81404-55-9Relevant articles and documents
Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in theN-dimethylation synthesis of amines under mild conditions
Liu, Jianguo,Ma, Longlong,Song, Yanpei,Zhang, Mingyue,Zhuang, Xiuzheng
supporting information, p. 4604 - 4617 (2021/06/30)
The development of Earth-abundant, reusable and non-toxic heterogeneous catalysts to be applied in the pharmaceutical industry for bio-active relevant compound synthesis remains an important goal of general chemical research.N-methylated compounds, as one of the most essential bioactive compounds, have been widely used in the fine and bulk chemical industries for the production of high-value chemicals. Herein, an environmentally friendly and simplified method for the preparation of graphene encapsulated Ni/NiO nanoalloy catalysts (Ni/NiO@C) was developed for the first time, for the highly selective synthesis ofN-methylated compounds using various functional amines and aldehydes under easy to handle, and industrially applicable conditions. A large number of primary and secondary amines (more than 70 examples) could be converted to the correspondingN,N-dimethylamines with the participation of different functional aldehydes, with an average yield of over 95%. A gram-scale synthesis also demonstrated a similar yield when compared with the benchmark test. In addition, it was further proved that the catalyst could easily be recycled because of its intrinsic magnetism and reused up to 10 times without losing its activity and selectivity. Also, for the first time, the tandem synthesis ofN,N-dimethylamine products in a one-pot process, using only a single earth-abundant metal catalyst, whose activity and selectivity were more than 99% and 94%, respectively, for all tested substrates, was developed. Overall, the advantages of this newly developed method include operational simplicity, high stability, easy recyclability, cost-effectiveness of the catalyst, and good functional group compatibility for the synthesis ofN-methylation products as well as the industrially applicable tandem synthesis process.
Palladium meditated CPhenyl-H bond activation of 2-furylimines versus tert-2-furylbenzylamines
Hu, Zhao-Xia,Ma, Nan,Zhang, Jin-Hua,Hu, Wen-Ping,Wang, Hong-Xing
, p. 30 - 35 (2015/01/09)
The reactions of 2-furylimines 2a-f and Na2PdCl4 in the presence of NaOAc at 8-10°C result in nitrogen-palladium coordinated complexes 3a-f. Reduction of 2d-f with NaBH4 followed by N-methylation leads to the corresponding tert-2-furylbenzylamines 5a-c. Treatment of 5a-c with Na2PdCl4 at the same reaction condition as mentioned above affords palladacycles 6a-c where the Pd atoms connect to the phenyl ring rather than the furyl ring. The fact that 5a-c are more active than 2d-f in CPhenyl-H bond activation implies that the electron density of C10 or C8 atom in former is higher than those in latter. Compounds 3a-f, 5a-c, 6a-c were identified by elemental analysis, IR and NMR. In addition, the structures of 3b, 3f and 6c were also confirmed by their single crystal X-ray diffractions.
SYNTHETIC BIOREGULATORS OF POLY-CIS CAROTENOID BIOSYNTHESIS
Poling, Stephen M.,Hsu, Wan-Jean,Yokoyama, Henry
, p. 601 - 604 (2007/10/02)
Seventeen new bioregulators were synthesized and tested for their ability to induce the biosynthesis of poly-cis carotenes in the flavedo of Marsh white seedless grapefruit.The effects of these new bioregulators are the same as that of the previously reported dibenzylamines, but several of the new compounds are more effective and cause the accumulation of up to 162 μg/g dry wt of poly-cis carotenes in the flavedo as compared to the maximum of 74 μg/g dry wt observed previously.The compounds tested were substituted N-benzyl furfurylamines, N-benzyl, N-methyl furfurylamines and N-alkyl , N-methyl benzylamines.They demonstrate the ability of tertiary as well as secondary amines to stimulate the formation of poly-cis carotenes.The interaction of N-(4-bromobenzyl) furfurylamine, one of the more effctive of the new compounds, with lycopene and β-carotene inducers is also reported.Key Word Index - Citrus paradisi; Rutaceae; Marsh white seedles grapefruit; carotenoid biosynthesis; bioregulators; secondary amines; poly-cis carotenoids; prolycopene.
