title: Metal-Free Radical Haloazidation of Benzene-Tethered 1,7-Enynes Leading to Polyfunctionalized 3,4-Dihydroquinolin-2(1H)-ones.
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.
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, P. R. China.
authors.forename: Ai-Fang
authors.initials: AF
authors.lastname: Wang
authors.affiliation: Biotechnology and Pharmaceutical Engineering, Nanjing Tech University , Nanjing 210009, P. R. China.
authors.forename: Yi-Long
authors.initials: YL
authors.lastname: Zhu
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, P. R. China.
authors.forename: Shu-Liang
authors.initials: SL
authors.lastname: Wang
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, P. R. China.
authors.forename: Wen-Juan
authors.initials: WJ
authors.lastname: Hao
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University , Lubbock, Texas 79409-1061, United States .
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, P. R. China.
authors.forename: Shu-Jiang
authors.initials: SJ
authors.lastname: Tu
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, P. R. China.
authors.forename: Bo
authors.initials: B
authors.lastname: Jiang
mesh_terms: D001386:Azides / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D001686:Biological Phenomena; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001386:Azides; D005609:Free Radicals; D008670:Metals; D015363:Quinolones; C588100:dihydroquinolin-2(1H)-one; D002244:Carbon; D001554:Benzene; D009584:Nitrogen