Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 3, Pages 1099-1105Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02655
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Funding
- NSFC [21232004, 21332005, 21272095, 21472071]
- PAPD of Jiangsu Higher Education Institutions
- Robert A. Welch Foundation (USA) [D-1361]
- NIH (USA) [R33DA031860]
- Outstanding Youth Fund of JSNU [YQ2015003]
- NSF of Jiangsu Province [BK20151163]
- Open Foundation of Jiangsu Key Laboratory [K201505]
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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.
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