, J. Pharm. Soc. Jpn., 79, 903 (1959); Chem. Abstr., 54, 556 (1960).
N. Takahayashi, J. Pharm. Soc. Jpn., 75, 1242 (1955); Chem. Abstr., 50, 8655 (1956).
J. Daunis, R. Jacquier, and P. Viallefont, Bull. Soc. Chim. France, No. 10, 3670 (1969).
D. Shiho and S. Tagami, J. Am. Chem. Soc., 82, 4044 (1960).
K. T. Potts and C. Lovelette, J. Org. Chem., 34, 3221 (1969).
D. S. Brown and T. Nagamatsu, Austral. J. Chem., 32, 1585 (1979).
D. Shiho, S. Tagami, N. Takahayashi, and R. Honda, J. Pharm. Soc. Jpn., 76, 804 (1956); Chem. Abstr., 51, 1196 (1957).
R. J. Deshpande and A. V. Rama Rao, Synthesis, No. 12, 863 (1974).
Gy. Hajos and A. Messmer, J. Heterocycl. Chem., 15, 463 (1978).
H. Reimlinger, Chem. Ber., 103, 3278 (1970).
C. F. H. Alien, H. R. Beilfuss, D. M. Burness, G. A. Reynolds, J. F. Tinker, and J. A. Van Allan, J. Org. Chem., 24, 793 (1959).
B. Jenko, B. Stanovnik, and M. Tisler, Synthesis, No. 12, 833 (1976).
K. Shirakawa, J. Pharm. Soc. Jpn., 79, 1482 (1959); Chem. Abstr., 54, 11,039 (1960).
K. Shirakawa, J. Pharm. Soc. Jpn., 78, 1395 (1958); Chem. Abstr., 53, 8150 (1959).
K. Shirakawa, J. Pharm. Soc. Jpn., 79, 1487 (1959); Chem. Abstr., 54, 11,039 (1960).
H. Reimlinger and M. A. Peiren, Chem. Abstr., 103, 3266 (1970).
H. Kano and Y. Makisumi, Chem. Pharm. Bull., 7, 907 (1959).
W. W. Paudler and L. S. Helmick, J. Heterocycl. Chem., 3, 269 (1966).
H. Reimlinger, R. Jacquier, and J. Daunis, Chem. Ber., 104, 2702 (1971).
D. J. Brown and T. Nagamatsu, Austral. J. Chem., 30, 2515 (1977).
F. D'Alo and A. Masserini, Ann. Chim. (Rome), 57, 366 (1967); Chem. Abstr., 67, 43,784 (1967).
V. A. Ershov and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., No. 6, 1134 (1968).
P. J. Nelson and K. T. Potts, J. Org. Chem., 27, 3243 (1962).
K. T. Potts and S. W. Schneller, J. Heterocycl. Chem., 5, 485 (1968).
D. J. Brown and K. Shinozuka, Austral. J. Chem., 34, 2635 (1981).
B. Stanovnik, M. Tisler, and R. Skufca, J. Org. Chem., 33, 2910 (1968).
D. J. Brown and K. Shinozuka, Austral. J. Chem., 34, 189 (1981).
Ch. J. Paget, German Offen. No. 2,250,077; Chem. Abstr., 79, 18,721 (1973).
H. Beyer, Z. Chem., 10, 399 (1970).
J. A. Van Allan, US Patent No. 2,891,862; Chem. Abstr., 54, 4224 (1960).
M. Kanaoka, Pharm. Bull., 5, 385 (1957); Chem. Abstr., 52, 5390 (1958).
C. F. H. Allen, H. R. Beilfuss, D. M. Burness, G. A. Reynolds, J. F. Tinker, and J. A. Van Allan, J. Org. Chem., 24, 779 (1959).
D. J. Brown and T. Nagamatsu, Austral. J. Chem., 31, 2505 (1978).
C. Temple, R. L. McKee, and J. A. Montgomery, J. Org. Chem., 28, 2257 (1963).
A. Krbavcic, B. Stanovnik, and M. Tisler, Croat. Chem. Acta, 40, 181 (1968).
N. Takahayashi, Pharm. Bull., 5, 229 (1957); Chem. Abstr., 52, 6359 (1958).
L. N. Yakhontov, N. N. Suvorov, E. V. Pronina, V. Ya. Kanterov, N. Ya. Podkhalyuzina, N. E. Starostenko, and V. N. Shkil'kova, Khim. Geterotsikl. Soedin., No. 8, 1146 (1972).
T. Sasaki, K. Minamoto, and S. Fukuda, Chem. Ber., 101, 2747 (1968).
J. B. Hester, A. D. Rudzik, and B. V. Kamdar, J. Med. Chem., 14, 1078 (1971).
H. Reimlinger, W. R. F. Lingier, and J. J. M. Vandewalle, Chem. Ber., 104, 639 (1971).
K. T. Potts and R. M. Huseby, J. Org. Chem., 31, 3528 (1966).
G. M. Badger, P. J. Nelson, and K. T. Potts, J. Org. Chem., 29, 2542 (1964).
R. Huisgen, H. J. Sturm, and M. Scidel, Chem. Ber., 94, 1555 (1961).
Farbenfabriken Bayer Akt.-Ges., British Patent No. 825,514; Chem. Abstr., 55, 7450 (1961).
H. Reimlinger, J. J. M. Vandewalle, G. S. D. King, W. R. F. Lingier, and R. Merenyi, Chem. Ber., 103, 1918 (1970).
K. T., Potts, J. Bhattacharyya, S. L. Smith, A. M. Ihrig, and C. A. Girard, J. Org. Chem., 37, 4410 (1972).
O. Dimroth, Arm., 364, 183 (1909).
K. Shirakawa, J. Pharm. Soc. Jpn., 80, 1550 (1960); Chem. Abstr., 55, 10,450 (1961).
K. T. Potts, E. G. Brugel, and W. C. Dunlap, Tetrahedron, 33, 1247 (1977).
K. T. Potts, W. C. Dunlap, and F. S. Apple, Tetrahedron, 33, 1263 (1977).
K. T. Potts, H. R. Burton, and S. K. Roy, J. Org. Chem., 31, 265 (1966).
T. P. Sycheva, I. D. Kiseleva, and M. N. Shukina, Khim. Geterotsikl. Soedin., No. 7, 916 (1970).
T. George, D. V. Mehta, R. Tahilramani, J. Dabid, and P. K. Talwalker, J. Med. Chem., 14, 335 (1971).
G. E. Hardtmann and F. G. Kathawala, German Offen. No. 2,261,095; Chem. Abstr., 79, 66,385 (1973).
G. W. Miller and F. L. Rose, British Patent No. 897,870; Chem. Abstr., 58, 10,211 (1963).
T. P. Sycheva, I. D. Kiseleva, T. N. Zykova, and M. N. Shchukina, Khim.-farm. Zh., 7, 12 (1973).
Roche Products Ltd., British Patent No. 711,756; Chem. Abstr., 49, 11,723 (1955).
H. Berger, R. Gall, H. Merdes, K. Stach, and W. Sauer, German Offen. No. 2,109,570; Chem. Abstr., 78, 84,431 (1973).
M. Likar, P. Schauer, M. Japelj, M. Globokar, M. Oklobdzija, A. Povse, and V. Sunjic, J. Med. Chem., 13, 159 (1970).
H. Berger, R. Gall, H. Merdes, K. Stach, W. Sauer, and W. Voemel, German Offen. No. 2,030,218; Chem. Abstr., 76, 72,536 (1972).
H. Berger, R. Gall, H. Merdes, K. Stach, W. Sauer, and W. Voemel, German Offen. No. 2,153,902; Chem. Abstr., 79, 42,534 (1973).
W. Von Bebenburg, German Offen. No. 2,416,608; Chem. Abstr., 82, 43,481 (1975).
D. L. Coffen and R. J. Fryer, US Patent No. 3,849,434; Chem. Abstr., 82, 73,044 (1975).
M. E. Goldberg, US Patent No. 3,746,714; Chem. Abstr., 79, 100,768 (1973).
S. Yusurugi, T. Fushimi, and A. Miyake, Japanese Patent No. 7,247,396; Chem. Abstr., 78, 111,329 (1973).
G. W. Miller and F. L. Rose, British Patent No. 898,408; Chem. Abstr., 57, 11,209 (1962).
D. J. Brown, W. C. Dunlap, G. W. Grigg, L. Danckwerts, and T. Nagamatsu, Austral. J. Chem., 31, 397 (1978).
H. Kano and Y. Makisumi, Chem. Pharm. Bull., 6, 583 (1958).
H. Kano, Y. Makisumi, S. Takahashi, and M. Ogata, Chem. Pharm. Bull., 7, 903 (1959).
Y. Makisumi, H. Kano, and S. Takahashi, Japanese Patent No. 9499 ('62); Chem. Abstr., 59, 5178 (1963).
Y. Makisumi, H. Kano, and S. Takahashi, Japanese Patent No. 9498 ('62); Chem. Abstr., 59, 5178 (1963).
H. Kano and T. Noguchi, Japanese Patent No. 7,126,500; Chem. Abstr., 75, 140,863 (1971).
H. Hoffmann and I. Hammann, German Offen. No. 1,942,015; Chem. Abstr., 74, 141,816 (1971).
Kodak Soc. Anon., Belgian Patent No. 559,022; Chem. Abstr., 54, 132 (1960).
E. B. Knott and L. A. Williams, US Patent No. 2,861,076; Chem. Abstr., 53, 9251 (1959).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1587–1613, December, 1993.
Rights and permissions
About this article
Cite this article
Gizatullina, É.M., Kartsev, V.G. Annelation of the 1,2,4-triazole ring on the basis of α-hydrazino-substituted heterocycles and their hydrazones (review). Chem Heterocycl Compd 29, 1369–1392 (1993). https://doi.org/10.1007/BF00531397
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00531397