title: Iodine-mediated cascade cyclization of enediynes to iodinated benzo[a]carbazoles.
abstract: Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 1.2 equiv of iodine in CH(2)Cl(2) gave benzo[a]carbazoles (2) in good yields. Mechanistic studies showed this reaction must go through the haloindole (3) followed by iodonium ion catalyzed atom-transfer cyclization reaction to give the benzo[a]carbazoles.
authors: Department of Chemistry, National Sun Yat-sen University, Kaohsiung, Taiwan.
authors: Chin-Chau
authors: CC
authors: Chen
authors: Shyh-Chyun
authors: SC
authors: Yang
authors: Ming-Jung
authors: MJ
authors: Wu
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D053281:Enediynes / Q000737:chemistry*; D054879:Halogenation; D007211:Indoles / Q000737:chemistry; D007455:Iodine; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000814:Aniline Compounds; D002227:Carbazoles; D053281:Enediynes; D007211:Indoles; D007455:Iodine; C023650:aniline