Metal-Free Radical Haloazidation of Benzene-Tethered 1,7-Enynes Leading to Polyfunctionalized 3,4-Dihydroquinolin-2(1H)-ones

Ai-Fang Wang, Yi-Long Zhu, Shu-Liang Wang, Wen-Juan Hao, Guigen Li, Shu-Jiang Tu, Bo Jiang

Research output: Contribution to journalArticle

Abstract

A new cascade three-component haloazidation of benzene-tethered 1,7-enynes for the formation of biologically interesting azidylated 3,4-dihydroquinolin-2(1H)-ones has been achieved under mild and metal-free conditions using TMSN3 as a N-3 source and NIS (or NBS or NCS) as a halogen source. The reaction pathway involves in situ-generated azidyl radical-triggered alpha,beta-conjugated addition/6-exo-dig cyclization/radical coupling sequence, resulting in successive multiple bond-forming events, including carbon-nitrogen, carbon-carbon, and carbon-halogen bonds to rapidly construct complex heterocyclic molecules. Furthermore, the resulting products would be useful building blocks in the discovery of lead compounds and other biologically interesting N-3-containing heterocycles.
Original languageEnglish
Pages (from-to)1099-1105
JournalJournal of Organic Chemistry
StatePublished - Feb 2016

Fingerprint Dive into the research topics of 'Metal-Free Radical Haloazidation of Benzene-Tethered 1,7-Enynes Leading to Polyfunctionalized 3,4-Dihydroquinolin-2(1H)-ones'. Together they form a unique fingerprint.

Cite this