Iranian Journal of Chemistry

Iranian Journal of Chemistry

The application of FeCl3 in the synthesis of α-ketothioamides and study of the antibacterial effect of these compounds against Escherichia coli bacteria

Document Type : Original Article

Authors
Sadegh Rahmati 1
Arash Ghaderi 2
Sajedeh Ameri Siahooei 3
Fatemeh Sedaghat 4
Morteza Yousefzadi 5
1 Payame noor univer
2 Department of Chemistry, College of Sciences, University of Hormozgan, Bandar Abbas, Iran
3 Department of Chemistry, College of Sciences, University of Hormozgan
4 Department of Marine Biology, Faculty of Marine Sciences and Technology, University of Hormozgan, Bandar Abbas, Iran.
5 Department of Biology, Faculty of Sciences, University of Qom, Qom, Iran
10.22036/cr.2023.387700.1209
Abstract
In this project, a mild and efficient procedure for the synthesis of α-ketothioamide derivatives is described. N,N-dimethylformamide (DMF) is mainly used as a polar solvent in organic reactions, but it can also be used as a source of various functional groups. In this study, N,N-dimethylformamide compound is used as an amino group source for the synthesis of α-ketothioamide compounds. These compounds is synthesized from the ketone as substance with a new and simple method. In this project, we used iron (Ⅲ) chloride as efficient catalyst for synthesis of α-ketothioamide. Also, the synthesis of α-ketothioamide is carried out in the presence of oxidant and octasulfur. The use of imidazole as an activator, plays an important role in these transformations. All the synthesized products have been fully identified by 1HNMR and 13CNMR spectroscopic methods. At the end of this project, we studied the antibacterial effect of new synthesized compounds against Escherichia coli bacteria.

Graphical Abstract

The application of FeCl3 in the synthesis of α-ketothioamides and study of the antibacterial effect of these compounds against Escherichia coli bacteria
Keywords
Aryl methyl ketone
N N-dimethylformamide
N N-dimethylamine
Iron (Ⅲ) chloride
α-ketothioamide
Subjects
[1] M. M. Heravi, M. Ghavidel, L. Mohammadkhani, RSC Adv., 8 (2018) 27832.
[2] S. Yamaguchi, H. Shinokubo, A. Osuka, Inorg. Chem., 48 (2009) 795.
[3] P. Supsana, T. Liaskopoulos, P. G. Tsounggas, G. Varvounis, Synlett., 17 (2007) 2671.
[4] I. Pastoriza-Santos, L. M. Liz-Marzan, Nano Lett., 2 (2002) 903.
[5] Y. Liu, G. He, K. Chen, Y. Jin, H. Zhu, Eur. J. Org. Chem., (2011) 5323.
[6] W. Mai, H. Wang, Z. Li, J. Yuan, Y. Xiao, L. Yang, P. Mao, L. Qu, Chem. Commun., 48 (2012) 10117.
[7] W. Liu, C. Chen, P. Zhou, Chemistry Select, 2 (2017) 5532.
[8] W. Yuan, C. H. Wong, J. Z. Haeggstrom, A. Wetterholm, B. Samuelsson, J. Am. Chem. Soc., 114
(1992) 6552.
[9] Q. Spillier, S. Ravez, J. Unterlass, C. Corbet, C. Degavre, O. Feron, R. Frédérick, Pharmaceuticals, 13
(2020) 20.
[10] A. Muthukumar, S. Sangeetha, G. Sekar, Org. Biomol. Chem., 16 (2018) 7068.
[11] M. Suchy, A. A. H. Elmehriki, R. H. E. Hudson, Org. Lett., 13 (2011) 3952.
[12] J. C. Powers, R. Seidnerl, T. G. Parsons, Tetrahedron Lett., 6 (1965) 1713.
[13] Q. Zhao, T. Miao, X. Zhang, W. Zhou, L. Wang, Org. Biomol. Chem., 11 (2013) 1867.
[14] (a) M. Zhou, Q. Song, Synthesis, 46 (2014)1853.;  (b) W. Liu, S. Xu, C. Chen, Z. Zhu, Chemistry Select, 1 (2016) 612.
[15] J. M. Desper, R. Breslow, J. Am. Chem. Soc., 116 (1994) 12081.
[16] Y. Zhang, N. G. Pavlopoulos, T. S. Kleine, M. Karayilan, R. S. Glass, K. Char, J. Pyun, J. Polym. Sci.
Part A Polym. Chem., 57 (2018) 7.
[17] J. Wang, J. T. Hou, J. Wen, J. Zhang, X. Q. Yu, Chem. Commun., 47 (2011) 3652.
[18] I. Radfar, S. Abbasi, M. Kazemi Miraki, E. Yazdani, M. Karimi, A. Heydari, Chemistry Selec., 3
(2018) 3265.
 [21] S. Jadhav, R. Shah, M. Bhave, E. A. Palombo,  Food Control, 29 (2013) 125.
[22] F. Abdollahi, A. Ghaderi, J. Chin. Chem. Soc., 70 (2023) 949.
Iranian Journal of Chemistry
Volume 6, Issue 2 - Serial Number 11
December 2023
Pages 189-199

  • Receive Date 14 March 2023
  • Revise Date 07 July 2023
  • Accept Date 04 October 2023