期刊
JOURNAL OF CHEMICAL RESEARCH
卷 45, 期 1-2, 页码 159-165出版社
SAGE PUBLICATIONS LTD
DOI: 10.1177/1747519820932789
关键词
1; 3-dipolar cycloaddition; antioxidant activity; click chemistry; condensation reaction; O-alkylation; triazolated derivatives
资金
- TUBITAK-BIDEB [2221]
In this study, a series of novel 4-O-alkyltriazolylphenolic derivatives and chalcones were synthesized using click reaction and Claisen-Schmidt method, and the antioxidant activity of the newly synthesized compounds was evaluated.
A series of novel 4-O-alkyltriazolylphenolic derivatives is first synthesized with good to excellent yields via the click reaction of 3-methoxy-4-O-propargylbenzaldehyde or 3-allyl-4-O-propargylacetophenone and aromatic azide derivatives. Next, the chalcones are prepared via the Claisen-Schmidt method from 4-O-alkylphenylketone derivatives in the presence of the corresponding (hetero)aromatic aldehydes as electrophiles. The structures of the newly synthesized compounds are confirmed from their infrared, nuclear magnetic resonance spectral data, and by elemental analysis. The main advantages of this procedure are the simplicity of the reaction conditions, easily available starting materials, and simple work-up. The antioxidant activity of several of the products is determined using the DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) radical scavenging assay. 4-O-propargylvanillin (IC50 = 14.54 mu g/mL) had moderate antioxidant activity.
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