title: Photochemical intramolecular cyclization of o-alkynylaryl isocyanides with organic dichalcogenides leading to 2,4-bischalcogenated quinolines.
abstract: When a mixture of o-alkynylaryl isocyanides and organic dichalcogenides such as diselenides or ditellurides was irradiated with light of wavelength over 300 or 400 nm, the intramolecular cyclization of the isocyanides took place to afford the corresponding 2,4-bischalcogenated quinolines selectively. The photochemical cyclization of 2-(phenylethynyl)phenyl isocyanide could also proceed in the presence of hydrogen transfer reagents such as tris(trimethylsilyl)silane, tributylgermyl hydride, alkanethiols, and benzeneselenol, providing the corresponding 3-phenylquinoline as the result of 2,4-dihydrogenation.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka, Japan.
authors.forename: Takenori
authors.initials: T
authors.lastname: Mitamura
authors.forename: Kimiyo
authors.initials: K
authors.lastname: Iwata
authors.forename: Akihiro
authors.initials: A
authors.lastname: Nomoto
authors.forename: Akiya
authors.initials: A
authors.lastname: Ogawa
mesh_terms: D018011:Chalcogens / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D055668:Photochemical Processes; D011804:Quinolines / Q000737:chemistry*
chemical_list: D018011:Chalcogens; D003486:Cyanides; D011804:Quinolines; D006859:Hydrogen