title: Synthesis of nitrogen-containing fused-polycyclic compounds from tyramine derivatives using phenol dearomatization and cascade cyclization.
abstract: We developed a novel method of synthesizing nitrogen-containing fused-polycyclic compounds using tyramine derivatives as substrates. The method is based on the dearomatization of phenols via an intramolecular ipso-Friedel-Crafts allenylation and sequential bond-forming-cleavage reactions initiated by the construction of an indole skeleton. Structurally diverse fused-heterocycles were produced in reaction sequences requiring only a few steps.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan. y-hamada@faculty.chiba-u.jp.
authors.forename: Takuya
authors.initials: T
authors.lastname: Yokosaka
authors.forename: Tetsuhiro
authors.initials: T
authors.lastname: Nemoto
authors.forename: Hiroki
authors.initials: H
authors.lastname: Nakayama
authors.forename: Naoki
authors.initials: N
authors.lastname: Shiga
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Hamada
mesh_terms: D002384:Catalysis; D003500:Cyclization; D058116:Lewis Acids / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D019800:Phenol / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry; D014439:Tyramine / Q000737:chemistry*
chemical_list: D058116:Lewis Acids; D011083:Polycyclic Compounds; D019800:Phenol; D014269:Trifluoroacetic Acid; D009584:Nitrogen; D014439:Tyramine