Abstract
The synthesis of 1,2-dihydroquinolines by the
hydrazine-catalysed ring-closing carbonyl-olefin metathesis (RCCOM) of
N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of
substitution patterns are shown, and the compatibility of these conditions with
a range of additives is demonstrated.
With an acid-labile protecting group on the nitrogen atom, in situ
deprotection and autoxidation furnishes quinolines. In comparison to related oxygen-containing
substrates, the cycloaddition step of the catalytic cycle is shown to be
slower, but the cycloreversion is found to be more facile.