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Synthesis and antioxidant activities of novel N ‐aryl (and N ‐alkyl) γ‐ and δ‐imino esters and ketimines
Author(s) -
Hasdemir Belma,
Yaşa Hasniye,
Akkamış Yağmur
Publication year - 2019
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201800126
Subject(s) - chemistry , butylated hydroxytoluene , butylated hydroxyanisole , antioxidant , alkyl , dpph , ascorbic acid , aryl , organic chemistry , carbon 13 nmr , proton nmr , medicinal chemistry , nuclear chemistry , food science
Novel N ‐aryl (and N ‐alkyl) γ‐ and δ‐imino esters 2a–g ( 3a–g ) and N ‐aryl (and N ‐alkyl) ketimines 2h–j ( 3h–j ) were synthesized in high yields (80–99%) from their corresponding γ‐ and δ‐keto esters and ketones in this study. The structures of the synthesized compounds were clarified by Fourier transform infrared (FT‐IR), NMR ( 1 H and 13 C), mass spectrometry, and elemental analyses. Isomerizations [ E / Z ] were also determined by their 1 H NMR spectra. The free‐radical scavenging activity of imines was evaluated using the 1,1‐diphenyl‐2‐picryl‐hydrazyl (DPPH) method. The relationships between the structure and antioxidant activity of these compounds are discussed. Among these compounds, 2a–c (at the concentration 1000 μg/mL) exhibit high antioxidant activity similar to those of the standards (butylated hydroxyanisole [ BHA], butylated hydroxytoluene [ BHT], and ascorbic acid).