An Efficient Amide-Aldehyde-Alkene Condensation: Synthesis for the N-Allyl Amides
An Efficient Amide-Aldehyde-Alkene Condensation: Synthesis for the N-Allyl Amides
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高效的酰胺-醛-烯烃缩合：N-烯丙基酰胺的合成
DOI：
10.1002/tcr.201500212
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发表时间：
2016
期刊：
影响因子：
6.6
通讯作者：
Wang Xi-Cun
中科院分区：
文献类型：
--
作者：
Quan Zheng-Jun;Wang Xi-Cun
烯丙胺骨架代表了一类重要的生物活性氮化合物，它们存在于各种天然产物和药物中，具有公认的药理学特性。在这篇个人文章中，我们将简要讨论烯丙胺骨架的合成。我们将重点展示通过酰胺-醛-烯烃缩合反应对缺电子 N-杂环酰胺和磺酰胺进行路易斯酸催化 N-烯丙基化的通用方案。将讨论 N-杂环酰胺、醛和烯烃的底物范围。该方法还能够以N-甲基-1-萘酰胺或(萘-1-基甲基)氨基甲酸甲酯与多聚甲醛和苯乙烯一锅法制备萘替芬基序。
The allylamine skeleton represents a significant class of biologically active nitrogen compounds that are found in various natural products and drugs with well‐recognized pharmacological properties. In this personal account, we will briefly discuss the synthesis of allylamine skeletons. We will focus on showing a general protocol for Lewis acid‐catalyzed N‐allylation of electron‐poor N‐heterocyclic amides and sulfonamide via an amide‐aldehyde‐alkene condensation reaction. The substrate scope with respect to N‐heterocyclic amides, aldehydes, and alkenes will be discussed. This method is also capable of preparing the Naftifine motif from N‐methyl‐1‐naphthamide or methyl (naphthalene‐1‐ylmethyl)carbamate, with paraformaldehyde and styrene in a one‐pot manner.