A simple heterocyclic fusion reaction and its application for expeditious syntheses of rutaecarpine and its analogs
A simple heterocyclic fusion reaction and its application for expeditious syntheses of rutaecarpine and its analogs
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DOI：
10.1016/j.tetlet.2014.04.120
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发表时间：
2014-06-25
影响因子：
1.8
通讯作者：
Decker, Michael
中科院分区：
文献类型：
--
作者：
Huang, Guozheng;Roos, Dominika;Decker, Michael
在寻找新的胆碱酯酶抑制剂的过程中，发现了靛红酸酐8和3，4-二氢异喹啉22的简单杂环融合反应，该反应涉及加热时的自发脱氢。应用该反应，可以分别合成生物活性天然生物碱吴茱萸次碱和色胺与邻氨基苯甲酸或靛红酸酐的几种取代衍生物，而无需繁琐的色谱纯化。这为在药物化学中获得大量具有这种特殊结构的化合物提供了简单和快速的途径。(C)2014爱思唯尔有限公司版权所有。
In the search for new inhibitors of cholinesterases, a simple heterocyclic fusion reaction of isatoic anhydride 8 and 3,4-dihydroisoquinoline 22 was discovered which involves a spontaneous dehydrogenation upon heating. Applying the reaction, the bioactive natural alkaloid rutaecarpine and several substituted derivatives out of tryptamines and anthranilic acids or isatoic anhydrides, respectively, can be synthesized without tedious chromatographic purification. This provides simple and fast access to larger amounts of compounds with this privileged structure in medicinal chemistry. (C) 2014 Elsevier Ltd. All rights reserved.