34274-02-7Relevant articles and documents
Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1 H)-ones
Liu, Yongzhu,Qi, Xinxin,Wu, Xiao-Feng
, p. 13824 - 13832 (2021/10/12)
A palladium-catalyzed straightforward procedure for the synthesis of 3-arylquinolin-2(1H)-ones has been developed. The synthesis proceeds through a palladium-catalyzed reductive aminocarbonylation reaction of benzylic ammonium triflates with o-nitrobenzaldehydes, and a wide range of 3-arylquinolin-2(1H)-ones was obtained in moderate to good yields with very good functional group compatibility.
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.
Synthesis of tertiary amines by direct Br?nsted acid catalyzed reductive amination
Hussein, Mohanad A.,Dinh, An H.,Huynh, Vien T.,Nguyen, Thanh Vinh
supporting information, p. 8691 - 8694 (2020/08/21)
Tertiary amines are ubiquitous and valuable compounds in synthetic chemistry, with a wide range of applications in organocatalysis, organometallic complexes, biological processes and pharmaceutical chemistry. One of the most frequently used pathways to synthesize tertiary amines is the reductive amination reaction of carbonyl compounds. Despite developments of numerous new reductive amination methods in the past few decades, this reaction generally requires non-atom-economic processes with harsh conditions and toxic transition-metal catalysts. Herein, we report simple yet practical protocols using triflic acid as a catalyst to efficiently promote the direct reductive amination reactions of carbonyl compounds on a broad range of substrates. Applications of this new method to generate valuable heterocyclic frameworks and polyamines are also included.
Facile synthesis of controllable graphene-co-shelled reusable Ni/NiO nanoparticles and their application in the synthesis of amines under mild conditions
Cui, Zhibing,Liu, Jianguo,Liu, Qiying,Ma, Longlong,Singh, Thishana,Wang, Chenguang,Wang, Nan,Zhu, Yuting
supporting information, p. 7387 - 7397 (2020/11/19)
The primary objective of many researchers in chemical synthesis is the development of recyclable and easily accessible catalysts. These catalysts should preferably be made from Earth-abundant metals and have the ability to be utilised in the synthesis of pharmaceutically important compounds. Amines are classified as privileged compounds, and are used extensively in the fine and bulk chemical industries, as well as in pharmaceutical and materials research. In many laboratories and in industry, transition metal catalysed reductive amination of carbonyl compounds is performed using predominantly ammonia and H2. However, these reactions usually require precious metal-based catalysts or RANEY nickel, and require harsh reaction conditions and yield low selectivity for the desired products. Herein, we describe a simple and environmentally friendly method for the preparation of thin graphene spheres that encapsulate uniform Ni/NiO nanoalloy catalysts (Ni/NiO?C) using nickel citrate as the precursor. The resulting catalysts are stable and reusable and were successfully used for the synthesis of primary, secondary, tertiary, and N-methylamines (more than 62 examples). The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, and H2 under very mild industrially viable and scalable conditions (80 °C and 1 MPa H2 pressure, 4 h), offering cost-effective access to numerous functionalized, structurally diverse linear and branched benzylic, heterocyclic, and aliphatic amines including drugs and steroid derivatives. We have also demonstrated the scale-up of the heterogeneous amination protocol to gram-scale synthesis. Furthermore, the catalyst can be immobilized on a magnetic stirring bar and be conveniently recycled up to five times without any significant loss of catalytic activity and selectivity for the product.
The sustainable heterogeneous catalytic reductive amination of lignin models to produce aromatic tertiary amines
Zhang, Haigang,Tong, Xinli,Liu, Zonghui,Wan, Jun,Yu, Linhao,Zhang, Zhenya
, p. 5396 - 5400 (2018/11/20)
A novel heterogeneous catalytic process for efficient reductive amination is developed in the presence of heterogeneous zirconium-based catalysts, in which N,N-dimethylformamide is used as the solvent, low-molecular-weight amine source and reductant. Aromatic tertiary amines have been produced from lignin-derived aromatic aldehydes via the mild Leuckart reaction with ZrO2 or ZrO(OH)2 as catalysts, for instance, a 95.8% yield of N,N-dimethyl-1-(3,4,5-trimethoxyphenyl)methanamine in a 100% selectivity is obtained from the reductive amination of 3,4,5-trimethoxybenzaldehyde under mild conditions.
Direct Synthesis of N,N-Dimethylated and β-Methyl N,N-Dimethylated amines from nitriles using methanol: Experimental and computational studies
Paul, Bhaskar,Shee, Sujan,Panja, Dibyajyoti,Chakrabarti, Kaushik,Kundu, Sabuj
, p. 2890 - 2896 (2018/04/14)
Direct and selective synthesis of N,N-dimethylated amines from nitriles using methanol as C1 building blocks is reported using an air- and moisture-stable ruthenium complex. Following this process, various aromatic as well as aliphatic nitriles were converted to the corresponding N-methylated amines. Interestingly, tandem C-methylation as well as N-methylation was achieved by introducing multiple methyl groups. The practical aspect of this process was revealed by preparative-scale reactions with different nitriles and the synthesis of anti-allergic drug "avil". Several kinetic experiments and detailed DFT calculations were carried out to understand the mechanism of this process.
Lewis Acid-Catalyzed Reductive Amination of Aldehydes and Ketones with N,N-Dimethylformamide as Dimethylamino Source, Reductant and Solvent
Yang, Luo,Lin, Jie,Kang, Lei,Zhou, Wang,Ma, Da-You
supporting information, p. 485 - 490 (2018/01/15)
A practical zinc acetate dihydrate-catalyzed reductive amination of various carbonyl compounds with N,N-dimethylformamide (DMF) as dimethylamino (Me2N) source, reductant and solvent has been developed. This reaction shows broad substrate scope,
MOF-derived cobalt nanoparticles catalyze a general synthesis of amines
Jagadeesh, Rajenahally V.,Murugesan, Kathiravan,Alshammari, Ahmad S.,Neumann, Helfried,Pohl, Marga-Martina,Radnik, J?rg,Beller, Matthias
, p. 326 - 332 (2017/09/28)
The development of base metal catalysts for the synthesis of pharmaceutically relevant compounds remains an important goal of chemical research. Here, we report that cobalt nanoparticles encapsulated by a graphitic shell are broadly effective reductive amination catalysts. Their convenient and practical preparation entailed template assembly of cobaltdiamine- dicarboxylic acid metal organic frameworks on carbon and subsequent pyrolysis under inert atmosphere.The resulting stable and reusable catalysts were active for synthesis of primary, secondary, tertiary, and N-methylamines (more than 140 examples).The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, or nitro compounds, and molecular hydrogen under industrially viable and scalable conditions, offering cost-effective access to numerous amines, amino acid derivatives, and more complex drug targets.
Convenient Synthesis of Naturally Ocurring Methoxy- and Hydroxy Phthalides
Mali, R.S.,Jagtap, P.G.,Tilve, S.G.
, p. 2641 - 2652 (2007/10/02)
A convenient method for the synthesis of phthalides (1-5), involving heteroatom directed lithiation reaction is described.
