Generation of N-(tert-butoxycarbonyl)indole-2,3-quinodimethane and its [4+2]-type cycloaddition.
The two conditions for the preparation of the reactive N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane intermediate were developed by the reaction of the N-(tert-butoxycarbonyl)-2-(1-ethoxycarbonyloxymethylallenyl)aniline with K(2)CO(3) or Pd(2)(dba)(3) in refluxing toluene. The resulting N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane was captured by several alkenyl and alkynyl dienophiles to provide the corresponding tetrahydro- and dihydrocarbazole derivatives.
Inagaki
Fuyuhiko
F
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Mizutani
Masaya
M
Kuroda
Norikazu
N
Mukai
Chisato
C
D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D011188:Potassium / Q000737:chemistry
D000475:Alkenes; D000480:Alkynes; D000814:Aniline Compounds; D002254:Carbonates; D007211:Indoles; C552379:N-(tert-butoxycarbonyl)indole-2,3-quinodimethane; D009942:Organometallic Compounds; C532099:tris(dibenzylideneacetone)dipalladium; C037593:potassium carbonate; D011188:Potassium; C023650:aniline