期刊
JOURNAL OF MOLECULAR STRUCTURE
卷 1241, 期 -, 页码 -出版社
ELSEVIER
DOI: 10.1016/j.molstruc.2021.130629
关键词
Alkylation; 5-(4-hydroxybenzylidene)-thiazolidine-2,4-dione; Alkyl halide; Alkaline; Spectroscopy
资金
- Iuliu Hatieganu University of Medicine and Pharmacy, Cluj-Napoca, Romania [PCD 7690/68/15.04.2016, 5200/59/01.03.2017, 3067/4/01.02.2018, 1529/39/18.01.2019]
- Core Program (Program Nucleu) [PN 19 35 02 01]
The study discusses the importance of thiazolidine-2,4-dione in medicinal chemistry and the synthesis of its derivatives through N-alkylation and O-alkylation reactions. Experimental results indicate the formation of N-alkylated derivatives under reaction conditions, providing a new pathway for the synthesis of biologically active compounds.
Thiazolidine-2,4-dione represents a key heterocyclic core in medicinal chemistry because it has the ability to bind to a wide variety of protein targets and has been intensively studied for developing bioactive multitargeting agents. The N-alkylation of imides and O-alkylation of phenols are important reactions frequently used in the synthesis of biologically active compounds, like the thiazolidine-2,4-dione derivatives. Based on literature data, by treating (Z)-5-(4-hydroxybenzylidene)-thiazolidine-2,4-dione with alkyl halides in a 1:1 molar ratio, either O-alkylation or N-alkylation reactions can take place. Six (Z)-5-(4-hydroxybenzylidene)-thiazolidine-2,4-dione derivatives were synthesized by alkylating (Z)-5-(4-hydroxybenzylidene)-thiazolidine-2,4-dione with aliphatic halogenated derivatives in alkaline environment, using a 1:1 molar ratio and then were physically and spectrally analyzed. The spectral data and the results obtained from the theoretical evaluation of the parent compound's acidity support the formation of N-alkylated derivatives in the reaction conditions. (C) 2021 Elsevier B.V. All rights reserved.
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