Abstract
Literature data on methods for the synthesis of cyclic thioureas and their physicochemical properties and transformations are correlated.
Similar content being viewed by others
Literature cited
E. J. Lein and W. D. Kumler, J. Med. Chem., 11, 214 (1968).
M. H. Hussain and E. J. Lien, J. Med. Chem., 14, 138 (1971).
R. Tweit, US Patent No. 3025295; Ref. Zh. Khim., 23N157P (1963).
J. R. Geigy, A.-G. Geigy, West German Patent No. 1107215; Chem. Abstr., 56, 8573 (1962).
W. L. Matier, D. A. Owens, W. F. Comer, D. Deitchman, H. C. Ferguson, R. J. Seidehamel, and J. R. Young, J. Med. Chem., 16, 901 (1973).
J. B. Bream and C. W. Picard, US Patent No. 3822262; Izobr. Rubezhom, 15, Part 1, No. 13 (1974).
H. K. Hall and A. K. Schneider, J. Am. Chem. Soc., 80, 6409 (1958).
J. J. D'Amico and M. D. Dexter, US Patent No. 3728355; Chem. Abstr., 79, 20065 (1973).
A. Safaev, A. Kadyrov, Zh. G. Saidaliev, and G. Sh. Artukova, USSR Inventor's Certificate No. 503865; Ref. Zh. Khim., 10N171P (1977).
W. H. Hensley, D. C. Forgeson, and J. A. Lambrech, US Patent No. 3190887; Ref. Zh. Khim., 13N656 (1967).
S. I. Orlov, A. V. Tsyban', É. Sh. Khasan'yanova, V. P. Zvolinskii, V. S. Smolyakov, A. A. Savina, N. A. Bakulinko, and L. D. Stonov, USSR Inventor's Certificate No. 506362; Ref. Zh. Khim., 140438P (1979).
A. F. McKay and W. G. Hatton, J. Am. Chem. Soc., 78, 1618 (1956).
A. F. McKay and M. E. Kreling, Can. J. Chem., 35, 1438 (1957).
E. Z. Strack, Physiol. Chem., 180, 198 (1928).
V. P. Arya, V. Honkan, and S. J. Shenoy, Indian J. Chem., 14B, 773 (1976).
B. A. Kazansky (editor), Organic Syntheses [Russian translation], Vol. 4, Inostr. Lit., Moscow (1953), p. 574.
J. Kister, G. Assef, H. J. M. Dou, and J. Metzger, Tetrahedron, 32, 1395 (1976).
N. Kimpe, R. Verhe, L. Buyck, and N. Shamp, J. Org. Chem., 42, 3704 (1977).
F. B. Zienty, J. Am. Chem. Soc., 68, 1388 (1946).
G. D. Thorn, Can. J. Chem., 33, 1278 (1955).
R. A. Donia, J. A. Shotton, L. O. Bentz, and G. E. P. Smith, J. Org. Chem., 14, 946 (1949).
G. E. Hardtmann, L. Koletar, O. R. Pfister, J. H. Gogerty, and L. C. Iorio, J. Med. Chem., 18, 447 (1975).
G. Gramm and C. D. Barnikel, British Patent No. 1557020; Izobr. SSSR Rubezhom, 55, No. 12 (1980).
US Patent No. 2921073; Chem. Abstr., 72, 8660 (1960).
J. F. Willems, Chem. Fortschr., 4, 561 (1963).
H. Behringer and H. Meier, Ann. Chem., 607, 67 (1957).
A. V. Bogatskii, K. S. Luk'yanenko, and T. I. Kirichenko, Zh. Org. Khim., 16, 1301 (1980).
A. V. Bogatskii, (Bogatsky), N. G. Luk'yanenko (Lukyanenko), and T. I. Kirichenko, Tetrahedron Lett., 21, 313 (1980).
K. N. M. Prasad, Indian J. Chem., B, 17, 405 (1979).
R. Neidlein and W. D. Ober, Monatsh. Chem., 107, 1241 (1976).
B. Dietrich, T. M. Fyles, J. M. Lehn, L. G. Pease, and D. L. Fyles, Chem. Commun., No. 21, 934 (1978).
R. R. Wittekind, T. Capiris, J. Fahey, and J. Shavel, J. Org. Chem., 38, 1641 (1973).
R. L. Clark, A. A. Pessolano, Tsung-Ying Shen, D. P. Jacobus, and H. Jones, J. Med. Chem., 21, 965 (1978).
A. A. Popov, V. M. Zaichenko, G. A. Lysova, and F. A. Galil-Ogly, USSR Inventor's Certificate No. 476262; Ref. Zh. Khim., 8N177P (1977).
A. A. Popov and I. I. Rozhnyatovskii, USSR, Inventor's Certificate No. 403675; Ref. Zh. Khim., 20N243P (1974).
M. D. Hurwitz and R. W. Auten, US Patent No. 2613212; Chem. Abstr., 48, 2782 (1954).
A. A. Popov, G. A. Lysova, and F. A. Galil-Ogly, USSR Inventor's Certificate No. 434083; Ref. Zh. Khim., 110165P (1975).
R. A. Mathes and F. D. Stewart, US Patent No. 2491509; Chem. Abstr., 44, 5400 (1950).
H. Petersen, West German Patent No. 1670086; Ref. Zh. Khim., 22N217N (1976).
H. Petersen, West German Patent No. 1670129; Ref. Zh. Khim., 22N218P (1976).
E. Enders, V. Ebbinghausen, W. Gau, C. Wünsche, and W. Stendel, British Patent No. 1569490; Izobr. SSSR Rubezhom, 55, No. 5 (1981).
A. V. Bogatskii, K. S. Zakharov, N. G. Luk'yanenko, and T. I. Kirichenko, Zh. Org. Khim., 18, 1101 (1982).
P. J. Wheatley, Acta Crystallogr., 6, 369 (1953).
M. Mammi, F. D'Angeli, and S. Bezzi, J. Chem. Soc., No. 6, 1521 (1965).
S. Sato, T. Kinoshita, T. Hata, and C. Tamura, Acta Crystallogr., B, 32, 918 (1976).
H. W. Dias and M. R. Truter, Acta Crystallogr., 17, 937 (1964).
A. Pra, C. Bello, and M. Mammi, Ric. Sci., 37, 754 (1967).
M. Mammi, A. Pra, and C. Bello, Ric. Sci., 37, 766 (1967).
G. Piero and C. Bello, Acta Crystallogr., B, 27, 2035 (1971).
A. Pra, Acta Crystallogr., 22, 926 (1967).
Yu. G. Ganin, Yu. A. Simonov, N. G. Luk'yanenko, A. V. Bogatskii, T, I. Kirichenko, and M. M. Botoshanskii, Dokl. Akad. Nauk SSSR, 260, 95 (1981).
N. K. Dalley, in: Synthetic Multidentate Macrocyclic Compounds, edited by R. M. Izatt and J. J. Christensen, Academic Press, New York-San Francisco-London (1978), p. 207.
M. R. Truter, Acta Crystallogr., 22, 556 (1967).
W. D. Kumler and G. M. Fohlen, J. Am. Chem. Soc., 64, 1944 (1942).
H. G. Mautner and W. D. Kumler, J. Am. Chem. Soc., 78, 97 (1956).
C. M. Lee and W. D. Kumler, J. Org. Chem., 27, 2052 (1962).
E. J. Lien, J. T. Chou, and G. A. Guadauskas, Spectroscopy Lett., 5, 293 (1972).
G. Assef, D. Bouin-Roubaud, J. Kister, and J. Metzger, Compt. Rend., C, 283, 143 (1976).
G. Assef, D. Bouin-Roubaud, J. Kister, and J. Metzger, Compt. Rend., C, 282, 485 (1976).
D. Bouin-Roubaud, J. Kister, G. Assef, and J. Metzger, Compt. Rend., C, 286, 521 (1978).
V. C. Jyorhi, R. Arabinda, and C. C. Patel, Indian J. Phys., 51, 211 (1977).
R. Mecke, R. Mecke, and A. Lutringhaus, Z. Naturf., B, 105, 367 (1955).
R. Mecke and R. Mecke, Chem. Ber., 89, 343 (1956).
H. W. Thompson, D. N. Nicolson, and L. N. Short, Discuss. Faraday Soc., 9, 222 (1950).
M. H. Hussain and E. J. Lien, Spectroscopy Lett., 6, 97 (1973).
F. Cristiani, F. A. Devillanova, and G. Verani, J. Chem. Soc., Perkin Trans. II, No. 3, 324 (1977).
F. A. Devillanova and G. Verani, J. Chem. Soc., Perkin Trans. II, No. 12, 1529 (1977).
F. A. Devillanova and G. Verani, Aust. J. Chem., 31, 2609 (1978).
F. A. Devillanova, D. N. Sathyanarayana, and G. Verani, J. Heterocycl. Chem., 15, 945 (1978).
F. A. Devillanova and G. Verani, Aust. J. Chem., 33, 279 (1980).
S. O. Wandiga, L. S. Jankins, and G. R. Willey, J. Inorg. Nucl. Chem., 41, 941 (1979).
K. Dwarakanath and D. N. Sathyanarayana, Bull. Chem. Soc. Jpn., 52, 2084 (1979).
K. Dwarakanath and D. N. Sathyanarayana, Indian J. Pure Appl. Phys., 17, 171 (1979).
K. Ravindranath and K. V. Ramiah, Indian J. Pure Appl. Phys., 17, 509 (1979).
K. Dwarakanath and D. N. Sathyanarayana, Indian J. Chem., A, 18, 302 (1979).
K. Dwarakanath and D. N. Sathyanarayana, Bull. Chem. Soc. Jpn., 52, 2699 (1979).
G. Mille, J. Neumann, G. Assef, and J. Kister, Compt. Rend., C, 285, 175 (1977).
G. Mille, J. Kister, G. Assef, and J. Chouteau, Compt. Rend., C, 286, 477 (1978).
G. Mille, M. Guiliano, G. Assef, and J. Kister, Compt. Rend., B, 286, 105 (1978).
L. Bellamy, Infrared Spectra of Complex Molecules, Methuen, London (1958).
L. Bellamy, New Data on the IR Spectra of Complex Molecules [Russian translation], Mir, Moscow (1971), p. 232.
T. I. Kirichenko, A. V. Bogatskii, and N. G. Luk'yanenko, Dokl. Akad. Nauk SSSR, 255, 594 (1980).
B. Singh, D. K. Sharma, U. S. P. Sharma, and B. K. Sharma, J. Indian Chem. Soc., 56, 764 (1979).
A. K. Chibisov and Yu. A. Pentin, Zh. Obshch. Khim., 31, 11 (1961).
A. K. Chibisov and Yu. A. Pentin, Zh. Obshch. Khim., 31, 359 (1961).
S. Oae, The Chemistry of Organic Sulfur Compounds [Russian translation], Khimiya, Moscow (1975).
J. Sawlewicz and K. Wisterowicz, Acta Pol. Pharm., 33, 557 (1976).
J. Sawlewicz and K. Wisterowicz, Acta Pol. Pharm., 33, 551 (1976).
J. Sawlewicz, K. Wisterowicz, and H. Ciurak, Acta Pol. Pharm., 33, 681 (1976).
J. E. Baer and R. G. Lockwood, J. Am. Chem. Soc., 76, 1162 (1954).
J. Kister, G. Assef, J. Mille, and J. Metzger, Can. J. Chem., 57, 813 (1979).
F. D'Angeli, C. Bello, and V. Giormani, Gazz. Chim. Ital., 94, 1342 (1964).
M. Fefer and L. C. King, J. Org. Chem., 26, 828 (1961).
C. J. Sharpe, R. S. Shadbolt, A. Ashford, and J. W. Ross, J. Med. Chem., 14, 977 (1971).
V. P. Arya, K. Nagarajan, J. David, S. J. Shenoy, and N. G. Gokhale, Indian J. Chem., B, 16, 226 (1978).
R. C. Tweit, US Patent No. 2969362; Ref. Zh. Khim., 7L318 (1962).
R. S. Aspinall and E. J. Bianco, J. Am. Chem. Soc., 73, 602 (1951).
N. G. Luk'yanenko, A. V. Bogatskii, T. I. Kirichenko, and S. V. Shcherbakov, Zh. Org. Khim., 17, 1279 (1981).
R. J. Hayward, M. Htay, and O. Meth-Cohn, Chem. Ind., No. 10, 373 (1977).
L. I. Mizrakh, L. Yu. Polonskaya, and B. I. Bryantsev, Zh. Obshch. Khim., 47, 1194 (1977).
A. V. Bogatskii (Bogatsky), N. G. Luk'yanenko (Lukyanenko), and T. I. Kirichenko, Synthesis, No. 6, 464 (1982).
P. N. Gordon, US Patent 3219522; Chem. Abstr., 64, 6671 (1966).
S. C. Bell and P. H. L. Wei, J. Med. Chem., 19, 524 (1976).
G. R. Hansen and F. D. Blake, J. Heterocycl. Chem., 7, 997 (1970).
A. Kosasayama, F. Konno, K. Higashi, and F. Ishikawa, Chem. Pharm. Bull., 27, 841 (1979).
H. A. Hageman and J. A. Ridell, US Patent 3146240; Ref. Zh. Khim., 20N520P (1966).
C. K. Cain, US Patent No. 2742481; Ref. Zh. Khim., 51328P (1958).
R. Hiltmann, H. Wollweber, and G. Herman, US Patent No. 3984039; Izobr. Rubezhom, 18, No. 18 (1975).
G. Hornyak, K. Lempert, and G. Simic, Kem. Kozlemenyek, 33, 81 (1970).
A. Safaev, A. Kadyrov, Z. G. Saidaliev, and T. F. Faiziev, British Patent No. 1535143; Izobr. SSSR Rubezhom, 55, No. 14 (1979).
A. V. El'tsov, K. M. Krivozheiko, and M. B. Kolesova, Zh. Org. Khim., 4, 308 (1968).
A. V. El'tsov, and K. M. Krivozheiko, Zh. Org. Khim., 6, 635 (1970).
G. Assef, J. Kister, G. Mille, and J. Metzger, Compt. Rend., C, 284, 273 (1977).
J. Kister, G. Assef, G. Mille, and J. Metzger, Can. J. Chem., 57, 822 (1979).
J. G. Roberts, J. Chem. Soc., No. 1, 176 (1964).
G. Bello, V. Giormani, and F. D'Angeli, Gazz. Chim. Ital., 97, 787 (1967).
H. Kohn, J. Am. Chem. Soc., 98, 3690 (1976).
H. Kohn, J. Org. Chem., 42, 72 (1977).
M. R. Willcott, J. Org. Chem., 42, 941 (1977).
A. E. Dixon and J. Taylor, J. Chem. Soc., 117, 720 (1920).
M. L. Moore and F. S. Crossley, J. Am. Chem. Soc., 62, 3273 (1940).
A. Bose, J. C. Kapur, and M. S. Manhas, Synthesis, No. 12, 891 (1974).
J. Sawlewicz, K. Wisterowicz, and M. Janowiec, Acta Pol. Pharm., 35, 403 (1978).
J. Sawlewicz, K. Wisterowicz, and M. Janowiec, Acta Pol. Pharm., 35, 413 (1978).
F. D'Angeli, Gazz. Chim. Ital., 95, 735 (1965).
F. D'Angeli, A. Bandel, and V. Giormani, J. Org. Chem., 28, 1596 (1963).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 723–737, June, 1983.
Rights and permissions
About this article
Cite this article
Bogatskii, A.V., Luk'yanenko, N.G. & Kirichenko, T.I. Cyclic thioureas (review). Chem Heterocycl Compd 19, 577–589 (1983). https://doi.org/10.1007/BF00523064
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00523064