Organic Letters
Organic Letters
5 years ago

Copper-Catalyzed Cascade Cyclization of 1,7-Enynes toward Trifluoromethyl-Substituted 1′H-Spiro[azirine-2,4′-quinolin]-2′(3′H)-ones

Copper-Catalyzed Cascade Cyclization of 1,7-Enynes toward Trifluoromethyl-Substituted 1′H-Spiro[azirine-2,4′-quinolin]-2′(3′H)-ones
Bing Han, Wei Yu, Fei Chen, Qiang Meng
A novel method for the synthesis of trifluoromethyl-containing 1′H-spiro[azirine-2,4′-quinolin]-2′(3′H)-ones by a CF3-radical-triggered tandem reaction of benzene-linked 1,7-enynes is described. This protocol utilizes 1-trifluoromethyl-1,2-benziodoxole as the trifluoromethylating reagent and TMSN3 as the aminating reagent. By this method, various potentially bioactive trifluoromethylated 1′H-spiro[azirine-2,4′-quinolin]-2′(3′H)-ones were facilely synthesized via a radical cascade process.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02453

DOI: 10.1021/acs.orglett.7b02453

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