title: Synthesis of substituted indoline and carbazole by benzyne-mediated cyclization-functionalization.
abstract: A benzyne-mediated synthesis of substituted indolines and carbazoles was developed. The reaction includes generation of benzyne using Mg(TMP)2·2LiCl as a base, cyclization, and trapping the resulting organomagnesium intermediate with an electrophile to provide a series of substituted indolines and carbazoles in a regiospecific manner. This was applied to a concise five-pot total synthesis of heptaphylline.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Toshiharu
authors.initials: T
authors.lastname: Noji
authors.forename: Hideto
authors.initials: H
authors.lastname: Fujiwara
authors.forename: Kentaro
authors.initials: K
authors.lastname: Okano
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Tokuyama
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D001555:Benzene Derivatives; D002227:Carbazoles; D007211:Indoles; C524146:benzyne; C557424:heptaphylline; C057812:indoline