The synthesis of the hitherto unreported 1-alkyl-1,4-dihydro-4-(ethylimino or arylimino)-3-quinoline-carboxylates is described. The method utilises a 2-halogeno-benzenecarboximidoyl chloride for C-imidoylation of an ethyl 3-alkylamino-2-butenoate or 2-propenoate. With the use of ethyl 3-amino-2-butenoate as enamine the ultimate reaction product is a 2-methyl-4-arylamino-3-quinolinecarboxylate. The 2-CH3 protons of the 4-iminoquinoline esters undergo exchange in D2O/CDCl3 at room temperature.
|Number of pages
|South African Journal of Chemistry
|Published - Jun 1998