Formation of enehydrazine intermediates through coupling of phenylhydrazines with vinyl halides: entry into the Fischer indole synthesis.

Angew Chem Int Ed Engl. 2013 Jan 21;52(4):1266-9.

Zhan F, Liang G.

State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China. 

 

Abstract

 

Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the Akuammiline alkaloid vincorine.

 

 

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