Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Chemistry Department, Faculty of Science, King Abdulaziz University (KAU) , 21589 Jeddah, Saudi Arabia.
Org Lett. 2017 Mar 3;19(5):1020-1023. doi: 10.1021/acs.orglett.7b00001. Epub 2017 Feb 20.
A novel and atom-economical synthesis of fully substituted 4-aminoimidazoles via gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides is reported. This protocol represents a new strategy to access α-imino gold carbenes, which corresponds to an unprecedented intermolecular transfer of N-acylimino nitrenes to ynamides. Moreover, the reaction proceeds with 100% atom economy, exhibits good functional group tolerance, and can be conducted in gram scale.
本文报道了一种通过金催化 1,2,4-噁二唑与炔酰胺的选择性[3+2]环化反应,全新且原子经济性的合成全取代 4-氨基咪唑的方法。该方案代表了一种获得α-亚氨基金卡宾的新策略,这对应于 N-酰亚氨基氮烯向炔酰胺的前所未有的分子间转移。此外,该反应具有 100%的原子经济性,表现出良好的官能团耐受性,并且可以进行克级规模的反应。