Trifluoromethyl-containing N-acylmethylenequinone imines as novel highly electrophilic agents

The strategy of searching for highly electrophilic agents in a class of chemically inert compounds – methylenequinone imines – was developed and successfully performed. The first representative of such electrophiles – N-acyl-α-methoxycarbonyl-α-trifluoromethyl-p-methylenequinone imine 6 – was synthesized. Its reactions with N-, O- and C-nucleophiles were investigated that gave various derivatives of α-trifluoromethyl-α-amino(oxy) acids as well as ß,ß,ß-trifluoropropionic acids. 3-Chloro-3-trifluoro-1,3-dihydroindol-2-ones were first obtained and their reactions with nucleophiles were studied with 1-aza-3-trifluoroindene-2-ones being formed as intermediates.

Graphical abstractThe first highly electrophilic CF3-containing agents of the N-acylmethylenequinone imine class have been prepared. Their reactions with N-, O-, and C-nucleohiles have been studied.Figure optionsDownload full-size imageDownload as PowerPoint slide