Synthesis of substituted indoline and carbazole by benzyne-mediated cyclization-functionalization.

Toshiharu Noji, Hideto Fujiwara, Kentaro Okano, Hidetoshi Tokuyama

Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan.

Organic letters 2013 Apr 19

filter terms:

A benzyne-mediated synthesis of substituted indolines and carbazoles was developed. The reaction includes generation of benzyne using Mg(TMP)2·2LiCl as a base, cyclization, and trapping the resulting organomagnesium intermediate with an electrophile to provide a series of substituted indolines and carbazoles in a regiospecific manner. This was applied to a concise five-pot total synthesis of heptaphylline.

Citation

Toshiharu Noji, Hideto Fujiwara, Kentaro Okano, Hidetoshi Tokuyama. Synthesis of substituted indoline and carbazole by benzyne-mediated cyclization-functionalization. Organic letters. 2013 Apr 19;15(8):1946-9