4593-17-3Relevant academic research and scientific papers
Cu(II)-Mediated keto C(sp3)-H bond α-acyloxylation of N, N-dialkylamides with aromatic carboxylic acids
Li, Wenjing,Yin, Changzhen,Yang, Xiao,Liu, Hailong,Zheng, Xueli,Yuan, Maolin,Li, Ruixiang,Fu, Haiyan,Chen, Hua
supporting information, p. 7594 - 7599 (2017/09/27)
The selective oxidative coupling of aromatic carboxylic acids with the C(sp3)-H bond adjacent to the keto group of alkylamides has been developed by employing a low cost copper source. This provides an efficient approach for synthesis of O-benzoylglycolamides. The protocol displayed good functional group tolerance. A broad range of benzoic acids directly coupled with alkylamides to afford a variety of O-benzoylglycolamides in moderate to good yields. In addition, a reasonable radical mechanism was proposed based on EPR experiments.
Aqueous high-temperature chemistry of carbo- and heterocycles: Part 24 [1]. First demonstration of specific C-C bond scission of the pyridine ring. Reactions of piperidine, pyridine and some of their methyl derivatives in aqueous formic acid
Katritzky, Alan R.,Parris, Roslyn L.,Ignatchenko, Elena S.,Balasubramanian, Marudai,Barcock, Richard A.,Siskin, Michael
, p. 220 - 230 (2007/10/03)
In its reactions with the title compounds, formic acid variously acts as a formylating, methylating, and reducing agent. Both pyridine and piperidine are converted in significant amounts into 1-methyl-, 1-ethyl-, 1-propyl- and 1-pentyl-piperidines. Of the N-alkyl groups, isotopic labeling shows that only N-methyl derives from the formic acid, while the N-ethyl and N-propyl arise from heterocyclic ring C-C bond scission by retro-vinylogous-bis-aza-Aldol reactions. Detailed analysis of the products for pyridine, piperidine, and their 4-methyl derivatives, reacted separately and mixed, supports mechanisms in which a piperidine adds 1,2 to a pyridinium cation, or to a di- or tetra-hydropyridine, to initiate reaction sequences leading to the product slates found.
