Mao Haibin, Lin Aijun, Tang Zhongkai, Hu Hongwen, Zhu Chengjian, Cheng Yixiang
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093 (P. R. China).
Chemistry. 2014 Feb 24;20(9):2454-8. doi: 10.1002/chem.201304295. Epub 2014 Feb 2.
A biologically inspired organocatalytic one-pot synthesis of highly functionalized pyridazines, which are ubiquitous structural units in a number of biologically active compounds, has been developed by starting from readily available diazo compounds and Morita-Baylis-Hillman (MBH) carbonates. Under mild reaction conditions, this synthetic route tolerated significant substrate variation to deliver a broad range of substituted products, including CF3 -substituted pyridazines derivatives. Moreover, the introduction of trifluoromethyl groups into the ring of pyridazine could be completed conveniently from 2,2,2-trifluorodiazoethane.
从易得的重氮化合物和森田-贝利斯-希尔曼(MBH)碳酸酯出发,开发了一种受生物启发的有机催化一锅法合成高度官能化哒嗪的方法,哒嗪是许多生物活性化合物中普遍存在的结构单元。在温和的反应条件下,该合成路线能够耐受显著的底物变化,以提供广泛的取代产物,包括CF3取代的哒嗪衍生物。此外,将三氟甲基引入哒嗪环可方便地由2,2,2-三氟重氮乙烷完成。