Synthesis of novel 5,7-disubstituted 8-hydroxyquinolines
Synthesis of novel 5,7-disubstituted 8-hydroxyquinolines
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DOI：
10.1002/jhet.5570450411
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发表时间：
2008-07-01
影响因子：
2.4
通讯作者：
Sebban, Abdelfatah
中科院分区：
文献类型：
--
作者：
Himmi, Banacer;Joly, Jean-Pierre;Sebban, Abdelfatah
本文报道了7个新的5，7-二取代喹啉衍生物的合成。胺（例如哌啶、吡咯烷、吗啉或二苄胺）和5-氰基或5-叠氮甲基-8-羟基喹啉，它们分别通过氰化物或叠氮阴离子亲核置换5-氯甲基-8-羟基喹啉而获得。在所有情况下，以中等至中等产率分离单一产物，并基于（1）H和（13）C-NMR、MS和IR光谱数据进行表征。本文还报道了5-氰甲基-8-羟基喹啉与哌啶反应所得产物的X-射线结构。
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.