1121-07-9Relevant articles and documents
Asymmetric hydrogenation of N-substituted maleimides by cultured plant cells
Hirata, Toshifumi,Takarada, Asuka,Matsushima, Akihito,Kondo, Yoko,Hamada, Hiroki
, p. 15 - 16 (2004)
The cultured suspension cells of higher plants hydrogenated the C-C double bond of N-substituted maleimides to afford the corresponding succinimides. Hydrogenation of N-phenyl-2-methylmaleimide by the cultured cells of Nicotiana tabacum proved to be highl
Zirconyl chloride: An efficient, water-tolerant, and reusable catalyst for the synthesis of N-methylamides
Talukdar, Dhrubajyoti,Saikia, Lakhinath,Thakur, Ashim Jyoti
, p. 1597 - 1601 (2011)
ZrOCl28H2O is a highly effective, water-tolerant, and reusable catalyst for the direct condensation of carboxylic acids and N,N-dimethylurea under microwave irradiation to give the corresponding N-methylamides in moderate to excellent yields. Notably, ZrOCl 28H2O is a potentially useful green catalyst due to its low toxicity, easy availability, low cost, ease of handling, easy recovery, good activity, and reusability. Georg Thieme Verlag Stuttgart ? New York.
Niobium pentachloride-mediated nucleophilic additions to cyclic N-acyliminium ions
Kleber, Carlos,Andrade,Matos, Ricardo Alexandre F.
, p. 1189 - 1191 (2003)
Niobium chloride promoted the nucleophilic addition of allyltrimethylsilane, ethyl acetoacetate, indole and the silyl enol ether derived from acetone to cyclic N-acyliminium ions. The products were obtained in good yields.
The photooxidative degradation of N-methylpyrrolidinone in the presence of Cs3PW12O40 and TiO2 colloid photocatalysts
Friesen, Duane A.,Headley, John V.,Langford, Cooper H.
, p. 3193 - 3198 (1999)
The mechanisms of the heterogeneous photocatalytic behavior of TiO2 and Cs3PW12O40 for the oxidative destruction of N-methylpyrrolidinone (NMP) in water are discussed. Both photocatalysts generate H-methylsuccinimide (NMS) and succinimide as the main intermediates from oxidation at the α-carbon and methyl positions. 2-Pyrrolidmone (2P) and 5-hydroxy-N-methylpyrrolidinone (5-HNMP) have also been identified as primary intermediates These intermediates are all broken down under further photooxidation. However, differences in product distribution indicate the possibility of several mechanistic pathways. Hydroxyl radical-like attack predominates for TiO2- photocatalyzed degradation, whereas the polyoxotungstate appears to oxidatrvely destroy NMP by both OH radical attack and direct oxidation For TiO2, the relative quantum yields for NMP oxidation (0.5 g L-1 TiO2, pH 3. 254 nm, 7 × 10-6 ein sec-1) increase from 3PW12O40 under the same conditions, the apparent quantum yield is nearly invariant (0.005-0.009) over the concentration range 10- 1000 ppm.
Rates and Mechanism in the Electron Transfer Mediated Reduction of N-Chlorosuccinimide by Succcinimide Anion.
Barry, John E.,Finkelstein, Manuel,Moore, W. Michael,Ross, Sidney D.
, p. 528 - 531 (1985)
The electrochemical reduction of N-chlorosuccinimide in acetonitrile at a platinum cathode parallels the reduction of N-bromosuccinimide.The overall n value is 1; the succinimide anion, generated by a two-electron reduction of N-chlorosuccinimide, is an intermediate; homogeneous electron transfer from the succinimide anion to N-chlorosuccinimide generates the succinimidyl radical, which is the precursor for the products formed.The reduction of N-chlorosuccinimide by the succinimide anion, added as a quaternary ammonium succinimide, in a homogeneous chemical system is significantly different from the comparable reaction with N-bromosuccinimide.Rate constants for the pertinent reactions have been measured, and reaction mechanism has been discussed.
A mild and facile synthesis of cyclic imides using pyridinium chlorochromate
Yang, Yanyan,Wang, Ge,Cao, Xiaohui,Yan, Xilong,Chen, Ligong
, p. 657 - 658,2 (2011)
A mild and facile synthetic method of cyclic imides is presented. These compounds are widely used in the synthesis of novel medical, polymeric, photonic and electronic materials. Compared with traditional syntheses, the method reported has several advantages including mild conditions, simplified work-up and low cost.
Electrochemical oxidative C(sp3)-H azolation of lactams under mild conditions
Lei, Aiwen,Wan, Zhaohua,Wang, Dan,Wang, Shengchun,Yang, Zixuan,Zhang, Heng
, p. 3742 - 3747 (2020)
Lactam-containing structural compounds are ubiquitous in drugs and biomolecules. An electrochemical oxidative direct C(sp3)-H azolation of lactams has been reported under metal catalyst-free and external chemical oxidant-free conditions. This electrochemical C(sp3)-H/N-H coupling is characterized by its broad substrate scope of azoles and lactams under mild conditions at room temperature. Mechanistic studies suggested that the reaction possibly involves a radical process. Moreover, the site selectivity can be explained by DFT calculations. More meaningfully, a gram-scale synthesis method of flow electrochemistry was employed to show the scaled-up applicability of this transformation.
Photoredox/Cobalt-Catalyzed C(sp3)-H Bond Functionalization toward Phenanthrene Skeletons with Hydrogen Evolution
Guo, Jia-Dong,Yang, Xiu-Long,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 9627 - 9632 (2020)
The first example of photoredox strategy for synthesis of phenanthrene skeletons through C(sp3)-H functionalization under external oxidant-free conditions is achieved. This transformation relies on the keto-enol tautomerism of 1,3 dicarbonyl moiety, i.e., the enol form of 1,3-dicarbonyl derivatives with relatively lower oxidation potential can be activated by the excited acridinium photocatalyst. The electron and proton eliminated from the substrate are immediately captured by a cobaloxime catalyst to exclusively afford a-carbonyl radical for highly substituted 10-phenanthrenols in good to excellent yields.
Zirconium triflate catalyzed direct coupling reaction of lactams with heterocyclic arenes under atmospheric oxygen
Tsuchimoto, Teruhisa,Ozawa, Yoshitaka,Negoro, Ryoju,Shirakawa, Eiji,Kawakami, Yusuke
, p. 4231 - 4233 (2004)
Exclusive coupling: High turnover numbers were attained in the dehydrogenative coupling reaction between C(sp2) and C(sp 3) atoms. A zirconium catalyst mediates the coupling reactions of heterocyclic arenes and lactams exclusively at the carbon atom adjacent to the nitrogen atom of the latter under an oxygen atmosphere (see scheme).
Recombinant Cyanobacteria for the Asymmetric Reduction of C=C Bonds Fueled by the Biocatalytic Oxidation of Water
K?ninger, Katharina,Gómez Baraibar, álvaro,Mügge, Carolin,Paul, Caroline E.,Hollmann, Frank,Nowaczyk, Marc M.,Kourist, Robert
, p. 5582 - 5585 (2016)
A recombinant enoate reductase was expressed in cyanobacteria and used for the light-catalyzed, enantioselective reduction of C=C bonds. The coupling of oxidoreductases to natural photosynthesis allows asymmetric syntheses fueled by the oxidation of water. Bypassing the addition of sacrificial cosubstrates as electron donors significantly improves the atom efficiency and avoids the formation of undesired side products. Crucial factors for product formation are the availability of NADPH and the amount of active enzyme in the cells. The efficiency of the reaction is comparable to typical whole-cell biotransformations in E. coli. Under optimized conditions, a solution of 100 mg prochiral 2-methylmaleimide was reduced to optically pure 2-methylsuccinimide (99 % ee, 80 % yield of isolated product). High product yields and excellent optical purities demonstrate the synthetic usefulness of light-catalyzed whole-cell biotransformations using recombinant cyanobacteria.
