17698-11-2

Upstream product

• 2021-28-5 ethyl dihydrocinnamate 
• 645-45-4 hydrocinnamic acid chloride 
• 501-52-0 3-Phenylpropionic acid 
• 109318-10-7 2,5-dioxopyrrolidin-1-yl 3-phenylpropanoate 
• 55628-83-6 1-(1H-imidazol-1-yl)-3-phenylpropan-1-one 
• 1185760-78-4 N-(1-Isobutoxyethoxy)-3-phenylpropionamide 
• 22426-87-5 N-benzyloxy-3-phenyl-propionamide 
• 104-53-0 3-phenyl-propionaldehyde 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 67-63-0 isopropyl alcohol 
• 443682-81-3 5,5-dimethyl-3-(2-phenylethyl)-1,4,2-dioxazole 
• 136159-65-4 (S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one 

Downstream Products

• 2038-57-5 3-Phenylpropan-1-amine 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 
• 2021-28-5 ethyl dihydrocinnamate 
• 443682-81-3 5,5-dimethyl-3-(2-phenylethyl)-1,4,2-dioxazole 
• 1943-82-4 phenethyl isocyanate 
• 1422363-62-9 C₂₅H₃₃N₃O₈ 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 64125-06-0 5-methoxycarbonylmethyl-3-phenethyl-[1,4,2]dioxazole-5-carboxylic acid methyl ester 

Relevant academic research and scientific papers

S-glycosyltransferase UGT74B1 can glycosylate both S- and O-acceptors: mechanistic insights through substrate specificity

UGT74B1 from Arabidopsis thaliana is one of the few characterized glycosyltransferases able to generate a thioglycosidic linkage in vivo, using the sulfur atom of thiohydroximate as the nucleophile in the glycosylation reaction. This critical biosynthetic

Photoinduced one-pot synthesis of hydroxamic acids from aldehydes through in-situ generated silver nanoclusters

Hydroxamic acids have attracted significant attention due to their widespread use in applied chemistry. In this report, a modified Angeli–Rimini method has been achieved via the visible light-mediated catalytic transformation of a variety of heterocyclic, aromatic and aliphatic aldehydes 1a–j to their corresponding hydroxamic acids 2a–j in 81–93% yield. The unique ability of vitamin K3 as a photoredox catalyst to expedite the development of completely new reaction mechanisms and to enable the construction of challenging carbon–nitrogen bonds has been investigated. It is shown for the first time that the vitamin K3 and aldehyde are largely responsible for rapid in situ reduction of Ag+ ions to catalytic photoluminescent Ag nanoclusters that possess a bandgap energy of 2.87?eV and are less than 2 nm in size. A mechanism for this reaction has been proposed and is supported by UV–Vis, TEM, ESI/MS, FT-IR, 1H NMR and 13C NMR analyses. The investigated method utilizes readily available reagents and produces the hydroxamic acids in high yields without the formation of side products, making it simple, practical and cost-effective.

Hydroxamates as a potent skeleton for the development of metallo-β-lactamase inhibitors

Bacterial resistance caused by metallo-β-lactamases (MβLs) has become an emerging public health threat, and the development of MβLs inhibitor is an effective way to overcome the resistance. In this study, thirteen novel O-aryloxycarbonyl hydroxamates were constructed and assayed against MβLs. The obtained molecules specifically inhibited imipenemase-1 (IMP-1) and New Delhi metallo-β-lactamase-1, exhibiting an IC50 value in the range of 0.10–18.42 and 0.23–22.33?μM, respectively. The hydroxamate 5 was found to be the most potent inhibitor, with an IC50 of 0.1 and 0.23?μM using meropenem and cefazolin as substrates. ICP-MS analysis showed that 5 did not coordinate to the Zn(II) ions at the active site of IMP-1, while the rapid dilution, thermal shift and MALDI-TOF assays revealed that the hydroxamate formed a covalent bond with the enzyme. Cytotoxicity assays indicated that the hydroxamates have low toxicity in MCF-7 cells. This work provided a potent scaffold for the development of MβLs inhibitors.

Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas

Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.

P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids

An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.

Room Temperature Benzofused Lactam Synthesis Enabled by Cobalt(III)-Catalyzed C(sp2)?H Amidation

Benzofused lactams, especially indolin-2-one and dihydroquinolin-2-one are popular structural motives in durgs and natural products. Herein, we developed a room temperature and robust synthesis of benzofused lactams through cobalt(III)-catalyzed C(sp

Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones

A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C-H bond amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an alkene can be terminated at the γ-methylene site remote from the alkene moiety. By employing 2,9-dibutyl-1,10-phenanthroline as the ligand and dioxazolones as the reagent, the amidation occurs at the γ-C(sp3)-H bonds to afford the amide products in up to 90% yield (>40 examples) with remarkable regioselectivity (up to 24:1 rr).

Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides

The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.

Synthesis of benzothiadiazine-1-oxides by rhodium-catalyzed C-H amidation/cyclization

A rhodium-catalyzed C-H amidation/cyclization sequence provides benzothiadiazine-1-oxides from sulfoximines and 1,4,2-dioxazol-5-ones in good yields. The reaction is characterized by a high functional group tolerance and, in contrast to most previous transformations of this type, is well-suited for S-alkyl-S-arylsubstituted sulfoximines.

METHOD FOR PRODUCING LACTAM COMPOUND, AND LACTAM COMPOUND PRODUCED THEREBY

The present invention relates to a method for producing a lactam compound from dioxazolone in the presence of a catalyst having a particular ligand, and to a lactam compound produced thereby, and can produce a lactam compound with excellent selectivity and an excellent yield by using the combination of a starting material having a particular functional group and a particular catalyst having a particular ligand.