2-Iminothiazolidin-4-one Derivatives: Synthesis, Characterization, and Quantum-Chemical Calculations

被引：0
作者：
R. B. Nadr [1 ]
Y. H. Azeez [2 ]
R. A. Omer [1 ]
K. M. Ahmed [3 ]
R. O. Kareem [4 ]
机构：
[1] Department of Chemistry, Faculty of Science and Health, Koya University, Koya KOY45, Kurdistan Region
[2] Physics Department, College of Science, University of Halabja, Halabja
[3] Department of Pharmacy, College of Pharmacy, Knowledge University, Erbil
[4] Department of Chemistry, College of Education, University of Garmian, Kalar
来源：
Russian Journal of Organic Chemistry | 2025年 / 61卷 / 2期
关键词：
2-minothiazolidin-4-one; HOMO; IR; LUMO; MEP; NBO; NCL; NMR;
D O I：
10.1134/S1070428023603035
中图分类号：
学科分类号：
摘要：
Abstract: This study presents the synthesis and spectroscopic and quantum chemical calculations of novel 2-imino-thiazolidin-4-one derivatives. The synthetic strategy was divided into three key stages. Initially, 2-amino-4-(substituted phenyl)-1,3-thiazoles were obtained through the reaction of thiourea with substituted acetophenone in the presence of iodine. At the next step, the resulting heterocyclic amines were treated with chloroacetyl chloride in benzene to obtain 2-chloroacetamido-4-(substituted phenyl)-1,3-thiazole. Finally, the latter was subjected to heteroannulation with potassium thiocyanate to form the target 2-imino-3-[4-(substituted phenyl)-1,3-thiazol-2-yl]thiazolidin-4-ones. The molecular structure of the five newly synthesized compounds was elucidated by IR and 1H and 13C NMR spectroscopy. A variety of quantum-chemical methods, including reduced density gradient (RDG) analysis, natural bond orbital (NBO) analysis, and analysis of potential energy maps (PEMs), HOMO–LUMO energy gaps, topological, and thermodynamic parameters were employed to study the structural and electronic properties and reactivity of the products, with potential implications for chemical and biological applications. © Pleiades Publishing, Ltd. 2025.
引用
收藏
页码：292 / 311
页数：19
相关论文
共 44 条
  • [1] Naresh K., Nidhi G., Anticancer Agents Med. Chem, 22, (2022)
  • [2] Konstantinos L., Maria F., Athina G., Molecules, 23, (2018)
  • [3] Singh S.P., Parmar S.S., Raman K., Stenberg V.I., Chem. Rev, 81, (1981)
  • [4] Jie H., Yi W., Xiaoyan W., Xixi W., Gaozhi C., Gaozhong C., Xueqian S., Xiuhua Z., Qinqin T., Guang L., Xiaokun L., Eur. J. Med. Chem, 64, (2013)
  • [5] Patel D., Patel R., Kumari P., Patel N., Med. Chem. Res, 21, (2012)
  • [6] Chawla P., Singh R., Saraf K.S., Med. Chem. Res, 21, (2012)
  • [7] Matiichuk V., Obushak N., Tsyalkovskii V., Russ. J. Org. Chem, 41, (2005)
  • [8] Liu H.-L., Li Z., Anthonsen T., Molecules, 5, (2000)
  • [9] Blanchet J., Zhu J., Tetrahedron Lett, 45, (2004)
  • [10] Aziz H.J., Salih K.M., J. Pure Appl. Sci, 22, (2010)
12345