European Journal of Organic Chemistry p. 3816 - 3825 (2018)
Update date:2022-08-04
Topics:
Aldoshin, Alexander S.
Tabolin, Andrey A.
Ioffe, Sema L.
Nenajdenko, Valentine G.
The reaction of 2-fluoro-2-nitrostyrenes with various indoles was investigated. We found that the reaction proceeds as a Michael addition in a highly regioselective manner to form 3-(1-aryl-2-fluoro-2-nitroethyl)-1H-indoles. Thus, a green and catalyst-free synthesis of these compounds was developed using water as a reaction medium. The high effectiveness of this approach was demonstrated through the preparation of target products in up to 92 % isolated yield. Subsequent reduction of the nitro group was investigated. We found that due to the instability of the intermediate α-fluoro amines, the reduction led to non-fluorinated tryptamine derivatives.
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