Correction to Synthesis of N -Alkenyl 2-Pyridonyl Ethers via a Au(I)-Catalyzed Rearrangement of 2-Propargyloxypyridines
Correction to Synthesis of N -Alkenyl 2-Pyridonyl Ethers via a Au(I)-Catalyzed Rearrangement of 2-Propargyloxypyridines
复制标题
通过 Au(I) 催化 2-炔丙氧基吡啶重排校正 N-烯基 2-吡啶酮醚的合成
DOI：
10.1021/acs.joc.0c00151
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Anderson, Carolyn E.
中科院分区：
文献类型：
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作者：
Romero, Evan O.;Reidy, Connor P.;Bootsma, Andrea N.;PreFontaine, Noah M.;Vryhof, Nicholas W.;Wierenga, David C.;Anderson, Carolyn E.
n -烷基2-吡啶酮和其他烯化杂环化合物是重要的合成结构，因为它们普遍存在于天然产物和药物靶标中，并且能够作为许多生物和化学过程的模型。本发明的Au (I)催化反应利用2-丙炔氧基吡啶获得n -烷基化的2-吡啶酮产物，该产物是由环氮加成到悬垂的炔上得到的。经过广泛的优化，发现联芳基Au (I)催化剂21为1,1 -二取代醚产物8提供了最高的选择性和产率组合。在此，我们报道了这种新的Au (I)催化的C−N键形成在制备各种2-吡啶基醚类似物中的应用，这些类似物有可能作为合成含N-烷基2-吡啶酮络合物框架的切入点。结论：经过广泛的优化，发现联芳基催化剂21有利于1,1 -二取代醚8和26的选择性生成。虽然n -烷基- 2-吡啶醚8和26的分离产率仍然不大（12个例子，产率为22 - 58%），但这类化合物作为将n -烷基- 2-吡啶酮安装到一系列复杂支架中的切入点是重要的，使得该方法朝着将该基序包含到感兴趣的目标中迈出了重要的一步。
N-Alkyl 2-pyridones and other enolizable heterocycles are important synthetic constructs, due to their prevalence in natural products and pharmaceutical targets and their capacity to serve as models for a number of biological and chemical processes. The disclosed Au (I)-catalyzed reaction utilizes 2-propargyloxypyridines to access N-alkylated 2-pyridone products derived from addition of the ring nitrogen to the pendent alkyne. After extensive optimization, biaryl Au (I) catalyst 21 was found to provide the highest combination of selectively and yield for the 1, 1-disubstituted ether product 8. Herein, we report the application of this new Au (I)-catalyzed C− N bond formation for the preparation of a variety of 2-pyridonyl ether analogues, which have the potential to serve as an entry point for the synthesis of complex N-alkyl 2-pyridone-containing frameworks. Conclusion: After extensive optimization, biaryl catalyst 21 has been found to facilitate the selective formation of 1, 1-disubstituted ethers8and26. While the isolated yields ofN-alkyl 2-pyridonyl ethers 8 and 26 remain modest (12 examples, 22− 58% yield), the usefulness of this class of compounds as an entry point for the installation of N-alkyl 2-pyridones into a range of complex scaffolds is significant, rendering this method an important step toward the inclusion of this motif into targets of interest.