Synthesis of 2-heptyl-1-hydroxy-4(1H)-quinolone -: Unexpected rearrangement of 4-(alkoxycarbonyloxy)quinoline N-oxides to 1-(alkoxycarbonyloxy)-4(1H)-quinolones

被引：24
|
作者：
Woschek, Anna
Mahout, Marek
Mereiter, Kurt
Hammerschmidt, Friedrich
机构：
[1] Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
[2] Vienna Univ Technol, Inst Chem Technol & Anal, A-1060 Vienna, Austria
来源：
SYNTHESIS-STUTTGART | 2007年 / 10期
基金：
俄罗斯科学基金会;
关键词：
acylations; heterocycles; quinolines; rearrangements; oxidations;
D O I：
10.1055/s-2007-966020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Heptyl-4(1H)-quinolone was converted in two steps into the 4-ethoxycarbonyloxy-,4-(tert-butoxycarbonyloxy)-, and 4(dimethylaminocarbonyloxy)quinoline N-oxides. While the former two rearranged to the corresponding 1-(alkoxycarbonyloxy)-4(1H)quinolones at room temperature, the latter was stable, even at 140 degrees C in refluxing xylenes. Basic hydrolysis of these compounds furnished 2-heptyl-1-hydroxy-4(1H)-quinolone.
引用
收藏
页码：1517 / 1522
页数：6
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