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Issue 48, 2018
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Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones

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Abstract

An efficient method for the synthesis of 4-trifluoromethyl 2-pyrones through the Brønsted base-catalyzed Pechmann-type reaction of cyclic 1,3-diones with ethyl 4,4,4-trifluoroacetoacetate is described. In the presence of 2-dimethylamino pyridine (2-DMAP) as a catalyst, the resulting 4-trifluoromethyl 2-pyrones are formed in good to excellent yields. Additionally, the reaction also provides 4-trifluoromethyl 2-pyridones by using the easily available NH4OAc as a source of NH3.

Graphical abstract: Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones

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Publication details

The article was received on 31 Oct 2018, accepted on 27 Nov 2018 and first published on 27 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02701C
Citation: Org. Biomol. Chem., 2018,16, 9440-9445
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    Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones

    W. Yan, R. Wang, T. Zhang, H. Deng, J. Chen, W. Wu and Z. Weng, Org. Biomol. Chem., 2018, 16, 9440
    DOI: 10.1039/C8OB02701C

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