1418129-48-2Relevant 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.
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.).
Synthetic approach for constructing the 1-oxygenated carbazole core and its application to the preparation of natural alkaloids
Bautista, Rafael,Jerezano, Alberto V.,Tamariz, Joaquin
, p. 3327 - 3336,10 (2012/12/11)
An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.
Synthetic approach for constructing the 1-oxygenated carbazole core and its application to the preparation of natural alkaloids
Bautista, Rafael,Jerezano, Alberto V.,Tamariz, Joaquín
, p. 3327 - 3336 (2013/01/15)
An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine. Georg Thieme Verlag Stuttgart · New York.
