86010-67-5Relevant 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.
Environmentally benign decarboxylative: N-, O-, and S-Acetylations and acylations
Ghosh, Santanu,Purkait, Anisha,Jana, Chandan K.
supporting information, p. 8721 - 8727 (2020/12/30)
An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically pure acetylated products without the requirement of work-up and any chromatography. This journal is
Dichotomy of Atom-Economical Hydrogen-Free Reductive Amidation vs Exhaustive Reductive Amination
Kolesnikov, Pavel N.,Usanov, Dmitry L.,Muratov, Karim M.,Chusov, Denis
supporting information, p. 5657 - 5660 (2017/10/25)
Rh-catalyzed one-step reductive amidation of aldehydes has been developed. The protocol does not require an external hydrogen source and employs carbon monoxide as a deoxygenative agent. The direction of the reaction can be altered simply by changing the solvent: reaction in THF leads to amides, whereas methanol favors formation of tertiary amines.
Designing of thermally stable amide functionalized benzimidazolium perchlorate ionic liquid for transamidation of primary carboxamides
Muskawar, Prashant Narayan,Thenmozhi,Bhagat, Pundlik Rambhau
, p. 158 - 167 (2015/09/28)
In the present work, we have designed and synthesized a thermally stable catalyst based on functionalized benzimidazolium perchlorate ionic liquid and tested its efficacy towards metal free and solvent free transamidation of amides and amines. The ionic liquid comprising the perchlorate ion has shown remarkably better activity than those which contain other anions and accordingly a plausible mechanism for the catalytic activity is arrived. The developed catalytic system has shown excellent activity towards the transamidation of alicyclic and aromatic amines with acetamide, benzamide and p-nitrobenzamide under mild conditions. Furthermore, the transamidation of nicotinamide with benzylamine in presence of the ionic liquid catalyst was found to occur with very good yields and thus provides a facile route for the synthesis of pharmaceutically significant compounds. The catalyst has exhibited very good thermal stability upto 203 °C and very good recyclability upto 5 runs without significant loss in its activity.
L-Proline: An efficient catalyst for transamidation of carboxamides with amines
Rao, Sadu Nageswara,Mohan, Darapaneni Chandra,Adimurthy, Subbarayappa
supporting information, p. 1496 - 1499 (2013/06/27)
In the presence of a catalytic amount of l-proline (10 mol %), transamidations of carboxamides with amines were achieved under solvent-free conditions. The transamidation process is compatible with a wide range of amines.
Pyrano-[2,3b]-pyridines as potassium channel antagonists
Finlay, Heather J.,Lloyd, John,Nyman, Michael,Conder, Mary Lee,West, Tonya,Levesque, Paul,Atwal, Karnail
, p. 2714 - 2718 (2008/12/21)
The design and synthesis of a series of highly functionalized pyrano-[2,3b]-pyridines is described. These compounds were assayed for their ability to block the IKur channel encoded by the gene hKV1.5 in patch-clamped L-929 cells. Six of the compounds in this series showed sub-micromolar activity, the most potent being 4-(4-ethyl-benzenesulfonylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3b]-pyridine-6-carboxylic acid ethyl-phenyl-amide with an IC50 of 378 nM.
Benzyl amide-ketoacid inhibitors of HIV-integrase
Walker, Michael A.,Johnson, Timothy,Naidu, B. Narasimhulu,Banville, Jacques,Remillard, Roger,Plamondon, Serge,Martel, Alain,Li, Chen,Torri, Albert,Samanta, Himadri,Lin, Zeyu,Dicker, Ira,Krystal, Mark,Meanwell, Nicholas A.
, p. 4886 - 4890 (2008/02/13)
Integrase is one of three enzymes expressed by HIV and represents a validated target for therapy. Previous reports have demonstrated that the diketoacid-based chemotype is a useful starting point for the design of inhibitors of this enzyme. In this study, one of the ketone groups is replaced by a benzylamide resulting in a new potent chemotype. A preliminary SAR study is carried out to investigate the substitution requirements on the phenyl ring and methylene group of the benzylamide.
