Abstract
The reaction of diethyl chloroethynylphosphonate with methyl (ethyl) 6-methyl-4-aryl-2-thio-1,2,3,4-tetrahydropyrimidine-5-carboxylate proceeded through the replacement of the chlorine atom and subsequent intramolecular cyclization to yield methyl (ethyl) 3-(diethoxyphosphoryl)-5-aryl-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates.
REFERENCES
Alam, O., Khan, S.A., Siddiqui, N., and Ahsan, W., Med. Chem. Res., 2010, vol. 19, p. 1245. https://doi.org/10.1007/s00044-009-9267-8
Geist, J.G., Lauw, S., Illarionova, V., Illarionov, B., Fischer, M., Grwert, T., Rohdich, F., Eisenreich, W., Kaiser, J., Groll, M., Scheurer, C., Wittlin, S., Alonso-Gomez, J.L., Schweizer, W.B., Bacher, A., and Diederich, F., ChemMedChem, 2012, vol. 5, no. 7, p. 1092. https://doi.org/10.1002/cmdc.201000083
Tozkoparan, B., Ertan, M., Kelicen, P., and Demirdamar, R., Il Farmaco, 1999, vol. 54, p. 588. https://doi.org/10.1016/s0014-827x(99)00068-3
Keshari, A.K., Singh, A.K., and Saha, S., Mini-Rev. Med. Chem., 2017, vol. 17, no. 15, p. 1488. https://doi.org/10.2174/1389557517666170216142113
Mobinikhaledi, A., Foroughifar, N., and Ahmadi, B., Phosphorus, Sulfur, Silicon, Relat. Compd., 2005, vol. 180, p. 339. https://doi.org/10.1080/104265090508406
Nagarajaih, H., Khazi, I.M., and Begum, N.S., J. Chem. Sci., 2012, vol. 124, no. 4, p. 847. https://doi.org/10.1007/s12039-012-0271-z
Zhi, H., Chen, L., Zhang, L., Liu, S., Wan, D.C.C., Lin, H., and Hu, C., Arkivoc, 2008, vol. 2008, no. 13, p. 266. https://doi.org/10.3998/ark.5550190.0009.d29
Fatima, S., Sharma, A., Sharma, R., and Tripathi, R.P., J. Heterocycl. Chem., 2012, vol. 49, p. 600. https://doi.org/10.1002/jhet.831
Egorov, D.M., Piterskaya, Y.L., Dogadina, A.V., and Svintsitskaya, N.I., Tetrahedron Lett., 2015, vol. 56, no. 12, p. 1552. https://doi.org/10.1016/j.tetlet.2015.02.027
Egorov, D.M., Piterskaya, Yu.L., Erkhitueva, E.B., Svintsitskaya, N.I., and Dogadina, A.V., Russ. J. Gen. Chem., 2017, vol. 87, no. 9, p. 1924. https://doi.org/10.1134/S1070363217090067
Funding
This work was financially supported by the Russian Foundation for Basic Research (grant no. 18-33-00430) in the framework of the basic part of the governmental task of the Ministry of Science and Higher Education (no. 4.554.2017/8.9) using the equipment of the Engineering Center of the St. Petersburg State Institute of Technology.
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Egorov, D.M., Babushkina, A.A., Leonenok, V.E. et al. Synthesis of 3-Phosphorylated Thiazolo[3,2-a]pyrimidine-6-carboxylates. Russ J Gen Chem 90, 319–321 (2020). https://doi.org/10.1134/S1070363220020267
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DOI: https://doi.org/10.1134/S1070363220020267