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Org Biomol Chem. 2018 Oct 10;16(39):7265-7273. doi: 10.1039/c8ob01870g.

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

Author information

1
Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 70101, Republic of China. cpchuang@mail.ncku.edu.tw.

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.

PMID:
30259031
DOI:
10.1039/c8ob01870g

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