5334-06-5Relevant 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
supporting information, 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.
One-pot synthesis of pyrrolidones from levulinic acid and amines/nitroarenes/nitriles over the Ir-PVP catalyst
Chaudhari, Chandan,Nagaoka, Katsutoshi,Nishida, Yoshihide,Sato, Katsutoshi,Shiraishi, Masaya
supporting information, p. 7760 - 7764 (2020/11/27)
The synthesis of pyrrolidones via reductive amination of levulinic acid with aniline was examined over polypyrrolidone-stabilized metal nanoparticle catalysts. Among them, Ir metal was the most effective and applicable for the reductive amination of levulinic acid with nitroarenes/nitriles. Importantly, this catalyst was used for the one-pot synthesis of the anti-inflammatory drug indoprofen from 2-formylbenzoic acid and 2-(4-nitrophenyl)propanoic acid.
Reaction of phthalaldehyde with aminoethanol under different conditions: Products and mechanisms of their formation
Klima, Jiri,Polasek, Miroslav,Ludvik, Jiri,Urban, Jiri
, p. 1202 - 1209 (2013/01/15)
Analysis of amino acids and very efficient disinfection procedures are based on the reaction of phthalaldehyde (OPA) with primary amines. In this contribution, aminoethanol (=kolamin) as a nitrogen-containing nucleophile was used for the investigation of its reaction mechanism with OPA performed in basic aqueous buffered media (pH 9.5), where an influence of hydration or solvation is expected, and in anhydrous acetonitrile. Depending on the detailed reaction conditions, seven products were isolated and their structures determined by NMR, mass spectrometry, and X-ray structure analysis. Reaction mechanisms are proposed, which involve hydride transfers to OPA (Cannizzaro-type reaction).
An easy approach for the synthesis of N-substituted isoindolin-1-ones
Ordonez, Mario,Tibhe, Gaurao D.,Zamudio-Medina, Angel,Viveros-Ceballos, Jose Luis
, p. 569 - 574 (2012/05/05)
A practical and efficient two-step synthesis of N-substituted isoindolin-1-ones was developed. The one-pot reaction of 2-formylbenzoic acid with amines and dimethyl phosphite proceeds in short time either with conventional heating or microwave irradiation
Complementary synthetic approaches to constitutionally diverse N-aminoalkylated isoindolinones: Application to the synthesis of falipamil and 5-HT1A receptor ligand analogues
Lorion, Magali,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
experimental part, p. 1897 - 1903 (2010/02/16)
Different synthetic approaches for the elaboration of poly and diversely substituted isoindolinones tailed with constitutionally diverse aminoalkylated chains have been developed. The key step is based upon the preliminary assembly of the isoindolinone te
Effect of linking bridge modifications on the antipsychotic profile of some phthalimide and isoindolinone derivatives
Norman, Mark H.,Minick, Douglas J.,Rigdon, Greg C.
, p. 149 - 157 (2007/10/03)
A series of phthalimide and isoindolinone derivatives bridged to 4-(1,2- benzisothiazol-3-yl)-1-piperazinyl was prepared. The compounds were evaluated in vitro at dopamine D2 and serotonin 5-HT(1a) and 5-HT2 receptors and in vivo for their ability to antagonize the apomorphine-induced climbing response in mice. The effects of bridge length and conformation on the biological activity of these potential antipsychotic agents are discussed. A four-carbon spacer provided optimal activity within the two homologous series. Conformational investigations of the lead compound, isoindolinone 2, were conducted in an attempt to account for the superior activity observed for the butyl derivatives. On the basis of NMR and molecular modeling studies, two types of folded structures were proposed and several conformationally restrained analogues were synthesized. In general, restrictions incorporated within the linking bridge were detrimental to activity.
