Three-component synthesis of substituted β-(trifluoromethyl)pyrroles via Grob cyclization of 1,1,1-trifluoro-3-nitrobut-2-ene with 1,3-dicarbonylic compounds and ammonia or primary amines

A variety of substituted β-(trifluoromethyl)pyrroles were easily synthesized in good yields by a one-pot, three-component Grob cyclization of 1,1,1-trifluoro-3-nitrobut-2-ene with 1,3-dicarbonyls (ethyl acetoacetate, acetylacetone, benzoylacetone) and ammonia or primary aliphatic amines.

A variety of substituted β-(trifluoromethyl)pyrroles were easily synthesized in good yields by a one-pot, three-component Grob cyclization of 1,1,1-trifluoro-3-nitrobut-2-ene with 1,3-dicarbonylic compounds (ethyl acetoacetate, acetylacetone, and benzoylacetone) and ammonia or primary aliphatic amines.Figure optionsDownload as PowerPoint slideHighlights
► 1,1,1-Trifluoro-3-nitrobut-2-ene, 1,3-dicarbonylic compounds, and ammonia or primary amines were used.
► Three-component synthesis of highly substituted β-(trifluoromethyl)pyrroles was described.
► The reaction slightly depends on the substituent of the active methylene compound.