A convenient
approach to 2-(1-ethoxyalkoxy)-3-cyanoquinolines (in
up to 50% yields) has been developed. The approach comprises functionalization
of quinolines with acetals of cyanopropargylic alcohols (KOH/H2O/MeCN, 55–60 °C) followed by their transformation
to furo[3,4-b]quinolinones (in up to 98% yields)
via the sequential removal of acetal protection and intramolecular
cyclization/hydration (7% aqueous HCl, acetone, 20–25 °C).