A new approach to the synthesis of 2-substituted indoles: Reaction of dimetallated ortho-trimethylsilylmethylanilides with esters

Article abstract of DOI:10.1016/S0040-4020(01)86701-6

The reaction of 2-trimethylsilylmethylanilides and esters in basic medium provides a new general method for the synthesis of indoles. The advantages of this method are the mild reaction conditions (-10-0°C), the ready availability of the starting materials and the use of a non-nucleophilic base (lithium 2,2,6,6-tetramethylpiperidide) to promote cyclisation.