通过芳炔环加成合成吡啶并[1,2-a]吲哚丙二酸盐和胺。
Synthesis of pyrido[1,2-a]indole malonates and amines through aryne annulation.
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
出版信息
J Org Chem. 2012 Mar 16;77(6):2743-55. doi: 10.1021/jo2025543. Epub 2012 Mar 6.
Abstract
Pyrido[1,2-a]indoles are known as medicinally and pharmaceutically important compounds, but there is a lack of efficient methods for their synthesis. We report a convenient and efficient route to these privileged structures starting from easily accessible 2-substituted pyridines and aryne precursors. A small library of compounds has been synthesized utilizing the developed method, affording variously substituted pyrido[1,2-a]indoles in moderate to good yields.
摘要
吡啶并[1,2-a]吲哚是一类具有重要药用和药物化学价值的化合物，但目前缺乏有效的合成方法。我们报道了一种从易得的 2-取代吡啶和芳基前体出发构建这些优势结构的简便、高效方法。利用所开发的方法合成了一系列化合物库，以中等至良好的收率得到了各种取代的吡啶并[1,2-a]吲哚。
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2
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Org Lett. 2011 Aug 5;13(15):4136-9. doi: 10.1021/ol2016803. Epub 2011 Jul 11.
3
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Org Lett. 2011 Jul 1;13(13):3340-3. doi: 10.1021/ol201086g. Epub 2011 Jun 1.
4
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J Org Chem. 2011 Jun 17;76(12):4980-6. doi: 10.1021/jo200651b. Epub 2011 May 17.
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10
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