高度扭曲的 N-酰基咪唑的结构和反应性。
Structure and Reactivity of Highly Twisted N-Acylimidazoles.
机构信息
Department of Chemistry , Yale University , 225 Prospect Street , New Haven , Connecticut 06520-8107 , United States.
出版信息
Org Lett. 2019 Apr 5;21(7):2346-2351. doi: 10.1021/acs.orglett.9b00624. Epub 2019 Mar 12.
Abstract
A modular and efficient synthesis of highly twisted N-acylimidazoles is reported. These twist amides were characterized via X-ray crystallography, NMR spectroscopy, IR spectroscopy, and DFT calculations. Modification of the substituent proximal to the amide revealed a maximum torsional angle of 88.6° in the solid state, which may be the most twisted amide reported for a nonbicyclic system to date. Reactivity and stability studies indicate that these twisted N-acylimidazoles may be valuable, namely as acyl transfer reagents.
摘要
本文报道了一种高度扭曲的 N-酰基咪唑的模块化和高效合成方法。这些扭曲酰胺通过 X 射线晶体学、NMR 光谱、IR 光谱和 DFT 计算进行了表征。对酰胺附近的取代基进行修饰，在固态中得到了最大扭转角为 88.6°，这可能是迄今为止报道的非环体系中最扭曲的酰胺。反应性和稳定性研究表明，这些扭曲的 N-酰基咪唑可能具有重要价值，例如作为酰基转移试剂。
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