1,3,4-Thiadiazines: Methods of synthesis and reactivity (review) / Usol'tseva S.V., Andronnikova G.P., Mokrushin V.S. // Chemistry of Heterocyclic Compounds. - 1991. - V. 27, l. 4. - P. 343-354.

ISSN:
00093122
Type:
Review
Abstract:
The synthetic methods for 1,3,4-thiadiazines and their intramolecular rearrangement reactions are reviewed. © 1991 Plenum Publishing Corporation.
Author keywords:
Index keywords:
нет данных
DOI:
10.1007/BF00480827
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Affiliations S. M. Kirov Ural Polytechnical Institute, Sverdlovsk, Russian Federation
References Beyer, H., (1969) Z. Chem., 9, p. 361; Beyer, H., (1970) Q. Reports on Sulfur Chem., 5, p. 177; Bulka, E., Pfeiffer, W.D., Zur Entschwefelungstendenz von 2-Phenyl- und 2-Benzyl-1,3,4-thiadiazinen (1976) J. Prakt. Chem., 318, p. 971; Sandström, J., (1960) Ark. Kemi, 15, p. 195; Holmberg, B., (1955) Ark. Kemi, 9, p. 65; Sandström, J., (1954) Ark Kemi, 7, p. 249; Tadashi, S., Masaki, O., (1957) Yakugaku Zasshi, 77, p. 771; Methes, R.A., SOME MERCAPTOTHIADIAZINES AND THEIR INTERMEDIATE COMPOUNDS (1952) The Journal of Organic Chemistry, 17, p. 877; Sandström, J., (1955) Ark. Kemi, 9, p. 127; Dewey, G.H., Atutz, E.D., (1964) Rec. Trav. Chim., 83, p. 1047; Saikawa, J., Takano, S., (1971) C. A., 75, p. 5965; Beyer, H., Bulka, E., Beckhaus, F.W., Über die Synthese von 2-Methylmercapto-1.3.4-thiodiazinen und deren Umlagerung in Pyrazolderivate (1959) Chemische Berichte, 92, p. 2593; I. Ya. Postovskii, A. D. Sinegibskaya, A. P. Novikova, and L. P. Sidorova, in: Abstracts of Proceedings, 14th Scientific Meeting on the Chemistry and Technology of Organic Sulfur Compounds and Sulfur Oils, Riga (1976), p. 207; Sandström, J., The Reaction between Thiohydrazines and Ethyl Benzoylchloroacetate. Part I. Formation of Ethyl 5-Phenylpyrazole-4-carboxylates. (1962) Acta Chemica Scandinavica, 16, p. 2395; Sandström, J., (1955) Ark. Kemi, 8, p. 523; Bose, P.K., (1926) Q. J. Indian Chem. Soc., 3, p. 148; Brown, D., Hargreaves, R.B., McLoughlin, B.J., Mills, S.D., (1984) C. A., 100. , 22,672; Hargreaves, R.B., McLoughlin, B.J., Mills, S.D., (1984) C. A., 100, p. 6561; Brown, D., Hargreaves, R.B., McLoughlin, B.J., Mills, S.D., (1985) C. A., 102. , 149,291; Ao, H., Obata, M., Inui, I., (1986) C A., 105. , 97,488; Jonas, R., Piulats, J., Lues, I., Klockow, M., (1989) C. A., 110. , 192,866; Beyer, H., Lassig, W., Bulka, E., Über Thiazole, XX. Mitteil.): Die wahre Konstitution des in der Literatur beschriebenen, 2-Amino-5-methyl-1.3.4-thiodiazins (1954) Chemische Berichte, 87, p. 1385; Beyer, H., Lassig, W., Bulka, E., Behrens, D., Über Thiazole, XXI. Mitteil.): Die Synthese von alkylsubstituierten 2-Amino-1.3.4-thiodiazinen und deren Umlagerung in 3-Amino-thiazolon-(2)-imide (1954) Chemische Berichte, 87, p. 1392; Busby, R.E., Dominey, T.W., (1980) J. Chem. Soc., Perkin Trans. 2, 6, p. 890; Avramavici, S., (1955) Analele Stünt. Univ. “Al. I. Cuza,”, 1, p. 315; Beyer, H., Wolter, C., Über Thiazole, XXIX. Mitteil.: Über die Kondensationsprodukte von Thiosemicarbazid mit α- Chloracetessigester und eine neuartige Ringverengung des 2-Amino-5- methyl-6-carbäthoxy −1.3.4-thiodiazins zum 3-Methyl-4- carbäthoxy-5-amino-pyrazol (1956) Chemische Berichte, 89, p. 1652; Doyle, W.C., (1975) C. A., 82. , 171,094; Doyle, W.D., (1975) C. A., 82. , 112,114; Thiblaut, T.D., (1984) C. A., 101. , 23,510; Hildegard, J., Seifert, K., Johne, S., Bulka, E., (1978) Pharmazie, 33, p. 259; Campaigne, E., Selby, T.P., (1978) J. Heterocycl. Chem., 15, p. 401; Campaigne, E., Selby, T.P., (1981) C. A., 95. , 25,150; Walter, H.A., (1951) C. A., 45, p. 2714; Bose, P.K., (1921) Q. J. Indian Chem. Soc., 1, p. 51; Jones, W.D., Miller, F.P., (1982) C. A., 97. , 192,467; Jones, W.D., Miller, F.P., (1981) C. A., 95. , 81,033; Postovskii, Novikova, A.P., Chechulina, L.A., Sidorova, L.P., (1976) Khim. Geterotsikl. Soedin., 8, p. 1051; Ito, M., (1967) Yakugaku Zasshi, 87, p. 539; Zenno, H., Sugihara, A., Ito, M., (1967) C. A., 67. , 54,173; Djudjic, R., Trkovnik, M., Kitan, D., (1985) Org. Prep. Proc. Intern., 17, p. 206; Hadacek, J., Slotova-Trnkova, J., (1960) Pharmazie, 15, p. 226; Hadacek, J., Slotova-Trnkova, J., (1960) Spisy Prirod. Fak. Univ. Brne, 22, p. 39; Yoshida, N., Tanaka, K., Iizuka, Y., Wachi, K., Nishimura, T., Yasuda, H., (1975) C. A., 82. , 57,744; Jones, W.D., Miller, F.P., (1981) C. A., 95. , 115,618; Miller, F.P., Jones, W.D., (1981) C. A., 95. , 62,276; Jones, W.D., Miller, F.P., (1982) C. A., 96. , 181,397; Netherlands Appl. NL 8,006,206; C. A., 97, 216,243 (1982); Beyer, H., Lassig, W., Schultz, U., Über Thiazole, XXII. Mitteil.): Über das 2-Hydrazino-5-methyl-1.3.4-thiodiazin und dessen Umlagerung in das 3-Amino-4-methyl-thiazolon-(2)-hydrazon (1954) Chemische Berichte, 87, p. 1401; Kida, S., Ishikawa, H., Kawashima, Y., Tanaka, T., Matsuda, K., (1987) C. A., 106. , 215,514; Bose, P.K., (1925) Q. J. Indian Chem. Soc., 2, p. 95; Pfeiffer, W.D., Dilk, E., Bulka, E., (1977) Z. Chem., 17, p. 218; Bose, P.K., Nandi, B.K., (1930) J. Indian Chem. Soc., 7, p. 733; Bulka, E., Pfeiffer, W.D., Troeltsch, C., Dilk, E., Gaertner, H., Daniel, D., (1978) Coll., 43, p. 1227; Beyer, H., Honenck, H., Reichelt, L., (1970) Ann., 741, p. 45; Pfeiffer, W.D., Bulka, E., (1986) C. A., 104. , 68,891; Thorwart, W., Gebert, U., Scheleyerbach, R., Bartleu, R., (1988) C. A., 109. , 170,466; Tadashi, S., Masaki, O., (1954) Yakugaku Zasshi, 74, p. 821; Talger, E., El-Hewehi, Z., Synthese von in 5-Stellung mono- und disubstituierten 2-Mercapto-4-phenyl-?2-1,3,4-thiadiazolinen und 2,3-Dimercaptochinoxalin (1962) J. Prakt. Chem., 18, p. 255; L. P. Sidorova, A. P. Novikova, and I. Ya. Postovskii, Nucleophilic Reactions of Carbonyl Compounds, Abstracts of Proceedings, 2nd Conference of Schools of Higher Education, Saratov (1982), p. 129; Bose, P.K., (1926) Q. J. Indian Chem. Soc., 3, p. 197; Giammanco, L., (1964) Atti Accad. Sci., Lett. Arti Palermo, 23, p. 129; Pfeiffer, W.D., Dilk, E., Bulka, E., (1977) Z. Chem., 17, p. 173; Bose, P.K., Rav-Chaudhury, D.C., (1927) Q. J. Indian Chem. Soc., 4, p. 257; Pfeiffer, W.D., Bulka, E., Fermum, R., (1984) C. A., 101. , 191,974; Pfeiffer, W.D., Bilk, E., Bulka, E., (1984) C. A., 101, p. 7216; Petersen, U., Heitzer, H., (1974) C. A., 81. , 13,564; Petersen, U., Heitzer, H., Metzger, K.G., (1974) C. A., 81. , 25,700; Matsubara, Y., Yoshihara, M., Nakanura, T., Yamada, Maeshima, T., (1983) Phosp. Sulf., 16, p. 89; Matsubara, Y., Nakamura, T., Yoshihara, M., Maeshima, T., (1983) Kinki Daigaku Rikogakubu Kenkyu Hokoku, 18, p. 91; G. P. Andronnikova, S. L. Nikolaeva, S. V. Usol'tseva, and V. I. Shishkina, Advances in the Chemistry of Azines, Abstracts of Proceedings, 2nd All-Union Conference, Sverdlovsk (1985), p. 187; S. V. Usol'tseva, G. P. Andronnikova, S. L. Nikolaeva, and V. A. Shevyrin, Nucleophilic Reactions of Carbonyl Compounds, Abstracts of Proceedings, 3rd Conference of Schools of Higher Education, Saratov (1985), p. 69; P. Chabrier and E. Cattelain, Bull. Soc. Chim. France, 48 (1950); Holmberg, B., (1947) Ark. Kemi, Mineral. Geol., 25 A, p. 18; Sandström, J., (1952) Ark. Kemi, 4, p. 297; Sandström, J., (1955) Ark. Kemi, 8, p. 487; Soliman, R., Gabr, M., Abouzeit-Har, M., Sharabi, E.M., (1981) J. Pharm. Sci., 70, p. 94; Bose, P.K., Nandi, B.K., (1930) Q. J. Indian Chem. Soc., 7, p. 961; Winthrop, S., Gavin, G., 2-BENZHYDRYLIMINO-4-THIAZOLIDONES AND RELATED COMPOUNDS (1958) Canadian Journal of Chemistry, 36, p. 879; Klosa, J., (1954) Arch. Pharm., 287, p. 12; Edwards, L.H., (1982) C. A., 97. , 144,885; L. H. Edwards and J. D. Cleveland, European Patent No. 42,246; Bulka, E., Mittag, P., Berg, G., Beyer, H., (1962) Rev. Chem. Akad. PPR, 7, p. 725; Hampel, W., Kapp, M., Proksch, G., (1970) Z. Chem., 10, p. 142; Hampel, W., (1969) Z. Chem., 9, p. 61; Epshtein, S.P., Orlova, T.I., Rusakov, A.F., Tashchi, V.P., Putsykin, (1987) Khim. Geterotsikl. Soedin., 4, p. 554; Beyer, J., Thielemann, C., Thong, P.D., (1979) J. Prakt. Chem., 321, p. 959; Neugebauer, F.A., Fischer, H., (1965) Chem. Ber., 107, p. 717; Bulka, E., Ronde, H.G., Beyer, H., Über Thiazole, XLIII. Zur Kondensation substituierter Thiosemicarbazide mit α-Chlor-acetessigester (1965) Chemische Berichte, 98, p. 259; Beyer, H., Bulka, E., (1962) Z. Chem., 2, p. 321; Beyer, H., Wolter, G., Lemke, H., Über die Pyrazolbildung aus α-Chlor-acetessigester und Thiocarbohydrazid (1956) Chemische Berichte, 89, p. 2550; Beyer, H., Henseke, G., Bulka, E., Drews, H., Muller, E., Über Thiazole, XXXVIII. Synthesen neuer Sulfonamide in der Thiazolreihe (1959) Chemische Berichte, 92, p. 1105; Beyer, H., Bulka, E., (1956) Chem. Ber., 87, p. 223; Beyer, H., Ruhling, G., Über Thiazole, XXVI. Mitteil.: Die Synthese von 3-substituierten Thiazolon-(2)-imiden aus α-Rhodanketonen (1956) Chemische Berichte, 89, p. 107; Gregory, J.T., (1959) C. A., 53. , 11,419; Zachinaev, Petrov, M.L., Frolkov, A.N., Chistokletov, V.N., Petrov, A.A., (1980) Zh. Org. Khim., 16, p. 938; M. L. Petrov, V. N. Chistokletov, and A. A. Petrov, USSR Patent No. 537,999; Byull. Izobret., No. 45, 92 (1976); Petrov, M.L., Bobylev, V.V., Chistokletov, V.N., Petrov, A.A., (1981) Zh. Org. Khim., 17, p. 1100; Mohareb, R.M., Habashi, A., Hafez, E.A., Sherif, S.M., (1987) Arch. Pharm., 320, p. 776; Trepanier, D.L., Krieger, P.E., Mennear, J.H., Eble, J.H., (1967) J. Med. Chem., 10, p. 1085; Trepanier, D.L., Krieger, P.E., (1969) C. A., 70. , 106,577; Tadashi, S., Masaki, O., (1955) Yakugaku Zasshi, 75, p. 1535; Baydar, A.E., Boyd, G.V., Lindley, P.F., (1981) J. Chem. Soc., Chem. Commun., 19. , 10,030; Trepanier, D.L., Reifschneider, W., Shumaker, W., Tharpl, D.S., (1965) J. Org. Chem., 30, p. 2228; Trepanier, D.L., (1968) C. A., 68. , 29,729; Schultze, W., Letsch, G., Fritzsche, H., (1967) J. Prakt. Chem., 36, p. 128; Kristinsson, H., Winkler, T., Mollenkopf, M., Ringtransformationen von 3-substituiertem 5-Trifluormethyl-1,3,4-thiadiazol-2(3H)-on mit Nucleophilen (1983) Helvetica Chimica Acta, 66, p. 2714; Hirai, K., Ishiba, T., (1971) J. Chem. Soc. D, 20, p. 1318; Hirai, K., Ishiba, T., (1978) Chem. Pharm. Bull., 26, p. 3017; Evans, D.M., Taylor, D.R., Myers, M., (1984) J. Chem. Soc., Chem. Commun., 21, p. 1444; Setz, G., Mohr, R., Overheu, W., Allmann, R., Nagel, M., Donorsubstituierte Thiocarbonylverbindungen als Heterodienophile bei [4 + 2]-Cycloadditionen mit inversem Elektronenbedarf (1984) Angewandte Chemie, 96, p. 885; S. V. Usol'tseva, N. V. Volkova, G. P. Andronnikova, T. G. Koksharova, L. N. Dianova, S. L. Nikolaeva, V. A. Shevyrin, and A. L. Suetin, Nitrogen-Containing Heterocycles, Abstracts of Proceedings, 4th All-Union Conference, Novosibirsk (1987), p. 214; Pfeiffer, W.D., Bulka, E., (1976) Z. Chem., 16, p. 80; Pfeiffer, W.D., Dilk, E., Bulka, E., (1978) Z. Chem., 18, p. 65; Yoshida, N., Eachi, K., Tanaka, K., Iizuka, Y., (1975) C. A., 82. , 170,912; Yoshida, N., Mijazawa, H., Tanaka, K., Iizuka, Y., (1976) C. A., 85. , 46,637; Schmidt, R.R., Huth, H., (1975) Tetrahedron Lett., 1, p. 33; Pfeiffer, W.D., Geisler, K., Rossberg, H., Bulka, E., (1982) Z. Chem., 22, p. 137; Pfeiffer, W.D., Dilk, E., Bulka, E., (1977) Synthesis, 3, p. 196; Pfeiffer, W.D., Bulka, E., (1977) Synthesis, 7, p. 485; Pfeiffer, W.D., Rossberg, H., Bulka, E., (1986) C. A., 105. , 60,599; Pfeiffer, W.D., Bulka, E., (1985) C. A., 102. , 62,228; Pfeiffer, W.D., Bulka, E., Mietchen, R., (1987) Z. Chem., 27, p. 296; Pfeiffer, W.D., Mietchen, R., Bulka, E., (1988) C. A., 109. , 93,001; Pfeiffer, W.D., Bulka, E., (1986) C. A., 105. , 226,554; Japanese Patent No. 6,253,976; C. A., 107, 115,607 (1987); Dizon, J., Robinson, D.H., (1988) C. A., 108. , 37,839; R. B. Hargreaves and B. J. McLoughlin, European Patent No. 86301; Meyer, K.H., Schuetz, S., Stoepel, K., Kroneberg, H.G., (1968) C. A., 68. , 105,467; Brown, D., Dowell, R., Hargreaves, R.B., Main, B.G., (1982) C. A., 97. , 144,886; Cooper, F.B., Gross, P., Lewis, M., Chemotherapeutic Evaluation of Some N1- and N4-Heterocyclic Derivatives of Sulfanilamide (1941) Experimental Biology and Medicine, 47, p. 508; Takamizawa, A., Sato, H., (1970) C. A., 72. , 79,112; Takamizawa, A., Sato, H., (1970) C. A., 72. , 55,523; Takamizawa, A., Sato, H., (1970) C. A., 72. , 43,738; Usui, Y., (1969) Yakugaki Zasshi, 89, p. 689; Ruelfenacht, K., (1973) Helv. Chim. Acta, 56, p. 2186; Dovlatyan, V.V., Gevorkyan, R.A., (1976) Arm. Khim. Zh., 31, p. 851; Edwards, L., (1979) C. A., 91. , 20,550; Cleveland, J.D., Edwards, L., (1979) C. A., 91. , 108,013; L. V. Kholevinskaya, L. N. Emel'yanova, L. P. Sidorova, and A. V. Yuminov, USSR Inventor's Certificate No. 1,189,862; Byull. Isobret., No. 41, 103 (1985); Minagawa, G., Akutsu, M., Goto, M., (1976) C. A., 84. , 180,229; Roosens, L.P., (1961) C. A., 56, p. 8217
Correspondence Address Usol'tseva, S.V.; S. M. Kirov Ural Polytechnical Institute, Sverdlovsk, Russian Federation
Publisher Kluwer Academic Publishers-Plenum Publishers
CODEN CHCCA
Language of Original Document English
Abbreviated Source Title Chem Heterocycl Compd
Source Scopus