Bai Hairui, Liu Fujun, Wang Xiaojing, Wang Ping, Huang Chao
School of Chemistry and Environment and Engineering Research Center of Biopolymer Functional Materials of Yunnan, Yunnan Minzu University, Yuehua Street, Kunming 650500, P. R. China.
ACS Omega. 2018 Sep 14;3(9):11233-11251. doi: 10.1021/acsomega.8b01378. eCollection 2018 Sep 30.
The development of a clear chemical process to produce diverse value-added chemicals from low-cost raw materials is a particularly attractive concept and represents a considerable challenge in sustainable organic synthesis. Herein, two highly efficient and clear methods for the synthesis of quinolone derivatives based on a linear/branched domino protocol under sustainable conditions were established. The main advantages of these protocols are the simple experimental procedure, high bond-forming efficiency, inexpensive readily available starting materials, moderate to excellent yields with good functional group compatibility, and nonchromatographic purification, which render these methods particularly attractive for the sustainable preparation of biologically and medicinally interesting molecules. To demonstrate the practical utility of our protocol, existing pharmaceutical sarafloxacin was successfully synthesized. Furthermore, a postulated reaction pathway including condensation reaction/nucleophilic aromatic substitution/Friedel-Crafts reaction for these domino reactions is also discussed.
开发一种从低成本原料生产多种增值化学品的清晰化学工艺是一个特别有吸引力的概念，也是可持续有机合成中一项相当大的挑战。在此，建立了两种基于线性/支化多米诺反应模式在可持续条件下合成喹诺酮衍生物的高效且清晰的方法。这些反应模式的主要优点是实验步骤简单、成键效率高、起始原料廉价易得、产率适中至优异且官能团兼容性良好，以及无需柱色谱纯化，这使得这些方法对于可持续制备具有生物学和医学意义的分子特别有吸引力。为了证明我们反应模式的实际效用，成功合成了现有的药物沙拉沙星。此外，还讨论了这些多米诺反应的一个假定反应途径，包括缩合反应/亲核芳香取代/傅克反应。
