Abstract
This article is a critical survey of the literature on methods of synthesis, chemical properties, conversions, and applications of 1,3,4-thiadiazines and their hetaryl derivatives.
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Literature Cited
H. Beyer, Z. Chem., 9, 361 (1969).
S. Radl, Janssen Chim. Acta, 5, 3 (1987).
E. Bulka, W. D. Pfeiffer, C. Tröltsch, E. Dilk, H. Gartner, and D. Daniel, Collect. Czech. Chem. Commun., 43, 1227 (1978).
H. Johne, K. Seifert, S. Johne, and E. Bulka, Pharmazie, 33, 259 (1978).
S. F. Kahlilova and I. A. Poplavskaya, Izv. Akad. Nauk KazSSR, Ser. Khim., No. 1, 56 (1984).
E. Campaigne and T. P. Selby, J. Heterocycl. Chem., 15, 401 (1978).
I. Ya. Postovskii, A. P. Novikova, L. A. Chechulina, and L. P. Sidorova, Khim. Geterotsikl. Soedin., No. 8, 1051 (1976).
A. P. Novikova, N. M. Perova, L. G. Egerova, and E. I. Bragina, Khim. Geterotsikl. Soedin., No. 6, 843 (1991).
A. P. Novikova, N. M. Perova, L. G. Egerova, and E. I. Bragina, Carbonyl Compounds in the Synthesis of Heterocycles [in Russian], Izd. SGU, Saratov (1989), Vol. 2, p. 106.
W. C. Doyle, US Patent 3,862,183; Chem. Abstr., 82, 171094 (1975).
Sh. Kida, K. Ishikawa, J. Kawashima, T. Tanaka, and K. Masuda, Japanese Patent 61,250,072; Chem. Abstr., 106, 215514 (1987).
N. Yoshida, K. Tanaka, Y. Iizuka, K. Wachi, T. Nishimura, and H. Takuzo, Japanese Patent 7,488,889; Chem. Abstr., 82, 57744 (1975).
W. Schulze, G. Letsch, and H. Fritsche, J. Prakt. Chem., 36, 138 (1967).
W. D. Pfeiffer, E. Dilk, and E. Bulka, Z. Chem., 17, 173 (1977).
W. D. Pfeiffer, E. Bulka, and F. Reinhard, German Patent 209,196; Chem. Abstr., 101, 191974 (1984).
W. D. Pfeiffer, E. Dilk, and E. Bulka, German Patent 204,092; Chem. Abstr., 101, 7216 (1984).
Y. Tomita, Sh. Kabashima, T. Okawara, T. Yamasaki, and M. Furukawa, J. Heterocycl. Chem., 27, 707 (1990).
D. Kallias, C. I. Stassinopoulou, and P. Catsoulacos, J. Heterocycl. Chem., 17, 1045 (1980).
W. D. Pfeiffer and E. Bulka, Z. Chem., 29, 288 (1989).
W. Hampel, Z. Chem., 9, 61 (1969).
W. Hampel, M. Kapp, and G. Proksch, Z. Chem., 10, 142 (1970).
R. M. Mochareb, A. Habashi, A. A. Hafez, and S. M. Sherif, Arch. Pharm., 320, 776 (1987).
T. V. Sarawathi, V.R. Rao, V. R. Srinivasan, and M. Ramaih, Indian J. Chem., 10, 1151 (1972).
W. Veerabhadraiah, V. R. Rao, T. V. Rao, and Padmanabha, J. Indian Chem. Soc., 67, 81 (1990).
B. Holmberg, Arkiv Kemi, 9, 65 (1956).
J. Sandstrom, Arkiv Kemi, 7, 249 (1954).
J. Sandstrom, Arkiv Kemi, 9, 127 (1955).
T. Sato and M. Ohta, Yakugaki Zasshi, 77, 771 (1957); Chem. Abstr., 51, 17941 (1957).
J. Sandstrom, Acta Chem. Scand., 16, 2395 (1962).
J. Beger, C. Thielemann, and P. D. Thong, J. Prakt. Chem., 321, 959 (1979).
E. Taeger and Z. El-Hewehi, J. Prakt. Chem., 18, 255 (1962).
R. Hüll, J. Chem. Soc., 2959 (1952).
V. V. Dovlatyan and R. A. Gevorkyan, Arm. Khim. Zh., 31, 851 (1978).
L. P. Sidorova, A. P. Novikova, and I. Ya. Postovskii, Nucleophilic Reacts of Carbonyl Compounds [in Russian], Saratov (1982), p. 129.
D. M. Evans, D. R. Taylor, and M. Myer, Chem. Commun., No. 21, 1444 (1984).
P. Molina, A. Arques, I. Cartagena, and J. M. Olmos, Synthesis, No. 7, 518 (1989).
B. F. Bonini, C. Maccagnani, G. Mazzanti, L. Thijs, C. E. Veenstra, and B. Zwanenberg, J. Chem. Soc., Perkin 1, No. 10, 1218 (1978).
A. Takamizawa and H. Sato, Japanese Patent 6,928,103; Chem. Abstr., 72, 43738 (1970).
A. Takamizawa and H. Sato, Japanese Patent 6,927,896; Chem. Abstr., 72, 55523 (1970).
A. Takamizawa and H. Sato, Japanese Patent 6,928,102; Chem. Abstr., 72, 79112 (1970).
A. Takamizawa and H. Sato, Chem. Pharm. Bull., 18, 1201 (1970).
H. Kristinsson, T. Winkler, and M. Mollenkopf, Helv. Chim. Acta, 66, 2714 (1983).
Y. Kamitori, M. Hojo, R. Masuda, Y. Kawamura, and T. Numai, Synthesis, No. 6, 491 (1990).
K. Hirai and T. Ishiba, Chem., 1318 (1971).
K. Hirai and T. Ishiba, Chem. Pharm. Bull., 26, 3017 (1978).
G. Seitz, R. Mohr, W. Overheu, and R. Allmann, Angew. Chem., 96, 885 (1984).
Ya. V. Zachinyaev, M. L. Petrov, A. N. Frolkov, V. N. chistokletov, and A. A. Petrov, Zh. Org. Khim., 16, 938 (1980).
Y. V. Zachinyaev, A. E. Bobrov, and A. I. Gynak, Rev. Roum. Chem., 34, 901 (1989).
S. Hoff and E. Zwanenburg, Rec. Trav. Chim., 92, 929 (1973).
M. L. Petrov, V. A. Bobylev, V. N. Chistokletov, and A. A. Petrov, Zh. Org. Khm., 17, 1100 (1981).
M. L. Petrov, V. N. Chistokletov, and A. A. Petrov, USSR Inventor's Certificate No. 537,999; Byull. Izobret., No. 45, 92 (1976).
V. A. Bobylev, M. L. Petrov, V. N. Chistokletov, and A. A. Petrov, Zh. Org. Khim., 17, 2289 (1981).
S. M. Shevchenko and A. A. Potekhin, Khim. Geterotsikl. Soedin., No. 11, 1569 (1978).
S. M. Shevchenko and A. A. Potekhin, USSR Inventor's Certificate 749,840; Byull. Izobret., No. 27, 102 (1980).
A. A. Potekhin and S. M. Shevchenko, Khim. Geterotsikl. Soedin., No. 10, 1355 (1981).
S. M. Shevchenko and A. A. Potekhin, Khim. Geterotsikl. Soedin., No. 12, 1637 (1979).
A. R. Katritzky, R. C. Patel, and D. M. Read, Tetrahedron Lett., No. 43, 3803 (1977).
U. Ptersen and H. heitzer, Justus Liebigs Ann. Chem., No. 5–6, 944 (1973).
U. Petersen and H. Heitzer, German Patent 2,251,683; Chem. Abstr., 81, 13564 (1974).
U. Petersen, H. Heitzer, and K. G. Metzger, German Patent 2,251,684; Chem. Abstr., 81, 25700 (1974).
E. Bulka, P. Mittag, G. Berg, and H. Beyer, Rev. Chim., 7, 725 (1962).
V. I. Pleshnev and N. M. Turkevich, Metody Poluch. Khim. Reakt. Prep. (Moscow), No. 23, 67 (1971).
A. A. Kuzhelyuk, N. M. Turkevich, A. V. Babak, and L. T. Emchik, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 16, 1516 (1973).
R. Soliman, M. Gabr, M. S. Abouzeit-Har, and F. M. Sharabi, J. Pharm. Sci., 70, 94 (1981).
L. H. Edwards, Canadian Patent 1,121,349; Chem. Abstr., 97, 144885 (1982).
T. Okawara, R. Kato, T. Yamasaki, N. Yasuda, and M. Furukawa, Heterocycles, 24, 885 (1986).
D. Brown, R. I. Hargreaves, and B. G. Main, European Patent 52,442; Chem. Abstr., 97, 144886 (1982).
B. Holmberg, Arkiv Kemi, 9, 47 (1956).
Y. Matsubara, M. Yoshihara, T. Nakanura, Sh. Yamada, and T. Maeshima, Phosphorus Sulfur, 16, 89 (1983).
Y. Matsubara, T. Kakamura, and M. Yoshihara, Rikogakubu Kenkyu Hokoku, No. 18, 91 (1983).
Y. Matsubara, Sh. Yamada, M. Yoshihara, and T. Maeshima, Phosphorus Sulfur, 22, 41 (1985).
Y. Matsubara, S. Yamada, M. Yoshihara, and T. Maeshima, Chem. Pharm. Bull., 32, 1590 (1984).
Y. Matsubara, S. yamada, M. Yoshihara, and T. Maeshima, Nippon Kagaku Kaishi, No. 7, 1312 (1987).
G. Ege, Ph. Arnold, G. Jooss, and R. Noronha, Justus Liebigs Ann. Chem., No. 5, 791 (1977).
R. B. Hargreaves, B. J. McLoughlin, and S. D. Mills, European Patent 851,227; Chem. Abstr., 110, 192866 (1989).
R. Jonas, J. Piulats, I. Lues, M. Klockow, European Patent 294,647; Chem. Abstr., 110, 192866 (1989).
A. E. Baydar, G. Boyd, and P. F. Lindley, Chem. Commun., No. 19, 1003 (1981).
W. D. Pfeiffer, E. Dilk, and E. Bulka, Z. Chem., 17, 15 (1977).
Sh. Kida, T. Tanaka, and K. Masuda, Japanese Patent 61,260,085; Chem. Abstr., 106, 138475 (1987).
Y. Usui, Yakugaku Zasshi, 89, 689 (1969).
E. Bulka and W. D. Pfeiffer, Z. Chem., 15, 482 (1975).
I. V. Smolanka, T. A. Krasnitskaya, and M. M. Tsitsika, Ukr. Khim. Zh., 38, 587 (1972).
N. Yoshida, K. Wachi, K. Tanaka, and Y. Iizuka, Japanese Patent 74,110,696; Chem. Abstr., 82, 171096 (1975).
N. Yoshida, K. Wachi, and K. Tanaka, Japanese Patent 74,110,697; Chem. Abstr., 82, 171095 (1975).
G. Fenech and M. Basile, Ann. Chim., 53, 848 (1963).
G. Fenech and M. Basile, Gazz. Chim. Ital., 96, 897 (1966).
G. Scherowsky, Tetrahedron Lett., 52, 4985 (1971).
M. Ito, Yakugaku Zasshi, 87, 539 (1967).
R. Djudjik, M. Trkovnik, and D. Kitan, Org. Prep. Proc. Int., 17, 206 (1985).
W. D. Pfeiffer and E. Bulka, German Patent 235,640; Chem. Abstr., 105, 226554 (1986).
N. Yoshida, K. Wachi, and K. Tanaka, Japanese Patent 74,100,080; Chem. Abstr., 82, 170912 (1975).
E. Bulka and W. D. Pfeiffer, J. Prakt. Chem., 318, 971 (1976).
W. D. Pfeiffer and E. Bulka, Z. Chem., 16, 80 (1976).
N. Yoshida, H. Miyazawa, K. Tanaka, and Y. Iizuka, Japanese Patent 75,130,760; Chem. Abstr., 85, 46637 (1976).
W. D. Pfeiffer, E. Bulka, and R. Miethchen, Z. Chem., 27, 296 (1987).
W. D. Pfeiffer, R. Miethchin, and E. Bulka, German Patent 253,030; Chem. Abstr., 109, 93001 (1988).
H. Beyer, H. Honeck, and Z. Reichelt, Justus Liebigs Ann. Chem., 741, 45 (1970).
H. Ohachi and N. Mizukura, Japanese Patent 901077; Chem. Abstr., 113, 115317 (1990).
J. Hadacek and J. Slotova-Trnkova, Pharmazie, 15, 226 (1960).
R. E. Busby and T. W. Dominey, J. Chem. Soc., Perkin Trans. 2, No. 6, 890 (1980).
E. E. Campaigne and T. Selby, US Patent 4,254,259; Chem. Abstr., 95, 25150 (1981).
W. D. Pfeiffer, I. Buhrow, and E. Bulka, Wiss. Z. Ernst-Moritz-Arndt-Univ. Greifsw., Med. Riehe, 37, 38 (1988).
W. D. Pfeiffer, E. Dilk, and E. Bulka, Synthesis, No. 3, 196 (1977).
I. Brawford-Bryce, Chem. Abstr., 112, 118039 (1990).
W. D. Pfeiffer, E. Dilk, and E. Bulka, Z. Chem., 18, 65 (1978).
R. R. Schmidt and H. Huth, Tetrahedron Lett., No. 1, 33 (1975).
L. P. Sidorova, L. G. Egorova, and A. P. Novikova, in: Summaries of Papers from 16th Conference on the Chemistry and Technology of Organic Sulfur Compounds and Sour Crude Oils, Riga (1984), p. 264.
L. P. Sidorova and A. R. Sabitova, New Developments in the Chemistry of Azines [in Russian], Sverdlovsk (1985), p. 196.
W. D. Pfeiffer and E. Bulka, Synthesis, No. 7, 495 (1977).
W. D. Pfeiffer, E. Dilk, and E. Bulka, Z. Chem., 17, 218 (1977).
Y. Isomura, Sh. Sakamoto, N. Ito, H. Homma, T. Abe, and K. Kubo, Chem. Pharm. Bull., 32, 152 (1984).
V. G. Baklykov, V. N. Charushin, O. N. Chupakhin, and V. N. Drozd, Khim. Geterotsikl. Soedin., No. 4, 557 (1987).
T. D. Thibault, US Patent 4,436,549; Chem. Abstr., 101, 23510 (1984).
W. D. Pfeiffer, K. Geisler, H. Rossberg, and E. Bulka, Z. Chem., 22, 137 (1982).
W. D. Pfeiffer and E. Bulka, German Patent 211,343; Chem. Abstr., 102, 62228 (1985).
W. D. Pfeiffer, H. Rossberg, and E. Bulka, German Patent 228,248; Chem. Abstr., 105, 60599 (1986).
D. B. Denney and M. J. Boskin, J. Am. Chem. Soc., 82, 4736 (1960).
J. D. Cleveland and L. H. Edwards, US Patent 4,158,732; Chem. Abstr., 91, 108013 (1979).
Y. Matsubara, T. Nakamura, M. Yoshihara, and T. Maeshima, Chem. Pharm. Bull., 33, 3009 (1985).
H. Zenno, A. Sugihara, and M. Ito, Japanese Patent 678,033; Chem. Abstr., 67, 54173 (1967).
I. Saikava and Sh. Takano, Japanese Patent 7,041,593; Chem. Abstr., 75, 5965 (1971).
Z. El-Gendy, R. M. Abdel-Rahmab, and M. S. Abdel-Malik, Indian J. Chem. B, 288, 479 (1989).
F. B. Cooper, P. Gross, and M. Lewis, Proc. Soc. Exp. Biol. Med., 47, 508 (1941).
D. L. Trepanier, US Patent 3,290,303; Chem. Abstr., 68, 29729 (1968).
A. M. El-Naggar, A. M. A. El-Salam, I. M. Ismail, B. M. Haroun, and A. M. Gommaa, Indian J. Chem. B, 198, 1088 (1980).
A. B. Tomchin, I. A. Zhmykhova, M. M. Ponomareva, L. V. Pastushenkov, and E. G. Gromova, Khim.-farm. Zh., 20, 1051 (1986).
W. Thorwart, U. Gebert, R. Schleyerbach, and R. Bartlett, German Patent 3,702,756; Chem. Abstr., 109, 170466 (1988).
W. Thorwart, U. Gebert, R. Schleyerbach, and R. Bartlett, German Patent 3,702,757; Chem. Abstr., 110, 8223 (1989).
W. J. Coates, H. D. Prain, M. L. Reeves, and B. H. Warrington, J. Med. Chem., 33, 1735 (1990).
R. C. Brown, J. Dixon, and D. H. Robinson, German Patent 253,426; Chem. Abstr., 109, 129065 (1988).
S. K. Kotovskaya, L. A. Tyurina, E. Yu. Chernova, G. A. Mokrushina, O. N. Chupakhin, A. P. Novikova, and V. I. Il'enko, Khim.-farm. Zh., 23, 310 (1989).
A. P. Novikova, L. P. Sidorova, L. A. Chechulina, I. Ya. Postovskii, I. P. Tregubenko, and é. A. Tarakhtii, Problems in Modem Radiation Pharmacology [in Russian], Moscow (1980), p. 31.
D. L. Trepanier, P. E. Krieger, J. H. Mennear, and J. N. Ebie, J. Med. Chem., 10, 1085 (1967).
D. L. Trepanier and P. E. Krieger, US Patent 3,428,631; Chem. Abstr., 70, 106577 (1969).
F. P. Miller and W. D. Jones, Belgium Patent 884,990; Chem. Abstr., 95, 62276 (1981).
W. D. Jones and F. P. Miller, German Patent 30,313,703; Chem. Abstr., 95, 81033 (1981).
M. Martin, G. Nadler, and R. Zimmermann, European Patent 303,418; Chem. Abstr., 111, 97293 (1989).
W. D. Jones and F. P. Miller, Belium Patent 884,991; Chem. Abstr., 95, 115618 (1981).
W. D. Jones and F. P. Miller, US Patent 4,309,426; Chem. Abstr., 96, 181316 (1982).
W. Jones and F. Miller, German Patent 3,042,295; Ref. Zh. Khim., 130119 (1983).
M. G. Collis, J. R. Keddic, and W. Rouse, Br. J. Pharmacol., 97, 409 (1989).
W. D. Pfeiffer and E. Bulka, German Patent 220,311; Chem. Abstr., 104, 68891 (1986).
K. H. Meyer, S. Schuetz, K. Stoepel, and H. G. Kroneberg, US Patent 3,328,387; Chem. Abstr., 68, 105467 (1968).
Japanese Patent 58,131,973; Chem. Abstr., 100, 6567 (1984).
D. Brown, R. B. Hargreaves, B. J. McLoughlin, and S. D. Mills, European Patent 80,296; Chem. Abstr., 100, 22672 (1984).
D. Brown, R. B. Hargreaves, B. J. McLoughlin, and S. D. Mills, US Patent 4,489,074; Chem. Abstr., 102, 149291 (1985).
Japanese Patent 8,753,976; Chem. Abstr., 107, 115608 (1987).
European Patent 180,159; Chem. Abstr., 105, 97488 (1986).
W. J. Coates, European Patent 220,44; Chem. Abstr., 108, 112503 (1988).
H. Morioka, M. Takezava, H. Shibai, T. Kato, N. Ysuda, T. Furukawa, and T. Okawara, Japanese Patent 60,239,320; Chem. Abstr., 104, 207251 (1986).
K. Ruefenacht, Helv. Chim. Acta, 56, 2186 (1973).
W. C. Doyle, US Patent 3,779,736; Chem. Abstr., 80, 129266 (1974).
W. C. Doyle, US Patent 3,854,924; Chem. Abstr., 82, 112114 (1975).
L. H. Edwards, US Patent 3,144,335; Chem. Abstr., 91, 20550 (1979).
H. A. Walter, US Patent 2,534,087; Chem. Abstr., 45, 2714 (1951).
H. A. Walter, US Patent 2,536,521; Chem. Abstr., 45, 2718 (1951).
J. T. Gregory, US Patent 2,871,237; Chem. Abstr., 53, 11419 (1959).
J. T. Gregory, US Patent 2,871,238; Chem. Abstr., 53, 11419 (1959).
G. Minagawa, M. Akutsu, and M. Goto, Japanese Patent 7,537,651; Chem. Abstr., 84, 180229 (1976).
K. Ishizuka, Japanese Patent 7,405,439; Chem. Abstr., 82, 59824 (1975).
A. J. Elliott, US Patent 4,025,510; Chem. Abstr., 87, 153420 (1977).
T. Fujino and Sh. Fueki, Japanese Patent 7,137,646; Chem. Abstr., 77, 147067 (1972).
Belium Patent 571,916; Chem. Abstr., 56, 8217 (1962).
L. W. Tregilus and A. A. Rasch, US Patent 3,017,270; Chem. Abstr., 57, 1791 (1962).
French Patent 1,410,426; Chem. Abstr., 64, 2913 (1966).
N. V. Gevaert-Agfa, Netherlands Patent 6,615,207; Chem. Abstr., 67, 69444 (1967).
P. D. van Pee and J. F. Willems, French Patent 1,496,599; Chem. Abstr., 69, 320027 (1968).
L. M. De Haes, H. K. Gevers, and J. J. Vanheertum, Belgium Patent 716,778; Chem. Abstr., 71, 66074 (1969).
A. Rasch, French Patent 2,001, 160; Chem. Abstr., 73, 72077 (1970).
Y. Kawashima, H. Ishikawa, Sh. Kida, T. Tanaka, and K. Masuda, Japanese Patent 61,260,085; Chem. Abstr., 106, 138475 (1987).
Y. Kaneko, Japanese Patent 63,256,951; Chem. Abstr., 111, 105647 (1989).
L. V. Kholevinskaya, L. N. Emel'yanova, L. P. Sidorova, and A. V. Yuminov, USSR Inventor's Certificate 1,189,862; Byull. Izobret., No. 41, 103 (1985).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1443–1457, November, 1991.
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Novikova, A.P., Perova, N.M. & Chupakhin, O.N. Synthesis and properties of functional derivatives of 1,3,4-thiadiazines and condensed systems based on these compounds (review). Chem Heterocycl Compd 27, 1159–1172 (1991). https://doi.org/10.1007/BF00471738
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DOI: https://doi.org/10.1007/BF00471738