Xu Cheng, Yin Guodong, Jia Feng-Cheng, Wu Yan-Dong, Wu An-Xin
College of Chemistry and Chemical Engineering, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi 435002, P. R. China.
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.
Org Lett. 2021 Apr 2;23(7):2559-2564. doi: 10.1021/acs.orglett.1c00486. Epub 2021 Mar 19.
An unprecedented I/FeCl-promoted cascade reaction of aryl methyl ketones with 8-aminoquinolines for the convenient synthesis of ()-3-(2-acyl-1-benzo[]imidazol-4-yl)acrylaldehydes was developed by merging annulation with ring deconstruction. This novel strategy unlocked the new reactivity of 8-aminoquinolines and provided an attractive platform for the ring opening of unactivated -heteroaromatic compounds. Preliminary mechanistic investigation suggested that dual C(sp)-H amination/C-N bond cleavage were key reaction steps. Furthermore, late-stage modification of the obtained products successfully delivered pyrazole and isoxazole derivatives, increasing the practicability and application potential of this methodology in organic synthesis.
通过环化与环解构相结合，开发了一种前所未有的I/FeCl促进的芳基甲基酮与8-氨基喹啉的串联反应，用于方便地合成()-3-(2-酰基-1-苯并[]咪唑-4-基)丙烯醛。这种新颖的策略开启了8-氨基喹啉的新反应性，并为未活化的-杂芳族化合物的开环提供了一个有吸引力的平台。初步机理研究表明，双重C(sp)-H胺化/C-N键断裂是关键反应步骤。此外，对所得产物的后期修饰成功地得到了吡唑和异恶唑衍生物，增加了该方法在有机合成中的实用性和应用潜力。
