1124-53-4Relevant articles and documents
Furan-based acetylating agent for the chemical modification of proteins
De, Sudipta,Kumar, Tarun,Bohre, Ashish,Singh, Laishram R.,Saha, Basudeb
, p. 791 - 796 (2015)
We have synthesized a furan-based acetylating agent, 2,5-bisacetoxymethylfuran (BAMF) from carbohydrate derived 5-hydroxymethylfurfural (HMF) and studied its acetylation activity with amines and cytochrome c. The results show that BAMF can modify proteins in biological conditions without affecting their structure and function. The modification of cytochrome c with BAMF occurred through the reduction of heme center, but there was no change in the coordination property of iron and the tertiary structure of cytochrome c. Further analysis using MALDI-TOF-MS spectrometer suggests that BAMF selectively targeted lysine amino acid of cytochrome c under our experimental conditions. Kinetics study revealed that the modification of cytochrome c with BAMF took place at faster rates than aspirin.
Ruthenium-supported catalysts for the stereoselective hydrogenation of paracetamol to 4-trans-acetamidocyclohexanol: Effect of support, metal precursor, and solvent
Bachiller-Baeza,Guerrero-Ruiz,Rodriguez-Ramos
, p. 439 - 445 (2005)
The influence of the support, the metal precursor, and the solvent on the selective hydrogenation of paracetamol (4-acetamidophenol) was studied over supported ruthenium catalysts. The catalysts supported on the oxidic supports Al2O3 and SiO2 gave the best results in terms of activity, selectivity for the acetamidocyclohexanols (99%), and stereoselectivity for the trans isomer (53 and 46%, respectively). Carbon-supported catalysts produced larger amounts of secondary compounds, mainly N-cyclohexylacetamide, which was derived from the hydrogenolysis reaction of the OH group. The use of a chloride precursor resulted in the enhancement of the formation of N-cyclohexylacetamide and partially hydrogenated products; the stereoselectivity also increased. Moreover, because of the acidity caused by residual Cl, condensation led to oligomers of paracetamol. In spite of the decrease in the selectivity for cyclohexanol derivatives when the more polar solvent ethanol was used instead of isopropanol or tetrahydrofuran the stereoselectivity for the trans isomer increased from 30 to 38%. The results confirm that the factors studied affect the mode of adsorption of the molecule of paracetamol on the catalyst in different ways. These effects determine the product distribution and the selectivity of the reaction.
Colloid and nano-sized catalysts in organic synthesis: X. Synthesis of carboxamides by direct amidation of carboxylic acids and transamidation catalyzed by colloid copper
Mokhov,Popov, Yu. V.,Budko
, p. 820 - 826 (2015)
Abstract It was found that in the presence of colloid copper the direct amidation of some carboxylic acids with primary and secondary amines in benzene with azeotropic distillation of water became possible. The catalyst was proven to be suitable also for transamidation reaction of a number of carboxylic acid amides under mild conditions in solvent-free conditions.
Amidomercuration; a New and Regiospecific Addition of Amides to Olefins
Barluenga, Jose,Jimenez, Carmen,Najera, Carmen,Yus, Miguel
, p. 670 - 671 (1981)
The reaction of olefins with anhydrous mercury(II) nitrate in the presence of primary amides leads, after in situ alkaline sodium borohydride reduction, to the corresponding N-substituted amides; this procedure provides a new, convenient method for the Markovnikov amidation of carbon-carbon double bonds.
Brown,Kurek
, p. 5647 (1969)
AN IMPROVED MODIFICATION OF RITTER REACTION
Martinez, A. Garcia,Alvarez, A. Martinez,Vilar, E. Teso,Fraile, A. Garcia,Hanack, M.,Subramanian, L. R.
, p. 581 - 582 (1989)
The reaction of alcohols 1 with trifluoromethane sulfonic anhydride (Tf2O) in dichloromethane in presence of a 2:1 excess of nitriles 3 affords the corresponding amides 5 in good yields.
Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)─Boron Lewis Acid Catalysis
Narobe, Rok,Murugesan, Kathiravan,Schmid, Simon,K?nig, Burkhard
, p. 809 - 817 (2022/01/15)
Recent years have witnessed important progress in synthetic strategies exploiting the reactivity of carbocations via photochemical or electrochemical methods. Yet, most of the developed methods are limited in their scope to certain stabilized positions in molecules. Herein, we report a metal-free system based on the iodine (I/III) catalytic manifold, which gives access to carbenium ion intermediates also on electronically disfavored benzylic positions. The unusually high reactivity of the system stems from a complexation of iodine (III) intermediates with BF3. The synthetic utility of our decarboxylative Ritter-type amination protocol has been demonstrated by the functionalization of benzylic as well as aliphatic carboxylic acids, including late-stage modification of different pharmaceutical molecules. Notably, the amination of ketoprofen was performed on a gram scale. Detailed mechanistic investigations by kinetic analysis and control experiments suggest two mechanistic pathways.
Tropylium-promoted Ritter reactions
Doan, Son H.,Hussein, Mohanad A.,Nguyen, Thanh Vinh
supporting information, p. 8901 - 8904 (2021/09/10)
The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuableN-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.
Metal-free Photocatalytic Intermolecular anti-Markovnikov Hydroamination of Unactivated Alkenes
Li, Juncheng,Wang, Ting,Zhao, Gaoyuan
supporting information, p. 2650 - 2654 (2021/06/25)
The development of photocatalytic intermolecular hydroamination reaction between N-aminated dihydropyridines and unactivated alkenes is reported. Metal-free co-catalysts, rhodamine 6G and thiophenol, in presence of visible light are used to initiate the process. The transformation shows a broad substrate scope, both alkenes and amidyl radical can act as coupling partners. The radical strategy provides excellent anti-Markovnikov selectivity and regioselectivity in diene substrates.
