Preparation of 3-haloquinolines from 3-amino-2-halo-2-alkenimines
Preparation of 3-haloquinolines from 3-amino-2-halo-2-alkenimines
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DOI：
10.1021/jo9600215
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发表时间：
1996-10-04
影响因子：
3.6
通讯作者：
Anon, E
中科院分区：
文献类型：
--
作者：
Campos, PJ;Tan, CQ;Anon, E
喹啉环系统存在于天然产物中，尤其是生物碱。喹啉骨架通常用于设计许多具有药理学特性的合成化合物，例如硝羟喹啉、氯喹（抗疟疾化合物的一个例子）、四氢喹啉衍生物奥曲喹（用于根除血吸虫，这是热带地区疾病的主要原因）和喹诺酮衍生物（显示出高抗菌活性）。2特别是，含卤素的喹啉是显着的兴趣，因为卤素原子有时在生物活性化合物中发挥关键作用，它们提供了进一步的结构阐述的途径。3我们以前曾报道过通过辐射3-氨基-2-烯亚胺合成取代的喹啉（方案1）。4考虑到卤代喹啉底物的重要性，我们对卤代烯亚胺的光化学行为进行了研究。考虑到我们在与双（吡啶）碘鎓（I）四氟硼酸盐5的碘化反应中的经验和3-氨基-2-烯亚胺在2-位的官能化的简单性，6，7，我们进行了3-氨基-2-碘-2-烯亚胺的制备（方案2）。[8]我们在此报告了3-氨基-2-卤代-2-烯亚胺的辐照结果。
The quinoline ring system occurs in natural products, especially alkaloids. 1 The quinoline skeleton is often used for the design of many synthetic compounds with pharmacological properties such as nitroxaline, chloroquine, which is one example of an antimalarial compound, the tetrahydroquinoline derivative oxamniquine, which is used to eradicate blood flukes, a major cause of disease in tropical regions, and quinolone derivatives, which show a high antibacterial activity. 2 In particular, halogencontaining quinolines are of significant interest because halogen atoms sometimes play a pivotal role in bioactive compounds and they provide a further avenue for structural elaboration. 3We have previously reported the synthesis of substituted quinolines by irradiation of 3-amino-2-alkenimines (Scheme 1). 4 Considering the significance of the haloquinoline substrates, we undertook a study of the photochemical behavior of halo-functionalized alkenimines. Taking into account our experience in iodination reactions with bis (pyridine) iodonium (I) tetrafluoroborate5 and the simplicity of functionalization of 3-amino-2-alkenimines at the 2-position, 6, 7 we carried out the preparation of 3-amino-2-iodo-2-alkenimines (Scheme 2). 8 We report here the results obtained for the irradiation of 3-amino-2-halo-2-alkenimines.