Synthesis and phosphonylation of 6-methyl-4-aryl-2-thio-1,2,3,4-tetrahydropyrimidine5-carboxylic acids ethyl esters
- Authors: Nosova N.A.1, Skrylkova A.S.1, Egorov D.M.1
- 
							Affiliations: 
							- St. Petersburg State Technological Institute (Technical University)
 
- Issue: Vol 93, No 9 (2023)
- Pages: 1358-1364
- Section: Articles
- URL: https://rjpbr.com/0044-460X/article/view/667314
- DOI: https://doi.org/10.31857/S0044460X23090068
- EDN: https://elibrary.ru/WYCAYG
- ID: 667314
Cite item
Abstract
A new series of 6-methyl-4-aryl-2-thio-1,2,3,4-tetrahydropyrimidine-5-carboxylic acids ethyl esters was synthesized. The reaction of the obtained esters with dimethyl 2-chloroethynylphosphonate leads to the selective formation of new ethyl 3-(dimethoxyphosphoryl)-5-aryl-7-methyl-5 H -thiazolo[3,2- a ]pyrimidine-6-carboxylates.
			                About the authors
N. A. Nosova
St. Petersburg State Technological Institute (Technical University)
A. S. Skrylkova
St. Petersburg State Technological Institute (Technical University)
D. M. Egorov
St. Petersburg State Technological Institute (Technical University)
														Email: diavoly@mail.ru
				                					                																			                												                														
References
- Bhat M.A., Al-Omar M.A., Naglah A.M., Al-Dhfyan A. // J. Chem. 2020. Vol. 2020. P. 1. doi: 10.1155/2020/4284628
- Khaldi-Khellafi N., Makhloufi-Chebli M., Oukacha-Hikem D., Bouaziz S.T., Lamara K.O., Idir T., Benazzouz-Touami A., Dumas F. // J. Mol. Struct. 2019. Vol. 1181. P. 261. doi: 10.1016/j.molstruc.2018.12.104
- Bhat M.A., Al-Omar M.A., Khan A.A., Alanazi A.M., Naglah A.M. // Drug Design Dev. Ther. 2019. Vol. 2019. N 13. P. 2393. doi: 10.2147/DDDT.S198865
- Krishna B., Payra S., Roy S. // J. Colloid Interface Sci. 2022. Vol. 607. P.729. doi: 10.1016/j.jcis.2021.09.031
- Bhat M.A., Al-Omar M.A., Ghabbour H.A., Naglah A.M. // Molecule. 2018. Vol. 23. P. 1559. doi: 10.3390/molecules23071559
- Mathapati S.R., Prasad D., Atar A.B., Nagaraja B.M., Dawle J.K., Jadhav A.H. // Mater. Today Proceed. 2019. Vol. 9. P. 661. doi: 10.1016/j.matpr.2018.10.390
- Kazemi M. // Synth. Commun. 2020. Vol. 50. N 10. P. 1409. doi: 10.1080/00397911.2020.1720740
- Dowarah J., Patel D., Marak B.N., Yadav U.C.S., Shah P.K., Shukla P.K., Singh V.P. // RSC Adv. 2021. Vol. 11. P. 35747. doi: 10.1039/d1ra03969e
- Ilyas U., Nazir B., Altaf R., Muhammad S.A., Zafar H., Paiva-Santos A.C., Abbas M., Duan Y. // Front. Endocrin. 2022. Vol. 13. P. 1. doi: 10.3389/fendo.2022.1022623
- Matos L.H.S., Masson F.T., Simeoni L.A., Homem-de-Mello M. // Eur. J. Med. Chem. 2018. Vol. 143. P. 1779. doi: 10.1016/j.ejmech.2017.10.073
- Marinescu M. // Molecule. 2021. Vol. 26. P. 6022. doi: 10.3390/molecules26196022
- Shipilovskikh S.A., Rubtsov A.E. // J. Org. Chem. 2019. Vol. 84. N 24. P. 15788. doi: 10.1021/acs.joc.9b00711
- Maliga Z., Kapoor T.M., Mitchison T.J. // Chem. Biol. 2002. Vol. 9. N 9. P. 989. doi: 10.1016/S1074-5521(02)00212-0
- Sun X., Shi X., Sun X., Luo Y., Wu X., Yao C., Yu H., Li D., Liu M., Zhou J. // Acta Pharmacol. Sinica. 2011. Vol. 32. N 12. P. 1543. doi: 10.1038/aps.2011.130
- Bourne C.R., Finn M.G., Zlotnick A. // J. Virol. 2006. Vol. 80. N 22 P. 11055. doi: 10.1128/JVI.00933-06
- Atwal K.S., Swanson B.N., Unger S.E., Floyd D.M., Moreland S., Hedberg A., O'Reilly B.C. // J. Med. Chem. 1991. Vol. 34. N 2. P. 806. doi: 10.1021/jm00106a048
- Siutkina A.I., Chashchina S.V., Kizimova I.A., Igidov N.M., Makhmudov R.R., Shipilovskikh S.A. // Russ. J. Org. Chem. 2021. Vol. 57. N 11. P. 1874. doi: 10.1134/S1070428021110105
- Mourad A.K., Mohammed F.K., Tammam G.H., Mohammed S.R. // J. Heterocycl. Chem. 2019. Vol. 56. N 8. P. 2262. doi: 10.1002/jhet.3621
- Singh K., Singh K., Trappanese D.M., Moreland R.S. // Eur. J. Med. Chem. 2012. Vol. 54. P. 397. doi: 10.1016/j.ejmech.2012.05.017
- Essid I., Touil S. // Arkivoc. 2013. Vol. 4. P. 98. doi: 10.3998/ark.5550190.p007.871
- Essid I., Lahbib K., Kaminsky W., Nasr C.B., Touil S. // J. Mol. Struct. 2017. Vol. 1142. P. 130. doi: 10.1016/j.molstruc.2017.04.054
- Kaskevich K.I., Babushkina A.A., Gurzhiy V.V., Egorov D.M., Svintsitskaya N.I., Dogadina A.V. // Beilstein J. Org. Chem. 2020. Vol. 16. P. 1947. doi: 10.3762/bjoc.16.161
- Babushkina A.A., Dogadina A.V., Egorov D.M., Piterskaia J.L., Shtro A.A., Nikolaeva Y.V., Galochkina A.V., Kornev A.A., Boitsov V.M. // Med. Chem. Res. 2021. Vol. 30. N 12. P. 2203. doi: 10.1007/s00044-021-02801-x
- Егоров Д.М., Бабушкина А.А., Леоненок В.Е., Чекалов А.П., Питерская Ю.Л. // ЖОХ. 2020. Т. 90. № 2. С. 326.
- Egorov D.M., Babushkina A.A., Leonenok V.E., Chekalov A.P., Piterskaya Yu.L. // Russ. J. Gen. Chem. 2020. Vol. 90. N 2. P. 319. doi: 10.1134/S1070363220020267
Supplementary files
 
				
			 
					 
						 
						 
						 
						 
									

 
  
  
  Email this article
			Email this article 
 Open Access
		                                Open Access Access granted
						Access granted Subscription or Fee Access
		                                							Subscription or Fee Access
		                                					