Abstract
Condensation of the N-(3,5-dichloropyridyl-2)- and N-(benzothiazolyl-2-thioacetyl)hydrazones of carbonyl compounds with thioglycolic acid gave the 3-(3,5-dichloropyridyl-2)amino- and 3-[N-(benzothiazolyl-2-thioacetyl)amino]-2-R1-2-R2-thiazolidin-4-ones. Reaction of 1-(benzothiazolyl-2-thioacetyl)-4-R-thiosemicarbazides with chloroacetic acid in the presence of sodium acetate gave the 2-[N-(benzothiazolyl-2-thioacetyl)hydrazono]-3-R-thiazolidin-4-ones. It was found that the N-(benzothiazolyl-2-thioacetyl)hydrazones, both in the solid state and in solution, exist in the form of an equilibrium mixture of the EZ'- and EE'-isomers as a result of hindered rotation around the amide N-CO bond.
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REFERENCES
K. N. Batt, A. M. Dave, N. K. Undavia, and P. B. Trivedi, J. Indian Chem. Soc., 66, 181 (1989)
P. Monforte, S. Grasso, A. Chimirri, and G. Fenech, Farmaco, Ed. Sci., 36, No. 2, 109 (1981)
S. V. Patel, J. N. Vasavada, and G. B. Joshi, J. Indian Chem. Soc., 61, 560 (1984)
G. C. Kamdar, D. J. Bhatt, and A. R. Parikh, J. Indian Chem. Soc., 65, 67 (1988)
C. L. Patel and H. Parekh, J. Indian Chem. Soc., 65, 282 (1988)
M. I. Husain and S. Shukla, Indian J. Chem., 25B, 549 (1986)
L. Mehta and H. Parekh, J. Indian Chem. Soc., 65, 65 (1988)
P. N. Dhal, T. E. Achary, and K. Naya, J. Indian Chem. Soc., 51, 931 (1974)
V. I. Minkin, Yu. A. Zhdanov, and E. A. Medyantseva, Azomethines [in Russian], Rostov State University Publishing House, Rostov-on Don, 1967
D. J. R. Massy, Synthesis, 589 (1987)
Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974)
G. R. Rao, M. T. Chary, K. Mogilaiah, B. Swamy, and B. Sreenivasulu, J. Indian Chem. Soc., 66, 61 (1989)
V. K. Srivastava, S. Singh, P. Kumar, and K. Shanker, J. Indian Chem. Soc., 25B, 769 (1986)
R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric Identification of Organic Compounds [Russian translation], Mir, Moscow (1977)
S. I. Yakimovich, V. N. Nikolaev, and O. A. Afonina, Zh. Org. Khim., 15, 922 (1979)
K. N. Zelenin, V. V. Pinson, A. A. Potekhin, I. P. Bezhan, V. A. Khrustalev, and P. S. Lobanov, Zh. Org. Khim., 14, 490 (1978)
S. A. Rutavichyus, S. P. Valyulene, and V. V. Mozolis, Zh. Org. Khim., 23, 1198 (1987)
S. A. Flegontov, Z. S. Titova, B. I. Buzykin, and Yu. P. Kitaev, Izv. Akad. Nauk SSSR. Ser. Khim., 559 (1976)
D. Hadzi and J. Jan, Spectrochim. Acta, 23A, 571 (1967)
N. P. Bezhan, V. A. Khrustalev, K. N. Zelenin, and B. P. Nikolaev, Zh. Org. Khim., 14, 754 (1978)
A. R. Katritzky (editor), Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Khimiya, Moscow, Leningrad (1966)
M. A. Silin, V. I. Kelarev, and V. Abu-Ammar, Khim. Geterotsikl. Soedin., 256 (2000)
J. R. Dyer, Applications of Absorption Spectroscopy of Organic Compounds [Russian translation], Khimiya, Moscow (1970)
B. R. Rani, U. T. Bhalerao, and M. F. Rahman, Indian J. Chem., 29B, 995 (1990)
M. Sen, N. Mishra, and A. Nayak, J. Indian Chem. Soc., 67, 409 (1990)
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Kelarev, V.I., Silin, M.A., Kotova, I.G. et al. Synthesis of N-Substituted 3-Aminothiazolidin-4-ones Containing Hetaryl Fragments. Chemistry of Heterocyclic Compounds 39, 213–222 (2003). https://doi.org/10.1023/A:1023772509165
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DOI: https://doi.org/10.1023/A:1023772509165