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Synthesis of novel 5,7‐disubstituted 8‐hydroxyquinolines
Author(s) -
Himmi Banacer,
Kitane Saïd,
Eddaif Abdelhamid,
Joly JeanPierre,
Hlimi Fouzia,
Soufiaoui Mohamed,
Bahloul Abdelmejid,
Sebban Abdelfatah
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450411
Subject(s) - chemistry , piperidine , morpholine , pyrrolidine , yield (engineering) , azide , nucleophile , amine gas treating , mannich reaction , 8 hydroxyquinoline , mannich base , cyanide , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
AbstractSeven 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.