Three-component synthesis of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chromene derivatives

A variety of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chromene derivatives were achieved via a one-pot, three-component reaction from easily available methyl 2-perfluoroalkynoate, malononitrile (or ethyl cyanoacetate), and diverse cyclic 1,3-diketones. Moderate to good yields (up to 93%) were obtained in the presence of catalytic methylamine. This process went through a tandem Michael addition–cyclization reaction and was mild and easily performed.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide