二氧六环水介质中 5(6,7,8)-硝基喹啉 N-氧化物的氧化 SNH 烷基化反应

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-11-06 DOI:10.1002/ejoc.202401060
Alexander Nikolaevich Larin, Elena Kimovna Avakyan, Oleg Demidov, Anastasia Alekseevna Borovleva, Alexander A. Zubenko, Diana Yu. Pobedinskaya, Artem Pavlovich Ermolenko, Stepan E. Kolosov, Ivan V. Borovlev
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引用次数: 0

摘要

本文介绍了一种新颖高效的方法,用于合成 5、6、7 和 8-硝基喹啉 N-氧化物的 2-烷基氨基和 2-二烷基氨基衍生物,这些衍生物含有药效喹啉片段,可能具有生物活性。在铁氰化钾存在下,5(6,7,8)-硝基喹啉 N-氧化物与各种伯胺或仲胺在二噁烷水溶液介质中发生反应,得到相应的仲胺和叔胺,收率中等到极好。该反应是第一个在温和条件下通过 Chichibabin 反应在第 2 位形成 2-烷基氨基喹啉衍生物的实例。对一些产物的抗菌活性进行了研究。
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An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium
A novel and efficient method for the synthesis of 2-alkylamino and 2-dialkylamino derivatives of N-oxides of 5-, 6-, 7- and 8-nitroquinolines, which can potentially exhibit biological activity, as containing a pharmacophoric quinoline fragment, is described herein. The reactions of 5(6,7,8)-nitroquinoline N-oxides with various primary or secondary amines in the presence of potassium ferricyanide at in aqueous dioxane medium afforded the corresponding secondary and tertiary amines in moderate to excellent yields. This reaction is the first example of a Chichibabin reaction leading to the formation of 2-alkylaminoquinoline derivatives at position 2 under mild conditions. A study of the antibacterial activity of some products was carried out.
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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