1188022-73-2Relevant academic research and scientific papers
Iron-Catalyzed Cyclization of Ketoxime Carboxylates and Tertiary Anilines for the Synthesis of Pyridines
Zhao, Mi-Na,Ren, Zhi-Hui,Yu, Le,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 1194 - 1197 (2016)
A novel and efficient iron-catalyzed cyclization of ketoxime carboxylates and N,N-dialkylanilines for the modular synthesis of diverse pyridines was developed. The reaction was initiated by Fe-catalyzed N-O bond cleavage of ketoxime carboxylates in the presence of tertiary anilines. The methylene carbon on N,N-dialkylanilines functioned as a source of one-carbon synthon in the reaction. The reaction used readily available starting materials, tolerated various functional groups, and afforded 2,4-disubstituted and 2,4,6-trisubstituted pyridines in good to high yields under mild conditions.
Metal-Free Assembly of Polysubstituted Pyridines from Oximes and Acroleins
Huang, Huawen,Cai, Jinhui,Tang, Lichang,Wang, Zilong,Li, Feifei,Deng, Guo-Jun
, p. 1499 - 1505 (2016/03/01)
Transition-metal-catalyzed synthesis of N-heterocycles from oximes has been previously well established. In this paper, for the first time a metal-free protocol with the combinational employment of iodine and triethylamine has been demonstrated to be effective to trigger the oxime-based synthesis of pyridines with high chemo-selectivity and wide functional group tolerance. A broad range of functional pyridines were prepared in moderate to excellent yields. While neither iodine nor triethylamine could trigger this transformation, mechanistic experiments indicated a radical pathway for the reaction. The resultant 2-aryl-substituted pyridines have been proved to be versatile building blocks in a range of transition-metal-catalyzed C-H functionalization reactions. (Chemical Equation Presented).
