5-Substituted (1,3-thiazolidin-2-ylidene)ketones react regioselectively with 1-chlorobenzyl isocyanates under mild conditions to form diastereomeric 8-acyl-2,3,6,7-tetrahydro-5H-[1,3]thiazolo[3,2-c]pyrimidin-5-ones, the relative configuration of the chiral centers of which was determined by X-ray structural analysis.
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(a) Kappe, C. O. Eur. J. Med. Chem.2000, 35, 1043. (b) Kappe, C. O. QSAR Comb. Sci.2003, 22, 630. (c) Sandhu, S.; Sandhu, J. S. ARKIVOC2012, (i), 66. (d) Shkurko, O. P.; Tolstikova, T. G.; Sedova, V. F. Russ. Chem. Rev.2016, 85, 1056. [Usp. Khim.2016, 85, 1056.] (e) Nagarajaiah, H.; Mukhopadhyay, A.; Moorthy, J. N. Tetrahedron Lett.2016, 57, 5135.
(a) Ashok, M.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem.2007, 42, 380. (b) Zhao, D.; Chen, C.; Liu, H.; Zheng, L.; Tong, Y.; Qu, D.; Han, S. Eur. J. Med. Chem.2014, 87, 500.
Ghorab, M. M.; Mohamed, Y. A.; Mohamed, S. A.; Ammar, Y. A. Phosphorus, Sulfur Silicon Relat. Elem.1996, 108, 249.
Geist, J. G.; Lauw, S.; Illarionova, V.; Illarionov, B.; Fischer, M.; Gräwert, T.; Rohdich, F.; Eisenreich, W.; Kaiser, J.; Groll, M.; Scheurer, C.; Wittlin, S.; Alonso-Gómez, J. L.; Schweizer, W. B.; Bacher, A.; Diederich, F. ChemMedChem2010, 5, 1092.
Fatima, S.; Sharma, A.; Saxena, R.; Tripathi, R.; Shukla, S. K.; Pandey, S. K.; Tripathi, R.; Tripathi, R. P. Eur. J. Med. Chem.2012, 55, 195.
(a) Tozkoparan, B.; Ertan, M.; Krebs, B.; Läge, M.; Kelicen, P.; Demirdamar, R. Arch. Pharm.1998, 331, 201. (b) Tozkoparan, B.; Ertan, M.; Kelicen, P.; Demirdamar, R. Farmaco1999, 54, 588.
Holla, B. S.; Rao, B. S.; Sarojini, B. K.; Akberali, P. M. Eur. J. Med. Chem.2004, 39, 777.
Wichmann, J.; Adam, G.; Kolczewski, S.; Mutel, V.; Woltering, T. Bioorg. Med. Chem. Lett.1999, 9, 1573.
Furrer, H.; Granzer, E.; Wagner, R. Eur. J. Med. Chem.1994, 29, 819.
(a) Duron, S. G.; Gin, D. Y. Org. Lett.2001, 3, 1551. (b) Shimokawa, J.; Shirai, K.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Angew. Chem., Int. Ed.2004, 43, 1559. (c) Arnold, M. A.; Day, K. A.; Durón, S. G.; Gin, D. Y. J. Am. Chem. Soc.2006, 128, 13255. (d) Nakazaki, A.; Nakane, Y.; Ishikawa, Y.; Yotsu-Yamashita, M.; Nishikawa, T. Org. Biomol. Chem.2016, 14, 5304. (e) Jamison, M. T.; Molinski, T. F. J. Nat. Prod.2015, 78, 557. (f) Singh, K.; Singh, S. Tetrahedron2008, 64, 11718. (g) Guo, Y.; Gao, Z.; Fan, C.; Chen, J.; Li, J.; Huang, Y.; Huang, G.; Yu, H.; Zou, C. Synthesis2018, 2394.
Elliott, M. C.; Monk, A. E.; Kruiswijk, E.; Hibbs, D. E.; Jenkins, R. L.; Jones, D. V. Synlett1999, 1379.
(a) Zhou, A.; Pittman, C. U. Tetrahedron Lett.2005, 46, 2045. (b) Zhou, A.; Pittman, C. U. Synthesis2006, 37. (c) Pontillo, J.; Chen, C. Bioorg. Med. Chem. Lett.2005, 15, 1407. (d) De Silva, H. I.; Chatterjee, S.; Henry, W. P.; Pittman, C. U. Synthesis2012, 3453.
(a) Vovk, M. V.; Sukach, V. A. Russ. J. Org. Chem.2005, 41, 1240. [Zh. Org. Khim.2005, 41, 1261.] (b) Sukach, V. A.; Bol'but, A. V.; Sinitsa, A. D.; Vovk, M. V. Synlett2006, 375.
Kushnir, O. V.; Sukach, V. A.; Vovk, M. V. J. Org. Pharm. Chem.2010, 8, 61. [Zh. Org. Farm. Khim.2010, 8, 61.]
Kushnir, O. V.; Vovk, M. V. Ukr. J. Chem.2010, 76, 45. [Ukr. Khim. Zh.2010, 76, 45.]
Kushnir, O. V.; Vovk, M. V. Russ. J. Org. Chem.2010, 46, 890. [Zh. Org. Khim.2010, 46, 894.]
Litvinchuk, M. B.; Bentya, A. V.; Slyvka, N. Y.; Vovk, M. V. J. Org. Pharm. Chem.2018, 64, 18. [Zh. Org. Farm. Khim.2018, 64, 18.]
(a) Steel, P. J.; Guard, J. A. M. Acta Crystallogr., Sect. C: Cryst. Struct. Commun.1994, C50, 1721. (b) Toplak, R.; Lah, N.; Volmajer, J.; Leban, I.; Acta Crystallogr., Sect. C: Cryst. Struct. Commun.2003, C59, o502.
Gorbatenko, V. I.; Samarai, L. I. Synthesis1980, 85.
Sinitsa, A. D.; Bonadyk, S. V.; Markovskii, L. N. J. Org. Chem. USSR1978, 14, 1030. [Zh. Org. Khim.1978, 14, 1107.]
Sheldrick, G. М. Acta Crystallogr., Sect. A: Found. Crystallogr.2008, A64, 112.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 101–107
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Litvinchuk, M.B., Bentya, A.V., Slyvka, N.Y. et al. A convenient method of synthesis of 8-acyl-2,3,6,7-tetrahydro-5Н-[1,3]thiazolo[3,2-c]pyrimidin-5-ones. Chem Heterocycl Comp 56, 101–107 (2020). https://doi.org/10.1007/s10593-020-02629-0
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DOI: https://doi.org/10.1007/s10593-020-02629-0