title: Construction of azacycles based on endo-mode cyclization of allenes.
abstract: A new procedure for constructing monocyclic five- and six-membered azacycles by the endo-mode ring-closing reaction of allenylazido derivatives under neutral conditions has been developed. The azabicyclo[m.n.0] compounds were prepared by applying this newly developed procedure. The seven-membered azacycle was prepared when the allene possessing an unsubstituted carboxyl amido functionality was submitted to the basic conditions. In addition, indole and quinoline skeletons were synthesized using this procedure.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi 13-1, Kanazawa 920-0934, Japan. cmukai@kenroku.kanazawa-u.ac.jp
authors.forename: Chisato
authors.initials: C
authors.lastname: Mukai
authors.forename: Minoru
authors.initials: M
authors.lastname: Kobayashi
authors.forename: Shoko
authors.initials: S
authors.lastname: Kubota
authors.forename: Yukie
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Shinji
authors.initials: S
authors.lastname: Kitagaki
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000586:Amination; D001372:Aza Compounds / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014220:Trialkyltin Compounds
chemical_list: D000466:Alkadienes; D000480:Alkynes; D000577:Amides; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D006571:Heterocyclic Compounds; D007211:Indoles; D020005:Propanols; D011804:Quinolines; D014220:Trialkyltin Compounds; C025947:propadiene; C011559:tributyltin; C028255:propargyl alcohol