Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes
Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes
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DOI：
10.1021/jo020020e
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发表时间：
2002-05-17
影响因子：
3.6
通讯作者：
Larock, RC
中科院分区：
文献类型：
--
作者：
Huang, QH;Hunter, JA;Larock, RC
在I-2、ICI、PhSeCl、PhSCl和P-O-2-NC6H4SCl存在下，邻(1-炔基)苯甲醛和类似的吡啶甲醛的叔丁亚胺在非常温和的反应条件下环化，分别得到相应的含卤素、硒和硫的二取代异喹啉和萘啶。该方法适用于多种亚氨基炔类化合物，并以中等至优良的产率提供预期的杂环化合物。通过金属催化的亚氨基炔类化合物的闭环反应，合成了单取代的异喹啉和萘啶类化合物。在50℃的温度下，银催化的闭环反应对芳基、烯基和烷基取代的亚氨基炔的环化反应非常有效。
The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence Of I-2, ICI, PhSeCl, PhSCl, and P-O-2-NC6H4SCl to give the corresponding halogen-, selenium-, and sulfur-containing disubstituted isoquinolines and naphthyridines, respectively. This methodology accommodates a variety of iminoalkynes and affords the anticipated heterocycles in moderate to excellent yields. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. The silver-catalyzed ring closure is highly effective in cyclizing aryl-, alkenyl-, and alkyl-substituted iminoalkynes at 50 degreesC.