Divergent pathways for reactions of CF3-containing Isobenzofuran-1-ones and amines.

Graphical abstract R N H 2 : 12 examples including bifunctional reagents. *R 2 N H: only cyclic sec -amines, and no reactions for the corresponding acyclic counterpart. Highlights • Facile construction of CF 3 -containing γ-lactams starting from primary amines. • Further cyclization from the product using 2-aminoethanol. • Net substitution reactions from cyclic secondary amines. Abstract Unprecedented isobenzofuran-1-ones (phthalides) with CF 3 and ethoxy groups both at the 3-position were readily synthesized from the corresponding aromatic 1,2-diesters and reacted with a variety of primary amines to find out convenient conversion to the corresponding γ-lactams, while secondary amines behaved in a totally different manner to affect the net substitution reactions for the EtO moiety, where characteristics of the strongly electron-withdrawing CF 3 group was considered to play a significantly important role. [ABSTRACT FROM AUTHOR]