29456-22-2Relevant articles and documents
Structure-activity relationships for the anaesthetic and analgaesic properties of aromatic ring-substituted ketamine esters
Bickerdike, Michael J.,Denny, William A.,Dimitrov, Ivaylo V.,Harvey, Martyn G.,Sleigh, James W.,Voss, Logan J.
, (2020/07/10)
A series of benzene ring substituted ketamine N-alkyl esters were prepared from the corresponding substituted norketamines. Few of the latter have been reported since they have not been generally accessible via known routes. We report a new general route to many of these norketamines via the Neber (oxime to α-aminoketone) rearrangement of readily available substituted 2-phenycyclohexanones. We explored the use of the substituents Cl, Me, OMe, CF3, and OCF3, with a wide range of lipophilic and electronic properties, at all available benzene ring positions. The 2- and 3-substituted compounds were generally more active than 4-substituted compounds. The most generally acceptable substituent was Cl, while the powerful electron-withdrawing substituents CF3 and OCF3 provided fewer effective analogues.
Sequential [3,3]-Sigmatropic Rearrangement/Nucleophilic Arylation of N -(Benzoyloxy)enamides towards the Preparation of Cyclic β-Aryl-β-amino Alcohols
Sato, Shohei,Takeda, Norihiko,Ueda, Masafumi,Miyata, Okiko
, p. 882 - 892 (2016/03/15)
A new method has been developed for the efficient synthesis of cyclic β-aryl-β-amino alcohol derivatives bearing a tetrasubstituted carbon center via the [3,3]-sigmatropic rearrangement of N-(benzoyl oxy)enamides followed by nucleophilic arylation reactio
A novel synthesis of carboxylic acid oxime esters catalyzed by 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate
Shi, Wei,Zhang, Jiming,Zhou, Qin,Wang, Xingjian,Qi, Xiaowei,Guo, Lianyong,Ma, Wanyong,Zhou, Jianhua
, p. 7125 - 7128 (2015/04/22)
We describe a facile synthesis of carboxylic acid oxime esters in acetonitrile from the corresponding carboxylic acids and oximes catalyzed by 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate in the presence of triethylamine at room temperature under mild conditions.
