SYNTHESIS AND STUDY OF THE PROPERTIES OF CHALCONES BASED ON SUBSTITUTED ACETOPHENONES AND 3-FORMYLINDOLE
Rubrics: 1. CHEMISTRY
Authors:
1.
Bereznikovskiy filial Permskogo nacional'nogo issledovatel'skogo politehnicheskogo universiteta
Type:
Article
Pages:
from 11
to 14
Status:
Published
Received:
24.12.2025
Accepted:
25.12.2025
Published:
25.12.2025
Language:
Russian
Keywords:
CHALCONE, 3-NITROACETOPHENONE, 4-CHLORO-3-NITROACETOPHENONE, 3-FORMYLINDOLE, CONDENSATION, SPECTRAL METHODS OF RESEARCH
Abstract (English):
Chalcones have attracted the attention of scientists for many years due to their valuable physicochemical and biological properties. They are relatives of natural biologically active substances. Synthetic chalcones have found application in medicine, organic synthesis, agriculture and other fields. By their structure, chalcones belong to the class of α,b-unsaturated ketones. Several methods have been proposed for their preparation, the most common of which is based on the Claisen-Schmidt reaction. The presented work is devoted to the study of the reaction of 3-formylindole with substituted acetophenones and the study of the properties of the resulting chalcones. In the course of the study, a technique for the synthesis, isolation and purification of the reaction products was developed. The purity of the products was controlled by thin-layer chromatography. The chalcones under consideration are solid substances of yellow color with various shades. They are insoluble in water and soluble in polar organic solvents. The yields, melting points and Rf values were determined for the purified products. The structure of the synthesized chalcones was studied using IR Fourier spectroscopy (KBr) data. A number of common bands were isolated in the spectra, confirming their structural relationship, and distinctive features of the spectra were indicated. Based on the data obtained, it was established that the ethylene fragment in the chalcone molecules is in the trans-configuration. The spectra of chalcones in the ultraviolet and visible regions in isopropyl alcohol have intense absorption at about 310 nm and weak absorption at about 400 nm, attributed to absorptions involving p-electrons. This conclusion was made based on the analysis of the spectra measured in concentrated sulfuric acid. The results obtained are proposed for use in studying the properties of other chalcones.
Chalcones have attracted the attention of scientists for many years due to their valuable physicochemical and biological properties. They are relatives of natural biologically active substances. Synthetic chalcones have found application in medicine, organic synthesis, agriculture and other fields. By their structure, chalcones belong to the class of α,b-unsaturated ketones. Several methods have been proposed for their preparation, the most common of which is based on the Claisen-Schmidt reaction. The presented work is devoted to the study of the reaction of 3-formylindole with substituted acetophenones and the study of the properties of the resulting chalcones. In the course of the study, a technique for the synthesis, isolation and purification of the reaction products was developed. The purity of the products was controlled by thin-layer chromatography. The chalcones under consideration are solid substances of yellow color with various shades. They are insoluble in water and soluble in polar organic solvents. The yields, melting points and Rf values were determined for the purified products. The structure of the synthesized chalcones was studied using IR Fourier spectroscopy (KBr) data. A number of common bands were isolated in the spectra, confirming their structural relationship, and distinctive features of the spectra were indicated. Based on the data obtained, it was established that the ethylene fragment in the chalcone molecules is in the trans-configuration. The spectra of chalcones in the ultraviolet and visible regions in isopropyl alcohol have intense absorption at about 310 nm and weak absorption at about 400 nm, attributed to absorptions involving p-electrons. This conclusion was made based on the analysis of the spectra measured in concentrated sulfuric acid. The results obtained are proposed for use in studying the properties of other chalcones.
Keywords:
CHALCONE, 3-NITROACETOPHENONE, 4-CHLORO-3-NITROACETOPHENONE, 3-FORMYLINDOLE, CONDENSATION, SPECTRAL METHODS OF RESEARCH
CHALCONE, 3-NITROACETOPHENONE, 4-CHLORO-3-NITROACETOPHENONE, 3-FORMYLINDOLE, CONDENSATION, SPECTRAL METHODS OF RESEARCH
