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
Photocatalytic Oxidations of Lactams and N-Acylamines
Pavlik, James W.,Tantayanon, Supawan
, p. 6755 - 6757 (1981)
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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.
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.
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.
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.
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Vember et al.
, (1967)
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Photo-Fries-type rearrangement of cyclic enamides. An efficient route to structurally diverse five-membered enaminones
Furman, Bart?omiej,Szcze?niak, Piotr
supporting information, p. 1898 - 1901 (2022/02/19)
A simple, efficient and user-friendly protocol for the preparation of structurally diverse enaminones from enamides has been developed. The strategy is based on a photo-induced intramolecular Fries-type rearrangement. The photochemical transformation proceeds under mild reaction conditions, applies to a broad substrate range, is highly economic, and limits the amount of waste produced. The proposed methodology was used as a key step in the synthesis of dihydrojasmone an important fragrance compound.
Rapid and one-pot synthesis of tri- to tetradeca-deutero nicotines
Chandrasekhar, Srivari,Gouthami, Pashikanti,Karteek Goud, Gadela,Mainkar, Prathama S.
, (2020/02/11)
A very rapid one-pot synthesis of (±)-nicotine and tri- to tetradeca-deuterated nicotines is described where the synthetic sequence requires less than 4 h.
