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Synthesis of 2-Oxo(thio)-N,4-diaryl-1,2,3,4-tetrahydropyrimidine-5-carbothioamides

Olena Maiboroda and Nathaliia Simurova
Affiliation: 
National University of Food Technologies, 68, Volodymyrska St., 01601 Kyiv-33, Ukraine
DOI: 
https://doi.org/10.23939/chcht10.03.279
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Keywords:

Abstract: 
It was found that 2-acylthioacetamides enter Biginelli reaction with aromatic aldehydes and urea /thiourea forming 2-oxo(thio)-N,4-diaryl-1,2,3,4-tetrahydropyrimidine-5-carbothioamides. Under the influence of K3[Fe(CN)6] in alkaline environment, the expected 2-oxo(thio)-N,4-diaryl-5-(benzothiazole-2'-yl)-1,2,3,4-tetrahydropyrimidines were not been received while 2-oxo(thio)-N,4-diaryl-1,2,3,4-tetrahydropyrimidine-5-carbamides were the products of interaction.
References: 

[1] Britsun V.: 2-Funkcializirovannye Metilenactivnye Tioacetamidy. Komprint, Kyiv 2012.

[2] Britsun V., Esipenko A. and Lozinskii M.: Chem. Heterocycl. Compd., 2008, 44, 1429.
https://doi.org/10.1007/s10593-009-0214-x

[3] Li M., Zuo Z., Wen L. and Wang S.: J. Comb. Chem., 2008, 10, 436.
https://doi.org/10.1021/cc700194b

[4] Wen L.-R., Ji C., Li M. and Xie H.: Tetrahedron, 2009, 65, 1287.
https://doi.org/10.1016/j.tet.2008.12.057

[5] Saini A., Kumar S. and Sandhu J.: J. Indian Chem. Soc., 2007, 84, 959.

[6] Bhavya K., Purohit M. and Pujar G.: Indian Drugs, 2011, 48, 7.

[7] Kappe C.: Qsar Comb. Sci., 2003, 22, 630.
https://doi.org/10.1002/qsar.200320001

[8] Schneider P., Stutz K., Kasper L. et al.: Pharmaceuticals, 2011, 4, 1236.
https://doi.org/10.3390/ph4091236

[9] Vdovina S. and Mamedov V.: Russ. Chem. Rev., 2008, 77, 1017.
https://doi.org/10.1070/RC2008v077n12ABEH003894

[10] Suresh Sandhu J.: ARKIVOC, 2012, 1, 66.

[11] Shujang T., Fang F., Chunbao M. et al.: Tetrahedron Lett., 2003, 44, 6153.
https://doi.org/10.1016/S0040-4039(03)01466-7

[12] Cronyn M. and Nakagawa T.: J. Am. Chem. Soc., 1952, 74, 3693.
https://doi.org/10.1021/ja01134a506

[13] Britsun V., Borisevich A., Samoilenko L. et al.: Russ. Chem. Bull., 2005, 54, 770.
https://doi.org/10.1007/s11172-005-0318-0

[14] Inamoto K., Nozawa K. and Kondo Y.: Synlett., 2012, 23, 1678.
https://doi.org/10.1055/s-0031-1291164

[15] Huang P., Liang Y. and Zhang R.: Austr. J. Chem., 2012, 65, 121.
https://doi.org/10.1071/CH11330

[16] Downer-Riley N. and Jackson Y.: Tetrahedron, 2008, 64, 7741.
https://doi.org/10.1016/j.tet.2008.06.023

[17] Movassagh B., Lakouraj M. and Gholami A.: Phosphorus, Sulfur Silicon Relat. Elem., 2003, 178, 1943.
https://doi.org/10.1080/10426500390228620

[18] Jorgensen K., Ghattas A. and Lawesson S.: Tetrahedron, 1982, 38, 1163.
https://doi.org/10.1016/0040-4020(82)85099-0

[19] Jorgensen K., Wassimy M. and Lawesson S.: Tetrahedron, 1983, 39, 469.
https://doi.org/10.1016/S0040-4020(01)88548-3