461383-68-6Relevant academic research and scientific papers
Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
, p. 2298 - 2302 (2021/04/05)
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
Potassium Hydroxide-Catalyzed Chemoselective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of ω-Hydroxylactams and Lactams
Ding, Guangni,Li, Chengjun,Shen, Yifan,Lu, Bin,Zhang, Zhaoguo,Xie, Xiaomin
, p. 1241 - 1250 (2016/04/26)
Potassium hydroxide-catalyzed hydrosilylation exhibits excellent activity and chemoselectivity for the reduction of cyclic imides under mild reaction conditions. The chemoselectivity of the reduction system may be readily tuned by changing the identity an
Toward improving the chemistry of N-acyliminium ions: Nucleophilic substitution reactions of pyrrolidinone derivatives with trialkylsilyl nucleophiles catalyzed by triisopropylsilyltrifluoromethane sulfonate (TIPSOTf)
Othman, Raja Ben,Bousquet, Till,Fousse, Anthony,Othman, Mohamed,Dalla, Vincent
, p. 2825 - 2828 (2007/10/03)
(Chemical Equation Presented) Nucleophilic substitution reactions of racemic and chiral 5-acetoxy-, 5-ethoxy-, and 5-methoxypyrrolidin-2-ones by silicon-based nucleophiles were efficiently catalyzed by TIPSOTf. This process was found to be general and acc
Isoindolinones via a room temperature palladium nanoparticle-catalysed 3-component cyclative carbonylation-amination cascade
Grigg, Ronald,Zhang, Lixin,Collard, Simon,Keep, Ann
, p. 6979 - 6982 (2007/10/03)
A room temperature 3-component cascade process involving nucleophilic substitution/carbonylation/amination, catalysed by palladium nanoparticles generated in situ from palladacycle 5, affords isoindolinones in good yields. The conversions correlate with the pKa values of the amines.
Intramolecular Cyclization of Acyl Radicals onto the Azido Group: A New Radical Approach to Cyclized Lactams
Benati, Luisa,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Spagnolo, Piero,Strazzari, Samantha,Zanardi, Giuseppe
, p. 3079 - 3081 (2007/10/03)
(Equation Presented) Reagents: i, Bu3SnH/AlBN; ii, (TMS)3SiH/AlBN. Aryl- and alkyl-derived azidoacyl radicals, generated from thiolesters by intramolecular homolytic substitution at the sulfur, can undergo five- and six-membered cyclization onto the azido moiety to give cyclized lactams.
