63452-53-9Relevant academic research and scientific papers
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
Reductive Amidation without an External Hydrogen Source Using Rhodium on Carbon Matrix as a Catalyst
Tsygankov, Alexey A.,Makarova, Maria,Afanasyev, Oleg I.,Kashin, Alexey S.,Naumkin, Alexander V.,Loginov, Dmitry A.,Chusov, Denis
, p. 112 - 117 (2019/11/28)
An efficient method for preparation of secondary amides from primary amides and aldehydes using rhodium on carbon matrix as catalyst was developed. The method does not require any external hydrogen source and carbon monoxide is used as a reducing agent. The most active rhodium catalysts were characterized by BET, TEM and XPS techniques. Unexpectedly, it was found that heterogeneous rhodium on carbon matrix works as precatalyst for homogenous active species due to leaching of rhodium to the solution. Various secondary amides were synthesized and checked for antifungal activity. 4-Methoxy-N-(4-methoxybenzyl)benzamide demonstrated promising activity against Rhizoctonia Solani.
Iridium-Catalyzed Benzylamine C-H Alkenylation Enabled by Pentafluorobenzoyl as the Directing Group
Yang, Xiao,Sun, Rui,Zhang, Chunchun,Zheng, Xueli,Yuan, Maolin,Fu, Haiyan,Li, Ruixiang,Chen, Hua
supporting information, p. 1002 - 1006 (2019/02/19)
The first iridium-catalyzed oxidative alkeynylation of benzylamines with acrylates enabled by a new directing group pentafluorobenzoyl has been developed. The reaction proceeded efficiently in the presence of silver acetate as oxidant and chlorobenzene as
Ruthenium-Catalyzed Reductive Amidation without an External Hydrogen Source
Yagafarov, Niyaz Z.,Muratov, Karim M.,Biriukov, Klim,Usanov, Dmitry L.,Chusova, Olga,Perekalin, Dmitry S.,Chusov, Denis
supporting information, p. 557 - 563 (2018/02/09)
A catalytic reaction between aldehydes and primary amides that leads to N-alkylated amides was investigated. The developed protocol employs carbon monoxide as a deoxygenative agent and, therefore, avoids the use of an external hydrogen source. Cyclopentad
Acetic acid as a catalyst for the N-acylation of amines using esters as the acyl source
Sanz Sharley, Daniel D.,Williams, Jonathan M. J.
supporting information, p. 2020 - 2023 (2017/02/15)
We report a cheap and simple method for the acetylation of a variety of amines using catalytic acetic acid and either ethyl acetate or butyl acetate as the acyl source. Catalyst loadings as low as 10 mol% afforded acetamide products in excellent yields at temperatures ranging from 80-120 °C. The methodology can also be successfully applied for the synthesis of a broad range of other amides, including the formation of formamides at 20 °C.
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.
INTEGRIN ANTAGONIST CONJUGATES FOR TARGETED DELIVERY TO CELLS EXPRESSING ALPHA-V-BETA-3
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Page/Page column 45, (2013/08/15)
The invention relates to compounds of formula (I): wherein R1, R2, and n are defined in the detailed description and claims. In particular, the present invention relates to the compounds of formula (I) for use in the manufacture and delivery of conjugated moieties such as small molecules, peptides, nucleic acids, fluorescent moieties, and polymers which are linked to alpha-V-beta-3 integrin antagonists to target cells expressing alpha-V-beta-3.
Ceric ammonium nitrate-mediated detritylation of tritylated amines
Pattanayak, Sankha,Sinha, Surajit
experimental part, p. 34 - 37 (2011/02/25)
Efficient deprotection of tritylated amines to the corresponding amines mediated by 20 mol % ceric ammonium nitrate [Ce(NH4) 2(NO3)6, CAN], 10 equiv of acetic acid and 15 equiv of water in dichloromethane is presented. This method equally worked well in the case of morpholino nucleosides.
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.
