Open AccessSynthesis and structure of thiourea derivatives of functionally substituted pyridines
Author(s) -
О. А. Нуркенов,
С. Д. Фазылов,
Т. М. Сейлханов,
Ж. С. Нурмаганбетов,
А. М. Газалиев,
G.Zh. Karipova
Publication year - 2021
Publication title -
ķaraġandy universitetìnìn̦ habaršysy. himiâ seriâsy
Language(s) - English
Resource type - Journals
eISSN - 2663-4872
pISSN - 2518-718X
DOI - 10.31489/2021ch1/4-11
Subject(s) - chemistry , thiourea , moiety , heteronuclear molecule , pyridine , potassium thiocyanate , chemical shift , carbon 13 nmr , proton nmr , chloride , acetone , stereochemistry , thiocyanate , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry
The article presents data on the synthesis and study of the structure of thiourea derivatives of functionally substituted pyridines. New thiourea derivatives containing a pharmacologically active pyridine moiety in their structure were obtained. As the starting synton, 2-amino-5-bromopyridine, 2-amino-3-hydroxypyridine and 2-aminomethylpyridine were selected. It was shown that the interaction of 2-amino-5-bromopyridine, 2-amino-3-hydroxypyridine and 2-aminomethylpyridine with ethyl and phenylisothiocyanates in ethanol leads to the formation of the corresponding pyridine-containing thioureas. The synthesis of the initial isothiocyanates was carriedout in situ from the corresponding acidic chlorides (benzoyl chloride and p-brombenzoyl chloride) by heating them with potassium thiocyanate in acetone. The structure of the synthe-sized compounds was studied by 1H and 13C NMR spectroscopy, as well as by the data of two-dimensional spectra of COSY (1H-1H) and HMQC (1H-13C). The values of chemical shifts, multiplicity, and integrated in-tensity of 1H and 13C signals in one-dimensional NMR spectra were determined. Using spectra in the formats COSY (1Н-1Н) and HMQC (1Н-13С), homo-and heteronuclear interactions were established, confirming the structure of the studied compounds.