25291-41-2Relevant academic research and scientific papers
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.
SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF
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Paragraph 00506, (2018/08/03)
Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.
Substituted benzimidazole derivatives
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Paragraph 0042; 0044; 0045; 0142, (2018/01/09)
The invention belongs to the field of pharmaceutical chemistry, particularly relates to substituted benzimidazole derivatives as well as a preparation method and pharmaceutical composition thereof and further relates to an application of the substituted b
Alcohols as electrophiles: Iron-catalyzed Ritter reaction and alcohol addition to alkynes
Jefferies, Latisha R.,Cook, Silas P.
supporting information, p. 4204 - 4207 (2014/06/09)
A simple, iron-based catalytic system allows for a straightforward method for the synthesis of primary, secondary, and tertiary amides. The system also allows the addition of benzyl alcohols across phenylacetylene to produce substituted phenyl ketones. This transformation improves and expands the substrate scope beyond that previously reported and proceeds under mild reaction conditions, tolerating air and moisture.
Tandem synthesis of amides and secondary amines from esters with primary amines under solvent-free conditions
Lee, Jeongbin,Muthaiah, Senthilkumar,Hong, Soon Hyeok
, p. 2653 - 2660 (2014/09/17)
An iridium(III)-catalyzed tandem synthesis of amides and amines from esters under solvent-free conditions is described. A commercially available iridium(III) complex, [Cp*IrCl2]2, with sodium acetate showed the best activity for the synthesis of amides and secondary amines. The amide was formed by ester-amide exchange which generates an alcohol in situ which is subsequently transformed to a secondary amine via hydrogen autotransfer. This synthetic protocol with high atom economy generates water as the sole by-product and can afford amides and amines from various esters in a one-pot reaction, expanding the synthetic versatility of ester transformations.
Isopropenyl acetate, a remarkable, cheap and acylating agent of amines under solvent- and catalyst-free conditions: A systematic investigation
Pelagalli, Romina,Chiarotto, Isabella,Feroci, Marta,Vecchio, Stefano
supporting information; experimental part, p. 2251 - 2255 (2012/09/08)
Isopropenyl acetate was proved to be an efficient reagent for acetylation of amine in the absence of solvent and catalyst. The corresponding acetamides were obtained in very high yields without any purification.
Intermolecular ritter-type C-H amination of unactivated sp3 carbons
Michaudel, Quentin,Thevenet, Damien,Baran, Phil S.
experimental part, p. 2547 - 2550 (2012/04/04)
Intermolecular Ritter-type C-H amination of unactivated sp3 carbons has been developed. This new reaction proceeds under mild conditions using readily available reagents and an inexpensive source of nitrogen (acetonitrile). A broad scope of substrates can be aminated with this method since many functional groups are tolerated. This reaction also allows for the direct, innate C-H amination of a variety of hydrocarbons such as cyclohexane without the need of prefunctionalization or installation of a directing group.
Safe and efficient ritter reactions in flow
Brandt, Johan C.,Elmore, Simon C.,Robinson, Richard I.,Wirth, Thomas
experimental part, p. 3099 - 3103 (2011/02/25)
Efficient mixing, temperature control and small environmental exposures allow reactions carried out in microfluidic de-vices to perform superior to their batch-type counterparts in conventional flasks. The Ritter reaction has been optimised for flow conditions leading to short reaction times and higher yields and also is more feasible with regards to safety, productivity and tolerance towards substrate functionalities.
PROTEIN KINASE INHIBITORS
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Page/Page column 10, (2010/07/04)
The present invention provides a compound of formula (I): or a pharmaceutically acceptable salt thereof which is useful in the treatment of cell proliferative diseases.
