Construction of azacycles based on endo-mode cyclization of allenes.
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.
Mukai
Chisato
C
Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi 13-1, Kanazawa 920-0934, Japan. cmukai@kenroku.kanazawa-u.ac.jp
Kobayashi
Minoru
M
Kubota
Shoko
S
Takahashi
Yukie
Y
Kitagaki
Shinji
S
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
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