63459-05-2Relevant articles and documents
Base-Free Oxidative Coupling of Amines and Aliphatic Alcohols to Imines over Au–Pd/ZrO2 Catalyst under Mild Conditions
Cui, Wenjing,Jia, Meilin,Sagala,Wang, Jiang
, p. 958 - 967 (2021/06/06)
Abstract: The base-free synthesis of imines from amines and aliphatic alcohols over Au–Pd alloy catalysts under ambient conditions was developed. A series of Au–Pd/ZrO2 bimetallic catalysts with varying metal loadings and Au?:?Pd molar ratios were prepared and their catalytic performance was investigated. The 3.0?wt?% Au–Pd/ZrO2 alloy catalyst with Au?:?Pd molar ratio of 1?:?1 showed the best catalytic performance. Under air atmosphere, various imines were obtained from coupling of amines and aliphatic alcohols without any additives or promoters. The performance of alloy NPs was superior to that of monometallic catalysts due to the synergistic effect which was demonstrated by TEM, XPS, and UV–Vis characterization. Our work suggested this transformation differed slightly from those reactions between amine and benzyl alcohol and a possible mechanism was proposed. Moreover, the Au–Pd/ZrO2 catalyst could be easily separated and reused for at least five successive runs with high catalytic activity.
Preparation method of pesticide intermediate 2-chloro-5-methyl pyridine
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Paragraph 0012; 0036; 0037; 0038; 0043-0045; 0050-0052, (2019/02/08)
The invention discloses a preparation method of a pesticide intermediate 2-chloro-5-methyl pyridine. The preparation method comprises the following steps: adopting benzyl chloride, ammonia water and n-propanal as a starting material, and adopting a one-pot process to synthesize an intermediate (I); then using ion exchange resin as an acid-binding agent to carry out catalytic reaction, using acetylchloride as an acylation reagent to carry out acetylation, thereby obtaining an intermediate compound (II); and leading the intermediate compound (II), DMF (Dimethyl Formamide) and solid phosgene inan organic solvent to carry out cyclizing ring-closing reaction, thereby obtaining a target compound (I). The preparation method disclosed by the invention has the beneficial effects that the materials are cheap and easy to obtain, the reaction steps are fewer, the process operation is simple, the catalyst can be repeatedly utilized, the emission of three wastes is less, the process is pollution-free and environment-friendly, the product quality is good, the yield is high and the cost is low; the preparation method is very suitable for industrial production and has extremely-strong industrialapplication value.
Rhodium-Catalyzed Enantioselective Arylation of Aliphatic Imines
Kato, Naoya,Shirai, Tomohiko,Yamamoto, Yasunori
supporting information, p. 7739 - 7742 (2016/06/09)
Chiral rhodium(I)-catalyzed highly enantioselective arylation of aliphatic N-sulfonyl aldimines with arylboronic acids has been developed. This transformation is achieved by the use of a rhodium/bis(phosphoramidite) catalyst to give enantiomerically enriched α-branched amines (up to 99 % ee). In addition, this system enables efficient synthesis of (+)-NPS R-568 and Cinacalcet which are calcimimetic agents.
Convenient modular construction of medicinally important 5-acylamino-4,5-dihydroisoxazoles featuring four elements of diversity
Kulyashova, Alexandra,Krasavin, Mikhail
supporting information, p. 4395 - 4397 (2016/09/13)
An efficient modular approach toward medicinally important 5-acylamino-4,5-isoxazolines via the 1,3-dipolar cycloaddition reaction of nitrile oxides and MCR-derived enamide building blocks is described. This approach results in isoxazolines containing four elements of diversity utilizing two practically simple synthetic operations.
A 2,3-chloro-5-chlorotrifluoromethylbenzene methylpyridinio synthetic method (by machine translation)
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Paragraph 0007, (2016/11/02)
The invention relates to a 2,3 the [...] -5 the method for synthesizing methylpyridinio [...], which belongs to the field of chemical synthesis. Traditional production 2, the 3 [...] -5 the backward [...] methylpyridinio process, flow is long, the yield is low, a large amount of the three wastes, it is difficult to control. The present invention provides a mild reaction conditions, the high yield of 2,3 the [...] -5 the method for synthesizing methylpyridinio [...]. (by machine translation)
Preparation method of 2-chloro-5-picoline
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Paragraph 0036; 0037, (2016/11/17)
The invention relates to a preparation method of 2-chloro-5-picoline. According to the method, benzyl chloride is taken as a raw material, benzaldehyde is taken as an inhibitor, ammonia is taken as an aminating agent, a product has a condensation reaction with propionaldehyde under the catalysis of an organic base, then a product has acetylation with an acetylation reagent, finally, a product performs cyclization under actions of N,N-dimethylformamide and triphosgene, and the target product 2-chloro-5-picoline is obtained through purification. The product purity is higher than or equal to 99.5%, and the total molar yield higher than 80% is realized. The preparation method of 2-chloro-5-picoline has good reaction selectivity, high yield and few three wastes, is simple to operate and facilitates industrialized production.
Synthesis of imines from amines in aliphatic alcohols on Pd/ZrO2 catalyst under ambient conditions
Cui, Wenjing,Zhaorigetu, Bao,Jia, Meilin,Ao, Wulan,Zhu, Huaiyong
, p. 2601 - 2604 (2014/01/06)
Synthesis of imines from amines and aliphatic alcohols (C 1-C6) in the presence of base on supported palladium nanoparticles has been achieved for the first time. The catalytic system shows high activity and selectivity in open air at room temperature.
Synthesis and pharmacological properties of 5-alkyl substituted nicotine analogs
Wang, Jing,Li, Xi,Yuan, Qianjia,Ren, Jiangmeng,Huang, Jin,Zeng, Bubing
, p. 2813 - 2818 (2013/08/23)
This paper describes a concise and practical route to enantiomerically enriched 5-alkyl substituted nicotine analogs. The Vilsmeier reaction was used to construct the nicotinaldehydes ring followed by the introduction of the chiral homoallylic alcohol by organic boron reagent and the cyclization of the pyrrolidine ring through the reduction of a chiral azide. 17 analogs have been synthesized and their corresponding biological activities were tested, in which compounds 10d and 10g exhibit excellent IC50 values against RD and SY-SY5Y. Copyright
Nitrile biotransformations for the synthesis of highly enantioenriched β-hydroxy and β-amino acid and amide derivatives: A general and simple but powerful and efficient benzyl protection strategy to increase enantioselectivity of the amidase
Ma, Da-You,Wang, De-Xian,Pan, Jie,Huang, Zhi-Tang,Wang, Mei-Xiang
, p. 4087 - 4091 (2008/09/20)
(Chemical Equation Presented) Biotransformations of a number of racemic β-hydroxy and β-amino nitrile derivatives were studied using Rhodococcus erythropolis AJ270, the nitrile hydratase and amidase-containing microbial whole cell catalyst, under very mild conditions. The overall enantioselectivity of nitrile biotransformations was governed predominantly by the amidase whose enantioselectivity was switched on remarkably by an O- and a N-benzyl protection group of the substrates. While biotransformations of β-hydroxy and β-amino alkanenitriles gave low yields of amide and acid products of very low enantiomeric purity, introduction of a simple benzyl protection group on the β-hydroxy and β-amino of nitrile substrates led to the formation of highly enantioenriched β-benzyloxy and β-benzylamino amides and acids in almost quantitative yield. The easy protection and deprotection operations, high chemical yield, and excellent enantioselectivity render the nitrile biotransformation a useful protocol in the synthesis of enantiopure β-hydroxy and β-amino acids.
