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Issue 39, 2018
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Organic amine-mediated free-radical carbocyclization reactions of 2,2,2-trihalogeno-substituted N-(2-alkynylphenyl)acetamides

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Abstract

An efficient method for the synthesis of 3-halogeno-substituted 4-benzoylquinolin-2-(1H)-ones from N-(2-alkynylphenyl)-substituted trihaloacetamides has been developed, in which organic amines (TNPA and DIEA) act as the electron donors. In this carbocyclization reaction, a new C–C bond formation occurred regioselectively via a 6-exo-dig radical cyclization. A variety of useful functional groups are compatible with the reaction conditions. In this process, readily removable organic amines were employed and no heavy metal catalysts were required.

Graphical abstract: Organic amine-mediated free-radical carbocyclization reactions of 2,2,2-trihalogeno-substituted N-(2-alkynylphenyl)acetamides

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Publication details

The article was received on 02 Aug 2018, accepted on 18 Sep 2018 and first published on 18 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01870G
Citation: Org. Biomol. Chem., 2018,16, 7265-7273
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    Organic amine-mediated free-radical carbocyclization reactions of 2,2,2-trihalogeno-substituted N-(2-alkynylphenyl)acetamides

    T. Chuang and C. Chuang, Org. Biomol. Chem., 2018, 16, 7265
    DOI: 10.1039/C8OB01870G

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