单-N-酰基炔丙基胍的区域选择性碱介导环化反应。
Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines.
机构信息
Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
出版信息
J Org Chem. 2017 Jul 7;82(13):6958-6967. doi: 10.1021/acs.joc.7b00639. Epub 2017 Jun 15.
Abstract
A regioselective base-mediated cyclization of mono-N-acylpropargylguanidines is reported. A related Ag(I)-catalyzed hydroamination strategy was recently employed to yield N-Cbz-protected ene-guanidines, which found utility in the synthesis of naamidine A. Herein, we report the base-catalyzed hydroamination of mono-N-acylpropargylguanidines, which proceeds with the opposite regiochemistry to deliver isomerized N-acyl-2-aminoimidazoles with broad substrate scope, circumventing the problematic regiospecific acylation of free 2-aminoimidazoles.
摘要
本文报道了单 N-酰基炔丙基胍的区域选择性碱介导环化反应。最近采用了一种相关的 Ag(I)催化的氢胺化策略来合成 N-Cbz 保护的烯基胍，该策略在 naamidine A 的合成中得到了应用。在此，我们报告了单 N-酰基炔丙基胍的碱催化氢胺化反应，其反应区域化学与之前报道的相反，以广泛的底物范围得到异构化的 N-酰基-2-氨基咪唑，避免了游离 2-氨基咪唑的问题区域特异性酰化。
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