Journal
SYNTHESIS-STUTTGART
Volume 47, Issue 24, Pages 3881-3890Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1560322
Keywords
o-aminoacetophenones; aldehydes; silver(I) triflate; condensation; quinolinones; antioxidants
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Funding
- Nano Material Technology Development Program of the Korean National Research Foundation (NRF) - Korean Ministry of Education, Science, and Technology [2012-049675]
- Korean National Research Foundation (NRF) grant - Korean government (MSIP) [NRF-2014R1A2A1A11052391]
- Priority Research Centers Program [2014R1A6A1031189]
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Biologically interesting 2-aryl-2,3-dihydroquinolin-4(1H)-ones were synthesized using a mild and efficient one-pot procedure starting from o-aminoacetophenones and aromatic aldehydes in the presence of silver(I) triflate. This synthetic protocol provides rapid access to a variety of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. This technique has several advantages, such as the use of easily available starting materials, the efficiency of the catalyst, a simple operation, and tolerance of a wide range of functionality in the aldehydes. Screening of the synthesized compounds for their antioxidant properties revealed that two compounds (with EC50 = 15.42 M and 15.16 M) exhibit a potent free-radical scavenging ability towards TEAC free radicals compared to the standard, Trolox.
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