5813-89-8Relevant articles and documents
Lead derivatization of ethyl 6-bromo-2-((dimethylamino)methyl)-5-hydroxy-1-phenyl-1H-indole-3-carboxylate and 5-bromo-2-(thiophene-2-carboxamido) benzoic acid as FabG inhibitors targeting ESKAPE pathogens
Varakala, Saiprasad Dasugari,Reshma, Rudraraju Srilakshmi,Schnell, Robert,Dharmarajan, Sriram
, (2021/11/26)
Our previous studies on FabG have identified two compounds 5-bromo-2-(thiophene-2-carboxamido) benzoic acid (A) and ethyl 6-bromo-2-((dimethylamino)methyl)-5-hydroxy-1-phenyl-1H-indole-3-carboxylate(B) as best hits with allosteric mode of inhibition. FabG is an integral part of bacterial fatty acid biosynthetic system FAS II shown to be an essential gene in most ESKAPE Pathogens. The current work is focussed on lead expansion of these two hit molecules which ended up with forty-three analogues (twenty-nine analogues from lead compound A and fourteen compounds from lead compound B). The enzyme inhibition studies revealed that compound 15 (effective against EcFabG, AbFabG, StFabG, MtFabG1) and 19 (inhibiting EcFabG and StFabG) had potency of broad-spectrum inhibition on FabG panel.
Mechanochemical synthesis of half-sandwich iridium/rhodium complexes with 8-hydroxyquinoline derivatives ligands
Jia, Wei-Guo,Li, Xiao-Dong,Zhi, Xue-Ting,Zhong, Rui
, (2022/01/19)
Mechanochemistry provides a rapid, efficient route to half-sandwich iridium and rhodium complexes from [MCp*(μ-Cl)Cl]2 (M = Ir, Rh) and 8-hydroxyquinoline-2-carbaldehyde without the need for Schlenk manipulation, inert gas protection, or dry solvents. Furthermore, post-synthetic modification of the half-sandwich metal complexes has been carried out via a mechanochemical Wittig reaction between half-sandwich metal complex and phosphorus ylide. All complexes were fully characterized by 1H and 13C NMR spectra, infrared spectroscopy, mass spectrometry, and single-crystal X-ray diffraction method. The half-sandwich rhodium complexes exhibited high catalytic activity towards the amide synthesis between aldehyde and hydroxylamine hydrochloride (NH2OH·HCl) with a broad functional group tolerance.
Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes
Schmidt-R?ntsch, Till,Verplancke, Hendrik,Lienert, Jonas N.,Demeshko, Serhiy,Otte, Matthias,Van Trieste, Gerard P.,Reid, Kaleb A.,Reibenspies, Joseph H.,Powers, David C.,Holthausen, Max C.,Schneider, Sven
, (2022/01/20)
C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.
Sustainable synthesis of drug intermediates via simultaneous utilization of carbon monoxide and ammonia over Pd@La-MOF
Bhattacharya, Sumantra,Bordoloi, Ankur,Das, Subhasis,Gazi, Jahiruddin,Islam, Sk Manirul,Prasad, V. V. D. N.,Sengupta, Manideepa
, (2022/03/14)
Mitigation of carbon monoxide and ammonia to valuable primary aromatic amides is an imperative approach to control the environmentally harmful emissions thereby infusing towards sustainability. Designing of nanostructured catalyst for direct access to the synthetically valuable primary aromatic and heteroaromatic amides via carbonylative amination of aryl halides is always demanding since nano materials can bridge the gap between homogeneous and heterogeneous catalysis thus preserving the desirable attributes of both the systems towards sustainable catalysis. Herein, microwave assisted fabrication of highly uniform Pd NPs (3,4 nm) over La-MOFs has been performed and utilized efficiently for ligand free carbonylative amination of aryl iodides with carbon monoxide and ammonia. Moderate to high yields of benzamide derivatives, salicylamide, a drug having analgesic and antipyretic properties were achieved. The unsaturated metal sites in the MOF via synergistic mode of σ and π bonding binds with CO, which significantly enhances the catalytic activity of MOF-composite unlike other supported Pd NPs. DFT confirms the growth of pristine Pd13 cluster within the framework, as active metal center for the carbonylative amination.
Single-pot tandem oxidative/C-H modification amidation process using ultrasmall PdNP-encapsulated porous organosilica nanotubes
Gholipour, Behnam,Liu, Xiao,Rostamnia, Sadegh,Zonouzi, Afsaneh
, p. 4276 - 4287 (2022/02/16)
Herein, we studied a single-pot method with a dual catalysis process towards the conversion of primary aromatic alcohols to amides using ultrasmall PdNPs of controlled uniform size (1.8 nm) inside hybrid mesoporous organosilica nanotubes (MO-NTs). The cat
A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides
Bartling, Stephan,Beller, Matthias,Chandrashekhar, Vishwas G.,Jagadeesh, Rajenahally V.,Rabeah, Jabor,Rockstroh, Nils,Senthamarai, Thirusangumurugan
supporting information, p. 508 - 531 (2022/02/11)
Functionalized (hetero)aromatic compounds are indispensable chemicals widely used in basic and applied sciences. Among these, especially aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides represent valuable fine and bulk chemicals, which are used in chemical, pharmaceutical, agrochemical, and material industries. For their synthesis, catalytic aerobic oxidation of alcohols constitutes a green, sustainable, and cost-effective process, which should ideally make use of active and selective 3D metals. Here, we report the preparation of graphitic layers encapsulated in Co-nanoparticles by pyrolysis of cobalt-piperazine-tartaric acid complex on carbon as a most general oxidation catalyst. This unique material allows for the synthesis of simple, functionalized, and structurally diverse (hetero)aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides from alcohols in excellent yields in the presence of air.
Cu(II)-promoted oxidative C-N bond cleavage of N-benzoylamino acids to primary aryl amides
Zhou, Liandi,Liu, Wei,Zhao, Yongli,Chen, Junmin
, p. 52 - 62 (2021/02/06)
A novel protocol for CuCl2-promoted oxidative C-N bond cleavage of N-benzoyl amino acids was developed. It is the first example of using accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl amides via CuCl2-promoted oxidative C-N bond cleavage reaction. The present protocol shows excellent functional group tolerance and provides an alternative method for the synthetic of primary aryl amides in 84-96% yields.
Mechanochemical Synthesis of Primary Amides
Gómez-Carpintero, Jorge,Sánchez, J. Domingo,González, J. Francisco,Menéndez, J. Carlos
, p. 14232 - 14237 (2021/10/20)
Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.
Half-Sandwich Iridium Complexes Based on β-Ketoamino Ligands: Preparation, Structure, and Catalytic Activity in Amide Synthesis
Wang, Yang,Guo, Wen,Guan, Ai-Lin,Liu, Shuang,Yao, Zi-Jian
, p. 11514 - 11520 (2021/07/31)
A series of β-ketoamino-based N,O-chelate half-sandwich iridium complexes with the general formula [Cp*IrClL] have been prepared in good yields. These air-insensitive iridium complexes showed desirable catalytic activity in an amide preparation under mild conditions. A number of amides with diverse substituted groups were furnished in a one-pot reaction with good-to-excellent yields through an amidation reaction of NH2OH·HCl with aldehydes in the presence of these iridium(III) precursors. The excellent catalytic activity, mild reaction conditions, and broad substrate scope gave this type of iridium catalyst potential for use in industry. All of the obtained iridium complexes were well characterized by different spectroscopy techniques. The exact molecular structure of complex 3 has been confirmed by single-crystal X-ray analysis.
Nano-construction of CuO nanorods decorated with g-C3N4 nanosheets (CuO/g-C3N4-NS) as a superb colloidal nanocatalyst for liquid phase C[sbnd]H conversion of aldehydes to amides
Mohammadi, Robabeh,Gholipour, Behnam,Alamgholiloo, Hassan,Rostamnia, Sadegh,Mohtasham, Hamed,Zonouzi, Afsaneh,Ramakrishna, Seeram,Shokouhimehr, Mohammadreza
, (2021/04/27)
Herein, we describe an intelligent strategy to fabricate nanosheets of graphitic carbon nitride (g-C3N4) decorated with nanorods copper oxide (CuO NRs). Then, the catalytic activity of CuONRs/g-C3N4-NS was developed for the synthesis of primary amides in water. The morphology of CuO and its synergetics effect with nanosheets g-C3N4 a major role in the yield of products. Furthermore, hydroxylamine hydrochloride (NH2OH·HCl) due to availability and affordability was used as a suitable substitute for ammonia source. The findings demonstrate that this layer nanostructure is a superb catalyst for converting various derivatives of aldehyde to their corresponding amides. The current protocol can be useful criterion in the synthesis and stabilization of metal oxides and provides new insight in organic transformation.
