Lactam acetals : Part XXIV reaction with activated haloalkyl compounds with and without zinc

Article abstract of DOI:10.1016/S0040-4039(00)76669-X

Reaction of 2-alkoxyimmonium methosulfates (2), and of lactam acetals (3) derived therefrom, with α-haloesters in presence of zinc (Reformatsky condition) yielded N-alkyl-2-(α-alkyl-α-alkoxycarbonyl)methylene-l-azacycloalkanes (6), while reaction of 3 with α-haloesters without zinc gave 3-alkoxycarbonylmethyl-l-azacycloalkane-2-one (5). Similar reaction of 2 and 3 with 4-bromoethylquinolin-2-one (4) in presence of zinc gave N-alkyl-2-[4-(2-oxoquinolyl)methylene]-1-azacycloalkanes (7), a key intermediate for the synthesis of antimalarial quinoline-4-methanols.