Synthesis of substituted indoles from 2-azidoacrylates and ortho-silyl aryltriflates.
2-Azidoacrylates react with benzynes in the presence of PPh(3) and CsF to afford substituted indoles in good yields. The reaction involves the formation of iminophosphorane and benzyne and a subsequent double cyclization/hydrolysis/air-oxidation cascade. This methodology was utilized to synthesize 10H-indolo[1,2-a]indol-10-ones.
Hong
Deng
D
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China.
Chen
Zhengbo
Z
Lin
Xufeng
X
Wang
Yanguang
Y
D000179:Acrylates / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*
D000179:Acrylates; D001386:Azides; D007211:Indoles; D017646:Organosilicon Compounds; C036658:acrylic acid