Synthesis of novel 5,7-disubstituted 8-hydroxyquinolines

摘要

Seven new 5,7-disubstituted oxine derivatives have been synthesized via a Mannich reaction between a sec. amine (e.g. piperidine, pyrrolidine, morpholine, or dibenzylamine,) and 5-cyano or 5-azidomethyl-8-hydroxyquinoline, which were respectively obtained by nucleophilic displacement of 5-chloromethyl-8-hydroxyquinoline by cyanide or azide anions. In all cases, a single product was isolated in medium to fair yield and characterized on the basis of H-1 and C-13-NMR, MS and IR spectrometric data. The X-ray structure of the product obtained from 5-cyanomethyl-8-hydroxyquinoline and piperidine is also reported.