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

47 Scopus citations

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 N3 source and NIS (or NBS or NCS) as a halogen source. The reaction pathway involves in situ-generated azidyl radical-triggered α,β-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 N3-containing heterocycles.

Original languageEnglish
Pages (from-to)1099-1105
Number of pages7
JournalJournal of Organic Chemistry
Volume81
Issue number3
DOIs
StatePublished - Feb 5 2016

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