title: Facile preparation of indoles and 1,2-benzothiazine 1,1-dioxides: nucleophilic addition of sulfonamides to bromoacetylenes and subsequent palladium-catalyzed cyclization.
abstract: Bromine as a double agent: The bromine atom in 1-bromo-1-alkynes works as an electron-withdrawing group to effect the nucleophilic addition of sulfonamides. It again plays a pivotal role in the palladium-catalyzed cyclization of the resultant (Z)-2-(sulfonylamino)-1-bromoalkenes into nitrogen heterocycles (see scheme).
authors.affiliation: Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
authors.forename: Masahito
authors.initials: M
authors.lastname: Yamagishi
authors.forename: Ken
authors.initials: K
authors.lastname: Nishigai
authors.forename: Azusa
authors.initials: A
authors.lastname: Ishii
authors.forename: Takeshi
authors.initials: T
authors.lastname: Hata
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Urabe
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010087:Oxides / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D013843:Thiazines / Q000737:chemistry*
chemical_list: D000480:Alkynes; D006571:Heterocyclic Compounds; D007211:Indoles; D010087:Oxides; D013449:Sulfonamides; D013843:Thiazines; D010165:Palladium; D001966:Bromine