39200-98-1Relevant academic research and scientific papers
N,N′-Disubstituted Barbituric Acid: A Versatile and Modular Multifunctional Platform for Obtaining β-C-Glycoconjugates from Unprotected Carbohydrates in Water
Portier, Fran?ois,Solier, Justine,Halila, Sami
, p. 6158 - 6162 (2019)
Direct access to non-hydrolyzable glycoconjugates is highly mandatory for stabilizing their intrinsic biological or physical-chemistry properties in the surrounding environment. Here, a simple and versatile approach for the preparation of multifunctional clickable β-C-glycoconjugates has been developed. Readily accessible N,N′-disubstituted barbituric acids have been synthesized and ligated in water to the reducing end of unprotected carbohydrates via Knoevenagel condensation. Additionally, divalent glycoclusters have been built from bis-urea backbones and showed ability to interact with a model lectin, the peanut agglutinin. This concept can be readily adapted for the preparation of other C-glycoconjugates applicable in diverse area of glycosciences.
Unusual behavior nitrogen-containing compounds in the synthesis of O-silylurethanes and trimethylsilylureas
Belova,Pletneva,Shamina,Golub,Korlyukov,Kirilin
, (2014)
The behavior of organic and organosilicon nitrogen - containing compounds-hydrazine, aminopyridine, 2-furylamine, and diazole derivatives - in the synthesis of O-silylurethanes, semicarbazides, and ureas was studied. The structure of the synthesized N,N′-
Method for photocatalytic synthesis of substituted urea compound
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Paragraph 0049-0050; 0057, (2021/06/09)
The invention relates to the technical field of organic synthesis, in particular to a method for photocatalytic synthesis of a substituted urea compound. The method specifically comprises the following steps: mixing tetrahalomethane and a solvent, then adding an amine compound and a catalyst in sequence, stirring and reacting under an oxygen-containing atmosphere and an illumination condition, and then separating and purifying to obtain the substituted urea compound, according to the synthesis method, the raw materials are wide in source, by-products produced after the reaction are halogen simple substances and high in additional value, on one hand, phosgene, triphosgene and the like which are high in toxicity are prevented from being adopted as raw materials, on the other hand, generation of a large amount of waste is avoided, the catalyst can be recycled, the influence of the preparation process on the environment is reduced, and the atom utilization rate of the reaction is improved.
Simple preparation method of N-acyl compound
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Paragraph 0043-0045, (2019/07/04)
The invention relates to a simple preparation method of an N-acyl compound. The simple preparation method comprises the specific steps that an amine compound and R-OCF3 are mixed in a solvent and react for 1 min-48 h at -80-100 DEG C, after the reaction is completed, water is added for quenching, and column separation and purification or recrystallization and purification are carried out to obtainthe N-acyl compound. According to the simple preparation method of the N-acyl compound, the characteristic that a substance containing trifluorooxygen groups can be decomposed in situ to produce fluorophosgene is utilized, and the substance directly reacts with the amine compound to achieve rapid N-carbonylation of an amines substrate and efficiently prepare a urea derivative and a carbamyl fluoride compound. The simple preparation method of the N-acyl compound has the advantages that the operation is simple, the reaction time is short, the application range of the substrate is wide, no catalysts or additives need to be used, the raw materials are easy to obtain, the product yield is high, the purification is easy, and the required compound can be obtained by using a column chromatographyisolation method or recrystallization.
Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
supporting information, p. 10907 - 10912 (2019/08/02)
Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
Iron-catalyzed reaction of urea with alcohols and amines: A safe alternative for the synthesis of primary carbamates
Pe?a-López, Miguel,Neumann, Helfried,Beller, Matthias
, p. 2233 - 2238 (2017/07/25)
A general study of the iron-catalyzed reaction of urea with nucleophiles is here presented. The carbamoylation of alcohols allows for the synthesis of N-unsubstituted (primary) carbamates, including present drugs (Felbamate and Meprobamat, without the necessity to apply phosgene and related derivatives. Using amines as nucleophiles gave rise to the respective mono-and disubstituted ureas via selective transamidation reaction. These atom-economical transformations provide a direct and selective access to valuable compounds from cheap and readily available urea using a simple Lewis-acidic iron(Icatalyst.
Polynuclear Gold [AuI]4, [AuI]8, and Bimetallic [AuI4AgI] Complexes: C?H Functionalization of Carbonyl Compounds and Homogeneous Carbonylation of Amines
Smirnova, Ekaterina S.,Mu?oz Molina, José M.,Johnson, Alice,Bandeira, Nuno A. G.,Bo, Carles,Echavarren, Antonio M.
supporting information, p. 7487 - 7491 (2016/07/06)
The synthesis of tetranuclear gold complexes, a structurally unprecedented octanuclear complex with a planar [AuI8] core, and pentanuclear [AuI4MI] (M=Cu, Ag) complexes is presented. The linear [AuI4] complex undergoes C?H functionalization of carbonyl compounds under mild reaction conditions. In addition, [AuI4AgI] catalyzes the carbonylation of primary amines to form ureas under homogeneous conditions with efficiencies higher than those achieved by gold nanoparticles.
