SYNTHESIS OF 1,2,3,4-TETRAHYDROQUINOLINES AND 1,2,3,4-TETRAHYDRO-1,6-NAPHTHYRIDINES BY A DIRECTED LITHIATION REACTION

Article abstract of DOI:10.1016/S0040-4039(00)82173-5

N-(tert-butoxycarbonyl)anilines (7), are easily converted in a one pot reaction sequence into the N-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinolines (8), by directed ortho lithiation followed by reaction with 1-chloro-3-iodopropane, hence providing a new versatile quinoline ring nucleus synthesis.In an analogous reaction 2-N-(tert-butoxycarbonyl)- and an 2-N-(pivaloylamino)pyridine are converted to 1,2,3,4-tetrahydro-1,6-naphthyridines.