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Acid-Promoted Cyclization of α‑Azidobenzyl Ketones through CN Bond Formation: Synthesis of 6‑Substituted Quinoline Derivatives
An acid-promoted cyclization of α-azidobenzyl ketones
has
been developed for the synthesis of 6-substituted quinoline derivatives.
A variety of synthetically useful 6-OTf or -OMs quinoline derivatives
were obtained in moderate to good yields. The reaction proceeds via
CN bond formation without organophosphine, providing convenient
access to structurally interesting and synthetically important 6-substituted
quinoline derivatives in moderate to good yields. A mechanistic perspective
that is different from the traditional intramolecular Schmidt reaction
has been proposed