title: Anionic N-Fries rearrangement of N-alkyl-2-iodo anilides induced by iodine-magnesium exchange: application for synthesis of strained 1,2,3-trisubstituted indoles.
abstract: A superior, mild, high-yielding one-pot process for rapid access to oxo anilides has been developed that involves three cascade reactions: iodine-magnesium exchange, regiospecific ortho N-Fries rearrangement, and in situ trapping of the formed aniline anion. Coupled with McMurry cyclization, the two-step process allows ready synthesis of strained 1,2,3-trisubstituted indoles regioselectively.
authors.affiliation: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, CT 06877, USA.
authors.forename: Fei
authors.initials: F
authors.lastname: Ding
authors.forename: Yongda
authors.initials: Y
authors.lastname: Zhang
authors.forename: Bo
authors.initials: B
authors.lastname: Qu
authors.forename: Guisheng
authors.initials: G
authors.lastname: Li
authors.forename: Vittorio
authors.initials: V
authors.lastname: Farina
authors.forename: Bruce Z
authors.initials: BZ
authors.lastname: Lu
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D000813:Anilides / Q000737:chemistry*; D000838:Anions; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*
chemical_list: D000813:Anilides; D000838:Anions; D007211:Indoles; D007455:Iodine; D008274:Magnesium