14807-16-0Relevant articles and documents
Intramolecular Vilsmeier processes: a new route to cyclopenta- and cyclohexa-fused quinolines by cyclisation of adipic and pimelic bis-amides
Meth-Cohn, Otto,Goon, Simon
, p. 85 - 90 (2007/10/03)
Symmetrical and unsymmetrical bis-amides derived from adipic and pimelic acid and secondary amines react in POCl3 solution to give the title compounds by way of a Vilsmeier reagent-α-chloro enamine interaction.Adipanilide and pimelanilide only cyclise with added PCl5.However the bis-N-substituted derivatives (N-methyl or N-phenyl) of adipanilide and pimelanilide give quinolinium salts in good yield.Unsymmetrical amides with an N-substituted anilide at one end and an aliphatic unit at the other only proceed as far as the intermediate stage, giving 1,2-disubstituted cyclo-pentanes or -hexanes.Analogous amides derived from suberic and sebacic acid do not give quinolinium salts but instead give complex mixtures.