53475-33-5Relevant academic research and scientific papers
Can Primary Arylamines Form Enamine? Evidence, α-Enaminone, and [3+3] Cycloaddition Reaction
Fernando, E. H. Nisala,Cortes Vazquez, Jose,Davis, Jacqkis,Luo, Weiwei,Nesterov, Vladimir N.,Wang, Hong
, p. 14617 - 14626 (2021/10/25)
The formation of enamine from primary arylamines was detected and confirmed by nuclear magnetic resonance spectroscopy. The presence of a radical quencher, e.g., (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl, was found to be essential for the detection of enamine formation. A direct synthesis of α-enaminones from primary arylamines and ketones was also developed. Mechanistic investigation of α-enaminone formation suggests that an amine radical cation generated through O2 singlet energy transfer was involved in initiating α-enaminone formation. The reactivity and utility of α-enaminones were explored with a [3+3] cycloaddition reaction of enones affording dihydropyridines in good yields (58-85%). α-Enaminones displayed a set of reactivities that is different from that of enamines. The knowledge gained in this work advances our basic understanding of organic chemistry, providing insights and new opportunities in enamine catalysis.
Synthesis of α-enaminones from cyclic ketones and anilines using oxoammonium salt as an oxygen transfer reagent
Xu, Biping,Shang, Yaping,Jie, Xiaoming,Zhang, Xiaofeng,Kan, Jian,Yedage, Subhash Laxman,Su, Weiping
supporting information, p. 1827 - 1831 (2020/04/07)
A convenient and straightforward transformation of cyclic ketones with anilines at room temperature has been developed using oxoammonium salt TEMPO+PF6- as an oxidant. This method enabled the synthesis of a broad range of α-enaminones. The 18O-labeling experiment demonstrated that oxoammonium salt served as the oxygen transfer reagent.
Acid/Base-Co-catalyzed Direct Oxidative α-Amination of Cyclic Ketones: Using Molecular Oxygen as the Oxidant
Li, Yi-Jin,Zhang, Lu,Yan, Na,Meng, Xiang-He,Zhao, Yu-Long
supporting information, p. 455 - 461 (2017/12/04)
A novel acid/base-co-catalyzed direct intermolecular α-amination of various cyclic ketones has been developed for the first time. The reaction employs molecular oxygen as the sole oxidant under metal-free conditions. The reaction tolerates a wide range of various anilines, especially primary diamine derivatives, and provides a simple and efficient method for the constructions of α-amino enones and benzodiazepine derivatives in a single step. (Figure presented.).
Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation
Shi, Hao,Guo, Tianjian,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 2753 - 2760 (2014/04/17)
A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2- enone with hypervalent iodine reagent PhI(OCOCF3)2 (PIFA), through a direct intramolecular oxidative C(sp2)-C(sp2) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]indol-6(5H)- one skeletons. The mechanism of the process was proposed and briefly discussed.
