Solid-Phase Synthesis of Triethylammonium Salt of 4-Oxothiazolidine-2-thione

Solid-Phase Synthesis of Triethylammonium Salt of 4-Oxothiazolidine-2-thione Russian Journal of Applied Chemistry, Vol. 75, No. 4, 2002, p. 672. Translated from Zhurnal Prikladnoi Khimii, Vol. 75, No. 4, 2002, p. 685. Original Russian Text Copyright C 2002 by Aronova, Ginak. BRIEF ˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝ ˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝ COMMUNICATIONS Solid-Phase Synthesis of Triethylammonium Salt of 4-Oxothiazolidine-2-thione E. B. Aronova and A. I. Ginak St. Petersburg State Technological Institute, St. Petersburg, Russia Received December 23, 2001; in final form, January 2002 Abstract-A procedure was developed for solid-phase synthesis of triethylammonium salt of 4-oxothiazol- idine-2-thione. 3-R-Substituted 4-oxothiazolidinethiones are natu- H N C= O (C H ) N H N C= O (C H ) N 2 5 3 2 5 3 ral biologically active substances. They are plant CH CH S= C S= C ! 2 ! 2 S S growth stimulants [1] and metabolites of amino acid I II synthesis in cells [2]; their synthetic analogs exhibit 10% HCl a wide spectrum of biological activity, from herbicides c c 77 6 I +[(C H ) NH]Cl 2 5 3 [3] to antitumor agents [4]; also, these compounds are The resulting product contains no impurities and used as complexones for noble metals. The main syn- does not require additional purification. Its composi- thetic route to these compounds involves nucleophilic tion was confirmed by elemental analysis, and the substitution in polar solvents in the presence of bases. structure, by a mixing test with an authentic sample. In the process, the main reaction of electrophile ad- dition to the sulfur or nitrogen atom of the heterocycle Found, (%): N 11.8, S 27.3. is accompanied by base hydrolysis of the initial and C H N OS . 9 18 2 2 final products with ring cleavage. This side reaction Calculated (%): N 12.0, S 27.4. significantly decreases the yield of the target products and complicates their purification. It is known [5] that REFERENCES the nucleophilic substitution is preceded by the forma- tion of salts of the substrate with a base, and in some 1. Brown, F.C., Chem. Rev., 1961, vol. 61, no. 5, cases, these intermediate salts are isolated to prevent pp. 463 3521. hydrolysis. However, synthesis of these salts is also 2. Zvonkova, E.N., Zotchik, N.V., Fillipovich, E.N., et al., labor-consuming and requires proper choice of sol- Khimiya biologicheski aktivnykh prirodnykh soedinenii vents for neutralization and crystallization. (Chemistry of Biologically Active Natural Compounds), Moscow: Khimiya, 1970. To eliminate these drawbacks, we attempted to pre- 3. Mel’nikov, N.N., Volkov, A.I., and Korotkova, O.A., pare alkylammonium salt of 4-oxothiazolidine-2-thi- Pestitsidy i okruzhayushchaya sreda (Pesticides and one by solid-phase synthesis. Crystalline 4-oxothiazo- the Environment), Leningrad: Khimiya, 1977. lidine-2-thione I was treated with triethylamine vapor 4. Pluijgers, C.N., Berg, J., and Thorn, D.D., Recl. Trav. at 50 3120oC in a tubular reactor with false bottom. Chim. Pays-Bas, 1969, vol. 88, no. 1, pp. 2413253. The reaction gives no by-products, and the desired 5. Ginak, A.I., Volkova, A.A., Ramsh, S.M., and Sochi- 4-oxothiazolidine-2-thione triethylammonium salt II lin, E.G., Zh. Org. Khim., 1980, vol. 16, no. 1, is formed in 98% yield. pp. 1223125. 1070-4272/02/7504-0672 $27.00 C 2002 MAIK [Nauka/Interperiodica] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Journal of Applied Chemistry Springer Journals

Solid-Phase Synthesis of Triethylammonium Salt of 4-Oxothiazolidine-2-thione

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Kluwer Academic Publishers-Plenum Publishers
Copyright
Copyright © 2002 by MAIK “Nauka/Interperiodica”
Subject
Chemistry; Chemistry/Food Science, general
ISSN
1070-4272
eISSN
1608-3296
D.O.I.
10.1023/A:1019502122008
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Abstract

Russian Journal of Applied Chemistry, Vol. 75, No. 4, 2002, p. 672. Translated from Zhurnal Prikladnoi Khimii, Vol. 75, No. 4, 2002, p. 685. Original Russian Text Copyright C 2002 by Aronova, Ginak. BRIEF ˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝ ˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝˝ COMMUNICATIONS Solid-Phase Synthesis of Triethylammonium Salt of 4-Oxothiazolidine-2-thione E. B. Aronova and A. I. Ginak St. Petersburg State Technological Institute, St. Petersburg, Russia Received December 23, 2001; in final form, January 2002 Abstract-A procedure was developed for solid-phase synthesis of triethylammonium salt of 4-oxothiazol- idine-2-thione. 3-R-Substituted 4-oxothiazolidinethiones are natu- H N C= O (C H ) N H N C= O (C H ) N 2 5 3 2 5 3 ral biologically active substances. They are plant CH CH S= C S= C ! 2 ! 2 S S growth stimulants [1] and metabolites of amino acid I II synthesis in cells [2]; their synthetic analogs exhibit 10% HCl a wide spectrum of biological activity, from herbicides c c 77 6 I +[(C H ) NH]Cl 2 5 3 [3] to antitumor agents [4]; also, these compounds are The resulting product contains no impurities and used as complexones for noble metals. The main syn- does not require additional purification. Its composi- thetic route to these compounds involves nucleophilic tion was confirmed by elemental analysis, and the substitution in polar solvents in the presence of bases. structure, by a mixing test with an authentic sample. In the process, the main reaction of electrophile ad- dition to the sulfur or nitrogen atom of the heterocycle Found, (%): N 11.8, S 27.3. is accompanied by base hydrolysis of the initial and C H N OS . 9 18 2 2 final products with ring cleavage. This side reaction Calculated (%): N 12.0, S 27.4. significantly decreases the yield of the target products and complicates their purification. It is known [5] that REFERENCES the nucleophilic substitution is preceded by the forma- tion of salts of the substrate with a base, and in some 1. Brown, F.C., Chem. Rev., 1961, vol. 61, no. 5, cases, these intermediate salts are isolated to prevent pp. 463 3521. hydrolysis. However, synthesis of these salts is also 2. Zvonkova, E.N., Zotchik, N.V., Fillipovich, E.N., et al., labor-consuming and requires proper choice of sol- Khimiya biologicheski aktivnykh prirodnykh soedinenii vents for neutralization and crystallization. (Chemistry of Biologically Active Natural Compounds), Moscow: Khimiya, 1970. To eliminate these drawbacks, we attempted to pre- 3. Mel’nikov, N.N., Volkov, A.I., and Korotkova, O.A., pare alkylammonium salt of 4-oxothiazolidine-2-thi- Pestitsidy i okruzhayushchaya sreda (Pesticides and one by solid-phase synthesis. Crystalline 4-oxothiazo- the Environment), Leningrad: Khimiya, 1977. lidine-2-thione I was treated with triethylamine vapor 4. Pluijgers, C.N., Berg, J., and Thorn, D.D., Recl. Trav. at 50 3120oC in a tubular reactor with false bottom. Chim. Pays-Bas, 1969, vol. 88, no. 1, pp. 2413253. The reaction gives no by-products, and the desired 5. Ginak, A.I., Volkova, A.A., Ramsh, S.M., and Sochi- 4-oxothiazolidine-2-thione triethylammonium salt II lin, E.G., Zh. Org. Khim., 1980, vol. 16, no. 1, is formed in 98% yield. pp. 1223125. 1070-4272/02/7504-0672 $27.00 C 2002 MAIK [Nauka/Interperiodica]

Journal

Russian Journal of Applied ChemistrySpringer Journals

Published: Oct 13, 2004

References

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