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Issue 34, 2013
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Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation

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Abstract

Diverse reactivity by coupling of substituted anilines with ethyl trifluoropyruvate was developed under microwave irradiation without catalysts to generate 3-trifluoromethyl-3-hydroxy oxindoles, aromatic hydroxy trifluoromethyl esters, and 1,2-dicarbonyl compounds in a fast and efficient manner. The plausible mechanism for obtaining different products was proposed. Furthermore, the anti-HIV activity of aromatic hydroxy trifluoromethyl esters was first reported. The best inhibitory activity against wild-type HIV-1 IIIB was exemplified by trifluoromethyloxindole 3q with an IC50 = 5.8 μM, which also displayed potential activity against Y181C mutant virus with an IC50 = 7.5 μM. More significantly, the activities of oxindoles 3q and 3r to inhibit K103N/Y181C double mutant HIV-1 reverse transcriptase (RT) are probably similar to that of the second-generation nonnucleoside inhibitor HBY 097 by docking calculation.

Graphical abstract: Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation

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Publication details

The article was received on 02 Apr 2013, accepted on 18 Jun 2013 and first published on 19 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB40650D
Citation: Org. Biomol. Chem., 2013,11, 5621-5633
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    Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation

    C. Zhang, D. Zhuang, J. Li, S. Chen, X. Du, J. Wang, J. Li, B. Jiang and J. Yao, Org. Biomol. Chem., 2013, 11, 5621
    DOI: 10.1039/C3OB40650D

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