title: Direct inter- and intramolecular addition of amides to arylalkenes promoted by KOt-Bu/DMF.
abstract: Direct addition of tetrahydroisoquinoline derived amides to arylalkenes has been achieved in the presence of KOt-Bu/DMF. Both intermolecular and intramolecular reactions could occur in good yields. α-Amido alkyl radicals are proposed to be generated under the reaction conditions. The reaction is efficient for the synthesis of seven-membered nitrogen heterocycles. A homoprotoberberine was prepared conveniently via this method.
authors.affiliation: Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, China.
authors.forename: Wei-juan
authors.initials: WJ
authors.lastname: Wang
authors.forename: Xu
authors.initials: X
authors.lastname: Zhao
authors.forename: Lang
authors.initials: L
authors.lastname: Tong
authors.forename: Jia-hua
authors.initials: JH
authors.lastname: Chen
authors.forename: Xue-jing
authors.initials: XJ
authors.lastname: Zhang
authors.forename: Ming
authors.initials: M
authors.lastname: Yan
mesh_terms: D000577:Amides / Q000737:chemistry*; D000440:Butanols / Q000737:chemistry*; D002384:Catalysis; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000595360:(3,4-dihydroisoquinolin-2(1H)-yl)(1-methyl-1H-pyrrol-2-yl)methanone; D000577:Amides; D000440:Butanols; D003516:Cycloparaffins; D006571:Heterocyclic Compounds; D007546:Isoquinolines; D011758:Pyrroles; C077664:tert-butoxide, potassium; D009584:Nitrogen