[1,5]-Hydride Shift Triggered <i>N</i>-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes

Abstract

A new simple one-pot two-step protocol for the synthesis of 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate from 2-(2-(benzylamino)benzylidene)malonate under the action of BF3·Et2O was developed. It was shown that the reaction proceeds through the formation of a stable iminium intermediate containing a difluoroboryl bridge in the dicarbonyl fragment of the molecule.

Keywords

• amides
• BF₃·Et₂O
• debenzylation
• nitrogen heterocycles
• 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate