A novel generation of indole-2,3-quinodimethanes.
[reaction: see text] A novel and efficient procedure for the generation of the reactive indole-2,3-quinodimethane intermediates from the allenylanilines is described. The indole-2,3-quinodimethane intermediates were captured by several dienophiles to afford the corresponding tetrahydro- and dihydrocarbazole derivatives. This method is significantly different from the previously reported ones, which involve the 1,4-elimination or its related reactions of the indole derivatives that possess suitable substituents at both the C-2 and C-3 positions.
Kuroda
Norikazu
N
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Takahashi
Yukie
Y
Yoshinaga
Kazuo
K
Mukai
Chisato
C
D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000814:Aniline Compounds; D007211:Indoles; D008697:Methane