title: Smooth isoindolinone formation from isopropyl carbamates via Bischler-Napieralski-type cyclization.
abstract: Isopropyl carbamates derived from benzylamines provide isoindolinones by treatment with phosphorus pentoxide at room temperature. Utility of this Bischler-Napieralski-type cyclization and a new mechanism involving a carbamoyl cation for rationalization of this smooth conversion are discussed.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Adachi
authors.forename: Masao
authors.initials: M
authors.lastname: Onozuka
authors.forename: Yuko
authors.initials: Y
authors.lastname: Yoshida
authors.forename: Mitsuaki
authors.initials: M
authors.lastname: Ide
authors.forename: Yoko
authors.initials: Y
authors.lastname: Saikawa
authors.forename: Masaya
authors.initials: M
authors.lastname: Nakata
mesh_terms: D019840:2-Propanol / Q000737:chemistry; D001596:Benzylamines / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D003500:Cyclization; D004952:Esters; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017553:Phosphorus Compounds / Q000737:chemistry; D013696:Temperature
chemical_list: D001596:Benzylamines; D002219:Carbamates; D004952:Esters; D007211:Indoles; D017553:Phosphorus Compounds; C012500:phosphorus pentoxide; D019840:2-Propanol