title: Coupling and cyclization of o-iodoanilines and propargylic bromides via allenes: an efficient entry to indomethacin.
abstract: A sequential allene synthesis and cyclization has been realized in a one-pot manner. A Pd(0)-catalyzed one-pot reaction of N-Ts or -Ms 2-iodoanilines and propargylic bromides afforded indoles with pharmaceutical importance highly efficiently with diversity via sequential carbon-carbon bond coupling forming allenes and azapalladation. With this newly established methodology, an efficient approach to indomethacin, an anti-inflammatory drug (NSAID), has been accomplished.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
authors.forename: Can
authors.initials: C
authors.lastname: Zhu
authors.forename: Shengming
authors.initials: S
authors.lastname: Ma
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007213:Indomethacin / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000814:Aniline Compounds; D000893:Anti-Inflammatory Agents; D001965:Bromides; D010165:Palladium; C075715:3-iodoaniline; D010293:Pargyline; C458239:propargyl bromide; D007213:Indomethacin