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-1-甲基-2,3,3,4,5,9-六氢-1-吡咯并-[3,2]异喹啉/[2,3-]喹啉甲亚胺叶立德-烯烃[3+2]环加成反应的快速合成

Expeditious synthesis of -1-methyl-2, 3,3,4,5,9-hexahydro-1-pyrrolo-[3,2]isoquinoline / [2,3-]quinoline azomethine ylide-alkene [3+2] cycloaddition.

作者信息

Zhang Zhenfa, Dwoskin Linda P, Crooks Peter A

机构信息

College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.

出版信息

Tetrahedron Lett. 2011 May 25;52(21):2667-2669. doi: 10.1016/j.tetlet.2011.03.065.

DOI:10.1016/j.tetlet.2011.03.065
PMID:23908558
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3727292/
Abstract

Expeditious syntheses of -1-methyl-2,3,3,4,5,9-hexahydro-1-pyrrolo-[3,2]isoquinoline /[2,3-]quinoline have been developed. The syntheses started with commercially available material and afforded excellent overall yields in straightforward steps. Intramolecular azomethine ylide-alkene [3+2] cycloaddition is the key step in the construction of these pyrroloisoquinoline and pyrroloquinoline scaffolds. This route is much more atom-economic than those reported in the literature and appropriate for scale-up synthesis.

摘要

已开发出-1-甲基-2,3,3,4,5,9-六氢-1-吡咯并-[3,2]异喹啉/[2,3-]喹啉的快速合成方法。该合成以市售原料开始，通过简单步骤获得了优异的总收率。分子内甲亚胺叶立德-烯烃[3+2]环加成是构建这些吡咯并异喹啉和吡咯并喹啉骨架的关键步骤。该路线比文献报道的那些路线具有更高的原子经济性，适合放大合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/33a70b63cdbf/nihms286975f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/df7af86c52bc/nihms286975f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/c905be126afe/nihms286975f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/8b950e4d9634/nihms286975f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/a59cc36766d2/nihms286975f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/33a70b63cdbf/nihms286975f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/df7af86c52bc/nihms286975f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/c905be126afe/nihms286975f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/8b950e4d9634/nihms286975f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/a59cc36766d2/nihms286975f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/63f9/3727292/33a70b63cdbf/nihms286975f5.jpg

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