534-84-9Relevant academic research and scientific papers
Mechanistic studies on counter-ionic effects of camphorsulfonate-based ionic liquids on kinetics, thermodynamics and stereoselectivity of β-amino carbonyl compounds
Hamzah, Ahmad Sazali,Jabeen, Erum,Leveque, Jean-Marc,Sardar, Sabahat,Wilfred, Cecilia Devi
, (2020/10/08)
Catalysis is important in various applications of organic chemistry and its output product control for stereoselective compounds is outrageous. Establishment of experimental facts of stereoselective compounds from catalysis and their validation using theoretical evidences is the key to understand various mechanisms of optically active compounds. A family of new ionic liquids (ILs) with various imidazolium cations and camphorsulfonate anion as environmentally benign liquid salts have been synthesized and deployed for catalysis of β-amino carbonyl compounds. The products were formed using ILs as a homogeneous catalyst with excellent product yield and diastereoselectivity. The effect of counter ions, Hammett acidity and viscosity of ILs along with solvent and temperature are explored in terms of reaction kinetics and product yields. Density functional theory (DFT) was used to investigate thermodynamical study of mechanistic pathway of the reaction. The DFT calculations predicted that the catalysis mechanism involved both counterions of the IL. Moreover, it is evidenced that the syn-pathway required lower activation energy while anti-pathway led to thermodynamically stable product. This study explores new avenues for using ILs as potential homogeneous catalysts for the production of stereoselective species.
Study of 2-(piperidine-1-ylmethyl)cyclohexanamine structure synthesis based on oxime protected compounds in mannich mechanism
Taheri, Milad,Soleymani, Reza,Hosn, Bita,Rajabzadeh, Halimeh,Darvish, Mohammad Raouf
experimental part, p. 387 - 397 (2012/10/07)
2-(piperidine-1 -ylmethyl)cyclohexanone (PMC), 2-(piperidine-1 -ylmethyl)cyclohexanone oxime (PMCO) structures and also 2-(piperidirte-1- ylmethyl) cyclohexan amine (PMCA) structure were extracted using experimental methods of Mannich reaction, based on o
Carbamoyloximes as novel non-competitive mGlu5 receptor antagonists
Galambos, Janos,Wagner, Gabor,Nogradi, Katalin,Bielik, Attila,Molnar, Laszlo,Bobok, Amrita,Horvath, Attila,Kiss, Bela,Kolok, Sandor,Nagy, Jozsef,Kurko, Dalma,Bakk, Monika L.,Vastag, Monika,Saghy, Katalin,Gyertyan, Istvan,Gal, Krisztina,Greiner, Istvan,Szombathelyi, Zsolt,Keser, Gyoergy M.,Domany, Gyoergy
scheme or table, p. 4371 - 4375 (2010/10/02)
Hit-to-lead optimization of a HTS hit led to new carbamoyloxime derivatives. After identification of an advanced hit (8d) the CYP enzyme inhibitory activity of this class of compounds was successfully eliminated. Systematic exploration of different parts of the advanced hit led us to some promising lead compounds with mGluR5 affinities comparable to that of MPEP.
The mechanistic study and synthetic applications of the base treatment in the ozonolytic reactions
Hon, Yung-Son,Lin, Sheng-Wun,Lu, Ling,Chen, Yao-Jung
, p. 5019 - 5034 (2007/10/02)
The E1cb mechanism is the overwhelming process in the reaction of bases and ozonides. As a quenching agent in the ozonolysis of a variety of alkenes, the reactions involving triethylamine often gave better yields and proceeded faster than those involving methyl sulfide. On the other hand, in the presence of 4 A molecular sieves, the secondary amines reacted with mono- and 1,1-di-substituted ozonides to afford the reductive amination products in high yields. The formation of ammonium formate in the reaction mixture also supported the E1cb mechanism in the reaction of ozonide and amine.
The reactions of the ozonides with secondary amines: An efficient and novel way to prepare tertiary amine from mono- and 1,1-di-substituted alkenes via corresponding ozonides
Hon, Yung-Son,Lu, Ling
, p. 5309 - 5312 (2007/10/02)
The ozonolysis of mono- and 1,1-di-substituted olefins followed by treatment with secondary amines in the presence of 4A, molecular sieves to give the corresponding tertiary amine in high yields. This transformation involved four sequential reactions in the same flask.
Benzotriazole-assisted synthesis of novel mannich bases from ketones and diverse aldehydes
Katritzky, Alan R.,Harris, Philip A.
, p. 987 - 996 (2007/10/02)
A wide variety of β-amino ketones are prepared in moderate to good yields by the reaction of the lithium enolates of cyclohexanone, acetophenone, α-tetralone and camphor with the readily available adducts from an aldehyde or ketone, an amine and benzotriazole. Some diastereoselectivity is observed when the benzotriazole adduct is derived from benzaldehyde.
