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Synthesis of novel 5,7-disubstituted 8-hydroxyquinolines

✍ Scribed by Banacer Himmi; Saïd Kitane; Abdelhamid Eddaif; Jean-Pierre Joly; Fouzia Hlimi; Mohamed Soufiaoui; Abdelmejid Bahloul; Abdelfatah Sebban

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
287 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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 ^1^H and ^13^C‐NMR, MS and IR spectrometric data. The X‐ray structure of the product obtained from 5‐cyanomethyl‐8‐hydroxyquinoline and piperidine is also reported.

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