SYNTHETIC ROUTES TO QUINOLINE DERIVATIVES - NOVEL SYNTHESES OF TYRYL-8-METHOXY-4-[(2-METHYLPHENYL)AMINO]QUINOLINE AND -HYDROXYETHOXY)-4-[(2-METHYLPHENYL)AMINO]QUINOLINE

The 3,4,8-trisubstituted quinoline derivatives 2-butyryl-8-methoxy-4-[ (2-methylphenyl)amino] quinoline and yryl-8-(2-hydroxyethoxy)-4-[(2-me thylphenyl)amino] were prepared using five novel synthetic strategies, each involving a different disconnection as a basis for the key step. One such strategy led to the development of highly efficient processe s for the large-scale preparations of both compounds and featured a fa cile cyclisation of an [(arylamino)methylene]malonate and an unusual R eformatsky reaction of a quinoline-3-carboxylate with tert-butyl 2-bro mobutyrate in the presence of zinc.