通过将锂化炔酰胺加成到芳基亚胺上简便合成γ-氨基炔酰胺。观察到迈耶-舒斯特重排反应。
A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an -Meyer-Schuster Rearrangement.
作者信息
Qi Rui, Wang Xiao-Na, Dekorver Kyle A, Tang Yu, Wang Chao-Chao, Li Qian, Li Hui, Lv Ming-Can, Yu Qing, Hsung Richard P
机构信息
School of Pharmaceutical Science and Technology, and Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin 300072 P. R. China.
出版信息
Synthesis (Stuttg). 2013 Jul 1;45(13):1749-1758. doi: 10.1055/s-0033-1338476.
Abstract
Efforts in developing an expeditious and convenient method for synthesizing γ-amino-ynamides via nucleophilic addition of lithiated ynamides to aryl imines are described. This work also features an -variant of a Meyer-Schuster rearrangement of γ-amino-ynamides and the synthetic utility of γ-amino-ynamides in an intramolecular ketenimine-[2 + 2] cycloaddition.
摘要
本文描述了通过将锂化炔酰胺对芳基亚胺进行亲核加成来开发一种快速便捷的合成γ-氨基炔酰胺方法的研究工作。这项工作还包括γ-氨基炔酰胺的迈耶-舒斯特重排变体以及γ-氨基炔酰胺在分子内烯酮亚胺-[2 + 2]环加成反应中的合成应用。
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本文引用的文献
1
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2
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Org Lett. 2013 Apr 5;15(7):1752-5. doi: 10.1021/ol400560m. Epub 2013 Mar 25.
3
Ag- and Au-catalyzed addition of alcohols to ynimides: β-regioselective carbonylation and production of oxazoles.Ag 和 Au 催化醇对炔酰胺的加成：β-区域选择性羰基化和唑的生成。
Org Lett. 2013 Apr 5;15(7):1560-3. doi: 10.1021/ol400338x. Epub 2013 Mar 15.
4
Synthesis of functionalized allenamides from ynamides by enolate Claisen rearrangement.通过烯醇负离子 Claisen 重排由炔酰胺合成官能化的烯丙酰胺。
Org Lett. 2013 Apr 5;15(7):1626-9. doi: 10.1021/ol400402n. Epub 2013 Mar 15.
5
Alkane C-H insertion by aryne intermediates with a silver catalyst.芳炔中间体与银催化剂作用下的烷烃 C-H 插入反应。
J Am Chem Soc. 2013 Mar 27;135(12):4668-71. doi: 10.1021/ja400477r. Epub 2013 Mar 14.
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Angew Chem Int Ed Engl. 2013 Mar 18;52(12):3478-80. doi: 10.1002/anie.201209975. Epub 2013 Feb 12.
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