Abstract
The results of investigations on the structure, methods of synthesis, and chemical properties of the aminofurazans are generalized.
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Literature cited
A. F. Holleman, Recl. Trav. Chim., 6, 60 (1887).
A. F. Holleman, Chem. Ber., 21, 2835 (1888).
G. Ponzio and C. Cerrina, Gaz. Chim. Ital., 58, 26 (1928).
R. C. Bertelson, K. D. Glanz, and D. B. McQuain, J. Heterocycl. Chem., 6, 317 (1969).
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 498,137.
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 498,857.
C. Lehmann, E. Renk, and A. Gagneux, Czechoslovakian Patent No. 140,464.
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 498,135.
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 498,854.
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 498,134.
C. Lehmann, E. Renk, and A. Gagneux, GFR Patent No. 1,903,569; Chem. Abstr., 71, No. 128, 725 (1969).
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 498,136.
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 498,856.
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 498,855.
C. Lehmann, E. Renk, and A. Gagneux, South African Patent, No. 6,800,799; Chem. Abstr., 70, No. 57, 855 (1969).
C. Lehmann and E. Renk, Swiss Patent, No. 479,605.
C. Lehmann and E. Renk, Swiss Patent, No. 479,606.
C. Lehmann and E. Renk, US Patent, No. 3,711,609.
C. Lehmann, E. Renk, and A. Gagneux, South African Patent No. 6,800,778; Chem. Abstr., 71, 3387 (1969).
C. Lehmann and E. Renk, Swiss Patent, No. 480,352.
C. Lehmann and E. Renk, Swiss Patent, No. 481,126.
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 502,365.
A. Fundaro, Boll. Soc. It. Biol. Sper., 50, 1650 (1974).
R. Calvino and A. Fundaro, Farmaco, Ed. Sci., 32, 789 (1977).
C. Lehmann, E. Renk, and A. Gagneux, Swiss Patent, No. 508,650.
C. Lehmann, E. Renk, and A. Gagneux, Czechoslovakian Patent, No. 140,460.
C. Lehmann and E. Renk, Swiss Patent, No. 478,825.
J. Boyer, in: Heterocyclic Compounds, R. C. Elderfield (ed.), Wiley, New York, Vol. 7 (1961), p. 462.
L. C. Behr, in: Five- and Six-Membered Compounds with Nitrogen and Oxygen, R. H. Wiley (ed.), Interscience, New York (1962), p. 283.
K. L. Stuart, Heterocycles, 3, 651 (1975).
T. Ichikawa, T. Kato, and T. Takenishi, Japanese Patent No. 20,710; Chem. Abstr., 64, 2101 (1966).
C. Grundmann, V. Mini, J. M. Dean, and H.-D. Frommeld, Ann. Chem., 687, 191 (1965).
S. Cusmano, Gazz. Chim. Ital., 81, 106 (1951).
A. R. Gagneux and R. Meier, Helv. Chim. Acta, 53, 1883 (1970).
M. D. Coburn, J. Heterocycl. Chem., 5, 83 (1968).
A. P. Komin, R. W. Street, and M. Carmack, J. Org. Chem., 40, 2749 (1975).
I. V. Vigalok and A. V. Ostrovskaya, in: The Chemistry and Technology of Organometallic Compounds and Polymers [in Russian], Kazan', No. 7 (1978), p. 48.
T. Ichikawa, T. Kato, and T. Takenishi, J. Heterocycl. Chem., 2, 253 (1965).
E. Durio and S. Dugone, Gazz. Chim. Ital., 66, 139 (1936).
F. Angelico and S. Cusmano, Gazz. Chim. Ital., 66, 3 (1936).
M. Iwao and T. Kuraishi, J. Heterocycl. Chem., 16, 689 (1979).
G. Westphal and R. Schmidt, J. Prakt. Chem., 315, 791 (1973).
T. E. Ivanova, S. N. Vergizov, S. F. Mel'nikova, and I. V. Tselinskii, USSR Inventors Certificate, No. 2,629,465; Byull. Izobret., No. 6, 75 (1980).
A. Russanov, Chem. Ber., 24, 3497 (1891).
G. Ponzio, Gazz. Chim. Ital., 62, 854 (1932).
E. Durio and A. Sburlati, Gazz. Chim. Ital., 62, 1035 (1932).
W. Zinkeisen, Chem. Ber., 22, 2946 (1889).
G. Longo, Gazz. Chim. Ital., 62, 873 (1932).
G. Ponzio and G. Bertini, Gazz. Chim. Ital., 61, 51 (1931).
G. Longo, Gazz. Chim. Ital., 61, 575 (1931).
H. Wieland and H. Hess, Chem. Ber., 42, 1346 (1909).
I. Paolini, Gazz. Chim. Ital., 58, 196 (1928).
I. Paolini and A. Castiglioni, Gazz. Chim. Ital., 59, 723 (1929).
G. Ponzio, Gazz. Chim. Ital., 60, 886 (1930).
G. Ponzio and L. Avogadro, Gazz. Chim. Ital., 53, 318 (1923).
G. Ponzio, Gazz. Chim. Ital., 61, 704 (1931).
A. Vianello, Gazz. Chim. Ital., 58, 326 (1928).
G. Ponzio and E. Durio, Gazz. Chim. Ital., 60, 436 (1930).
R. A. Olofson and J. S. Michelman, J. Org. Chem., 30, 1854 (1965).
G. Ponzio, Gazz. Chim. Ital., 61, 561 (1931).
G. Longo and G. Randone, Gazz. Chim. Ital., 66, 145 (1936).
G. Ponzio and L. Avogadro, Gazz. Chim. Ital., 53, 305 (1923).
G. Longo, Gazz. Chim. Ital., 62, 139 (1932).
P. Gramantieri, Gazz. Chim. Ital., 65, 102 (1935).
G. Ponzio, Gazz. Chim. Ital., 61, 138 (1931).
G. Ponzio and G. Ruggeru, Gazz. Chim. Ital., 53, 297 (1923).
S. Gusmano and M. Ruccia, Gazz. Chim. Ital., 88, 463 (1958).
S. Gusmano and M. Ruccia, Gazz. Chim. Ital., 86, 187 (1956).
A. F. Holleman, Recl. Trav. Chim., 11, 258 (1892).
J. Boeseken and D. P. Ross van Lennep, Recl. Trav. Chim., 31, 196 (1912).
A. F. Holleman, Recl. Trav. Chim., 10, 211 (1891).
J. Boeseken, Recl. Trav. Chim., 16, 297 (1897).
J. Boeseken, Recl. Trav. Chim., 29, 275 (1910).
H. Wieland and E. Gmelin, Ann. Chem., 375, 297 (1910).
A. V. Eremeev, V. G. Andrianov, and I. P. Piskunova, Khim. Geterotsikl. Soedin., No. 5, 616 (1978).
C. Ulpiani, Gazz. Chim. Ital., II, 35, 7 (1905).
C. Ulpiani, Gazz. Chim. Ital., I, 42, 375 (1912).
H. Wieland, Z. Kitasato, and S. Utzino, Ann. Chem., 478, 43 (1930).
C. Grundmann, G. W. Nickel, and R. K. Bansal, Ann. Chem., No. 6, 1029 (1975).
G. Ponzio, Gazz. Chim. Ital., 66, 114 (1936).
G. Ponzio, Gazz. Chim. Ital., 66, 119 (1936).
G. Ponzio, Gazz. Chim. Ital., 66, 127 (1936).
A. Gasco, V. Mortarini, G. Rua, and A. Serafino, J. Heterocycl. Chem., 10, 587 (1973).
J. E. Oliver, S. C. Chang, R. T. Brown, J. B. Stokes, and A. B. Borkovec, J. Med. Chem., 15, 315 (1972).
J. M. Tedder and D. J. Woodcock, J. Chem. Res. (s), No. 9, 356 (1978).
A. Gasco, G. Rua, E. Menziani, V. Mortarini, and A. Fundaro, Farmaco, Ed. Sci., 26, 241 (1971).
E. C. Taylor, G. P. Beardsley, and Y. Maki, J. Org. Chem., 36, 3211 (1971).
P. Fernandes-Resa, P. Goya Laza, C. Ochoade Ocariz, and M. S. Schueter, Spanish Patent, No. 497,899; Chem. Abstr., 97, No. 23, 790 (1982).
P. C. Guha and M. N. Chakladar, Proceedings of the 15th Indian Science Congress (1928), p. 157; Chem. Abstr., 25, 2999 (1931).
D. Viterbo and A. Serafino, Acta Crystallogr., B34, 3444 (1978).
M. A. Shokhen, V. G. Andrianov, and A. V. Eremeev, Khim. Geterotsikl. Soedin., No. 10, 1355 (1979).
I. V. Tselinskii, S. F. Mel'nikova, and S. N. Vergizov, Khim. Geterotsikl. Soedin., No. 3, 321 (1981).
R. Kraft, P. Helklein, G. Etzold, and H. Zopfl., J. Org. Mass. Spectrom., 11, 304 (1976).
E. Borello, A. Zecchina, and E. Guglielminotti, Gazz. Chim. Ital., 95, 1465 (1965).
E. Borello, A. Zecchina, and E. Guglielminotti, Gazz. Chim. Ital., 96, 532 (1966).
M. Milone and E. Borello, Gazz. Chim. Ital., 81, 386 (1951).
M. Milone and S. Allavena, Gazz. Chim. Ital., 61, 75 (1931).
V. V. Zverev, I. Sh. Saifullin, and G. P. Sharnin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 313 (1978).
V. G. Prokudin, G. M. Nazin, and G. B. Manelis, Dokl. Akad. Nauk SSSR, 255, 917 (1980).
I. V. Tselinskii, S. F. Mel'nikova, S. N. Vergizov, and G. M. Frolova, Khim. Geterotsikl. Soedin., No. 1, 35 (1981).
I. V. Tselinskii, S. F. Mel'nikova, and S. N. Vergizov, Zh. Org. Khim., 17, 1123 (1981).
G. Ponzio, Gazz. Chem. Ital., 62, 415 (1932).
G. Ponzio, Gazz. Chim. Ital., 62, 860 (1932).
D. Viterbo, R. Calvino, and A. Serafino, J. Chem. Soc., Perkin. Trans. II, No. 7, 1096 (1980).
R. Calvino, V. Mortarini, and A. Gasco, Eur. J. Med. Chem.-Chim. Ter., 15, 485 (1980).
R. Calvino, A. Gasco, A. Serafino, and D. Viterbo, J. Chem. Soc., Perkin Trans. II, No. 9, 1240 (1981).
M. N. Makhova, I. V. Ovchinnikov, B. N. Khasanov, and L. I. Khmel'nitskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 646 (1982).
G. D. Solodyuk, M. D. Bold'rev, B. V. Gidaspov, and V. D. Nikolaev, Zh. Org. Khim., 17, 861 (1981).
A. Matsumoto, M. Yoshida, and O. Simamura, Bull. Chem. Soc. Jpn., 47, 1493 (1974).
T. Takenisu, T. Kato, and T. Itikawa, Japanese Patent, No. 15,577 (66).
A. V. Eremeev, V. G. Andrianov, and I. P. Poshunova, Khim. Geterotsikl. Soedin., No. 3, 319 (1979).
A. Gasco, G. Rua, E. Menziani, and V. Mortarini, Farmaco, Ed. Sci., 26, 233 (1971).
A. Gasco, G. Rua, E. Menziani, G. M. Nano, and G. Tappi, J. Heterocycl. Chem., 6, 769 (1969).
G. Tappi and C. Migliardi, Arch. Sci. Biol., 27, 170 (1941).
G. Tappi and C. Migliardi, Arch. Sci. Biol., 28, 472 (1942).
G. Tappi, Recl. Trav. Chim., 62, 207 (1943).
R. O. Roblin and G. W. Anderson, US Patent, No. 2,367,057; Chem. Abstr., 39, 2383 (1945).
G. W. Anderson, H. E. Faith, H. W. Marson, P. S. Winnek, and R. O. Roblin, J. Am. Chem. Soc., 64, 2902 (1942).
M. Ruccia, N. Vivona, G. Cusmano, and G. Macaluso, J. Chem. Soc., Perkin Trans. I, No. 6, 589 (1977).
N. Vivona, G. Cusmano, and G. Macaluso, J. Chem. Soc., Perkin Trans. I, No. 14, 1616 (1977).
P. H. Bell and R. O. Roblin, J. Am. Chem. Soc., 64, 2905 (1942).
A. V. Ostrovskaya, I. V. Vigalok, and N. V. Svetlakov, USSR Inventors' Certificate, No. 771,117; Byull. Izobret., No. 38, pp142 (1980).
N. Sato and J. Adachi, J. Org. Chem., 43, 341 (1978).
A. Gasco, G. Rua, E. Menziani, G. M. Nano, and G. Tappi, J. Heterocycl. Chem., 7, 131 (1970).
A. V. Eremeev, V. G. Andrianov, and I. P. Piskunova, Khim. Geterotsikl. Soedin., No. 5, 613 (1978).
A. V. Eremeev, V. G. Andrianov, and I. P. Piskunova, Khim. Geterotsikl. Soedin., No. 9, 1196 (1978).
I. P. Bachkovskii, A. P. Mikhailovskii, and V. A. Chuiguk, Ukr. Khim. Zh., 46, 637 (1980).
A. J. Boulton, A. R. Katritzky, and A. M. Hamid, J. Chem. Soc., No. 20, 2005 (1967).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1155–1170, September, 1984.
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Andrianov, V.G., Eremeev, A.V. Aminofurazans (review). Chem Heterocycl Compd 20, 937–951 (1984). https://doi.org/10.1007/BF00506384
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DOI: https://doi.org/10.1007/BF00506384