Synthesis of functional derivatives of chlorine-substituted isothiazoles.
https://doi.org/10.29235/1561-8331-2024-60-3-215-221
Abstract
Optimal procedures have been developed for the synthesis of substituted isothiazoles containing an active chlorine atom in position 5 of the heterocycle and various functional groups in position 3: carboxyl, hydroxymethyl, aldehyde. Based on these methods, previously undescribed compounds were obtained: 5-morpholino-substituted 3-hydroxymethyl-4- chloroisothiazole, 4-chloroisothiazole-3-carboxylic acid and its methyl ester. The resulting substances are reactive building blocks for organic synthesis of compounds with a high potential for biological activity.
About the Authors
E. N. Margun
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Margun Ekaterina N. – Junior Researcher
13, Surganov Str., 220072, Minsk
I. A. Kolesnik
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Kolesnik Irina A. – Ph. D. (Chemistry), Senior Researcher
13, Surganov Str., 220072, Minsk
E. A. Akishina
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Akishina Ekaterina A. – Researcher
13, Surganov Str., 220072, Minsk
E. A. Dikusar
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Dikusar Evgenij A. – Ph. D. (Chemistry), Senior Researcher
13, Surganov Str., 220072, Minsk
N. A. Logvinenko
RUDN University
Russian Federation
Russian Federation
Logvinenko Nikita A. – student
6, Miklukho-Maklay Str., 117198, Moscow
N. S. Volchkov
RUDN University
Russian Federation
Russian Federation
Volchkov Nikita S. – student
6, Miklukho-Maklay Str., 117198, Moscow
V. I. Potkin
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Potkin Vladimir I. – Dr. Sci. (Chemistry), Professor, Academician, Head of the Laboratory
13, Surganov Str., 220072, Minsk
References
1. Mokrushin V. S., Vavilov G. А Fundamentals of chemistry and technology of bioorganic and synthetic drugs. Sankt-Peterburg, Prospect nauki Publ., 2009. 496 p. (in Russian).
2. Kletskov, A. V., Bumagin, N. A., Zubkov, F. I., Grudinin, D. G., Potkin, V. I. Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes. Synthesis, 2020, vol. 52, no. 2, pp. 159–188. https://doi.org/10.1055/s-0039-1690688
3. Kulchitsky V. A., Potkin V. I., Zubenko Y. S., Chernov A. N., Talabaev M. V., Demidchik Y. E., Petkevich S. K., Kazbanov V. V., Gurinovich T. A., Roeva M. O., Grigoriev D. G., Kletskov A. V., Kalunov V. N. Cytotoxic Effects of Chemotherapeutic Drugs and Heterocyclic Compounds at Application on the Cells of Primary Culture of Neuroepithelium Tumors. Medicinal Chemistry, 2012, vol. 8, no. 1, pp. 22–32. https://doi.org/10.2174/157340612799278298
4. Kulchitsky V., Zamaro A., Potkin V., Suziedelis K., Koulchitsky S., Kaliadzich Zh. Perspectives of Conjoint Application of Heterocyclic Compounds and Classical Chemotherapeutic Agents. Journal of Cancer Science and Trerapy, 2020, vol. 2, no. 2, pp. 119–120. Available at: https://www.scitcentral.com/article/25/1106/atozJournals.php (accessed 25 May 2024).
5. Potkin V. I., Kletskov A. V., Zubkov F. I. Isothiazoles. Comprehensive Heterocyclic Chemistry IV, 2020, vol. 4, pp. 482–529. https://doi.org/10.1016/B978-0-12-818655-8.00127-X
6. Potkin V.I., Petkevich, S. K., Kletskov, A. V., Dikusar E. A., Zubenko, Y. S., Zhukovskaya N.A., Kаzbanov V. V., Pashkevich S. G. Synthesis of functionally substituted hydroxy derivatives of isoxazoles and isothiazoles. Russian Journal of Organic Chemistry, 2013, vol. 49, рр. 1523–1533. https://doi.org/10.1134/s1070428013100205
7. Bolm C., Magnus A. S., Hildebrand J. P. Catalytic Synthesis of Aldehydes and Ketones under Mild Conditions Using TEMPO/Oxone. Organic Letters, 2000, vol. 2, no. 8, pp. 1173–1175. https://doi.org/10.1021/ol005792g
8. Zlatoidsky P. Preparation of N2-protected amino acid aldehydes via reduction of corresponding acid halides with lithium tris-(tert.butoxy)-aluminium hydride. Tetrahedron Letters, 1995, vol. 36, no. 40, pp. 7281–7284. https://doi.org/10.1016/0040-4039(95)01464-S
9. Corey E. J., Suggs J. W. Pyridinium Chlorochromate. An Efficient Reagent for Oxidation of Primary and Secondary Alcohols to Carbonyl Compounds. Tetrahedron Letters, 1975, vol. 31, no. 16, pp. 2647–2650. https://doi.org/10.1016/S0040-4039(00)75204-X
10. Tidwell T. T. Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: The Moffatt, Swern, and Related Oxidations. Organic Reactions, 1990, vol. 39, pp. 297–555. https://doi.org/10.1002/0471264180.OR039.03
11. Pfitzner K. E., Moffatt J. G. A New and Selective Oxidation of Alcohols. Journal of American Chemical Society, 1963, vol. 85, no. 19, pp. 3027–3028. https://doi.org/10.1021/ja00902a036
12. Pfitzner K. E., Moffatt J. G. Sulfoxide-Carbodiimide Reactions. I. A Facile Oxidation of Alcohols. Journal of American Chemical Society, 1965, vol. 87, no. 24, pp. 5661–5670. https://doi.org/10.1021/ja00952a026
13. Zubenko Y. S., Kletskov A.V., Potkin V. I., Zvereva T. D., Zhukovskaya N. A., Zolotar R. M., Chepik О. P. Synthesis and pesticidal activity in composition with kerber insecticide of 5-methoxy(hydroxy)-substituted 4-chloroisothiazole-3-carboxylic acids and their methyl esters. Vestsi Natsyyanal’nai akademii navuk Belarusi. Seryya khimichnykh navuk = Proceedings of the National Academy of Sciences of Belarus. Chemical series, 2011, no. 4, pp. 53‒58 (in Russian).
14. Zubenko Yu. S., Potkin V. I. Efficient Fluoride-Mediated Synthesis of 5-Amino-Substituted Isothiazoles. Synthesis, 2009, no. 14, pp. 1361–1364. https://doi.org/10.1055/s-0029-1216844
Review
Views: 967
Email this article 