19966-27-9

Upstream product

• 75-44-5 phosgene 
• 540-37-4 p-aminoiodobenzene 
• 22693-31-8 azido(4-iodophenyl)methanone 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 103-71-9 phenyl isocyanate 
• 102-07-8 bis(diphenyl)urea 
• 13262-51-6 1-(4-iodophenyl)-3-phenylthiourea 
• 15845-62-2 1-iodo-4-isocyanatobenzene 
• 201230-82-2 carbon monoxide 
• 622-50-4 4-Acetamido-1-iodobenzene 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 57-13-6 urea 

Relevant academic research and scientific papers

Palladium-catalyzed synthesis of symmetrical urea derivatives by oxidative carbonylation of primary amines in carbon dioxide medium

An efficient palladium-catalyzed synthesis of symmetrically disubstituted ureas via oxidative carbonylation of primary amines is described. The reactions are carried out in the presence of a large excess of carbon dioxide as reaction medium or under solvent-free conditions. The adopted catalyst such as potassium tetraiodopalladate, stable and easy to prepare, allows the use of air as a cheap oxidizing agent. The reactions yield urea and water as the only by-product and proceed with high efficiency with aliphatic and aromatic amines as well. While with primary aliphatic amines, no significant improvement on reactivity is observed when carbon dioxide is used as a solvent, in comparison with the conventional ones, a remarkable high efficiency is obtained with aromatic amines, which shows a dramatic increase in the performance of the catalyst, in terms of turnover number (TON), the highest known so far for this kind of process. Reactions take place in two-phase systems consisting of a homogeneous liquid phase formed by the CO2 expanded amine solution containing the catalyst and a supercritical phase of CO2, CO, O2, and N2.

Hydrogen and halogen bonding in a concerted act of anion recognition: F- induced atmospheric CO2 uptake by an iodophenyl functionalized simple urea receptor

Two simple urea based para-halo substituted [Iodo (L1) and Bromo (L2)] acyclic receptors have been extensively studied as a receptor for various anions. Receptors L1 efficiently uptake atmospheric CO2 and stabilize as air-stable crystals of HCO3- dimer (complex 1a) in the presence of n-tetrabutylammonium (n-TBA) fluoride through the simultaneous formation of hydrogen and halogen bonding, yielding a tetrahedrally surrounded non-covalent coordinated complex. However, receptor L2, in the presence of n-TBA salt of F-, has been found to form a complex with the octahedral SiF62- anion, where the coordination environment of the anion is merely governed by multiple N-H...F (anion) interactions. The fluoride induces an uptake of aerial CO2 only for L1, which is due to the unique ability of L1 to simultaneously form both hydrogen and halogen bonds with an anionic guest. The most decisive evidence supporting the ability of L1 to form a halogen bond is obtained via crystallizing the acetate complex of both the receptors. The receptor L1 stabilizes the acetate anion via both H-bonding and halogen bonding interactions, while the receptor L2 only forms H-bonding interactions with acetate anion. The solution-state anion binding properties of L1 and L2 have been investigated by qualitative and quantitative 1H NMR titration experiments with halides and oxyanions in DMSO-d6. Both the receptors showed strong solution-state binding with F-, HCO3- and CH3COO-, as observed in the solid-state, whereas both of them have been found to be less interactive with other anions such as Cl-, Br-, I-, NO3-, HSO4-, and H2PO4-. This journal is

Method for preparing symmetric urea compound

The invention provides a novel reaction system for synthesizing a symmetric urea compound by taking CO2 as a carbonylation reagent, wherein Lewis base and hydrosilane are used as accelerators and efficiently enable an aromatic/aliphatic primary amine compound to react with normal-pressure CO2 to generate corresponding symmetric urea compounds containing different functional groups under mild conditions (100 DEG C, diglyme). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of toxic carbonylation reagents, isocyanate, high-pressure CO2, expensive dehydrating agents and precious metals is avoided, purification and separation ofintermediates are not needed, pure products can be obtained only through simple suction filtration and separation after the reaction is finished, and the method is an efficient and novel synthesis method and has high industrial application value.

Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3

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.

Effective approach to ureas through organocatalyzed one-pot process

An efficient approach to N, N′-unsymmetrically substituted ureas 9 has been developed through the ammonolysis process of N-Boc protected anilines 7 with amines prompted by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Moreover, a convenient protocol for the

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid

An efficient regioselective iodination of N-phenylureas was developed using iodine/trichloroisocyanuric acid in acetonitrile at room temperature. This protocol proved to be effective on a broad range of substituted N-phenylureas, forming the p-iodinated compounds in 65-96% yield under mild and neutral conditions.

Hydrogen-Bonded Homoleptic Fluoride-Diarylurea Complexes: Structure, Reactivity, and Coordinating Power

Hydrogen bonding with fluoride is a key interaction encountered when analyzing the mode of action of 5′-fluoro-5′-deoxyadenosine synthase, the only known enzyme capable of catalyzing the formation of a C-F bond from F-. Further understanding of the effect of hydrogen bonding on the structure and reactivity of complexed fluoride is therefore important for catalysis and numerous other applications, such as anion supramolecular chemistry. Herein we disclose a detailed study examining the structure of 18 novel urea-fluoride complexes in the solid state, by X-ray and neutron diffraction, and in solution phase and explore the reactivity of these complexes as a fluoride source in SN2 chemistry. Experimental data show that the structure, coordination strength, and reactivity of the urea-fluoride complexes are tunable by modifying substituents on the urea receptor. Hammett analysis of aryl groups on the urea indicates that fluoride binding is dependent on σp and σm parameters with stronger binding being observed for electron-deficient urea ligands. For the first time, defined urea-fluoride complexes are used as fluoride-binding reagents for the nucleophilic substitution of a model alkyl bromide. The reaction is slower in comparison with known alcohol-fluoride complexes, but SN2 is largely favored over E2, at a ratio surpassing all hydrogen-bonded complexes documented in the literature for the model alkyl bromide employed. Increased second-order rate constants at higher dilution support the hypothesis that the reactive species is a 1:1 urea-fluoride complex of type [UF]- (U = urea) resulting from partial dissociation of the parent compound [U2F]-. The dissociation processes can be quantified through a combination of UV and NMR assays, including DOSY and HOESY analyses that illuminate the complexation state and H-bonding in solution.

Catalytic oxidative carbonylation of arylamines to ureas with W(CO) 6/I2 as catalyst

The oxidative carbonylation of aniline to N,N'-diphenylurea was carried out by using W(CO)6 as the catalyst, I2 as the oxidant, CO as the carbonyl source and 4-(dimethylamino)pyridine (DMAP) as base. The reaction conditions were optimized with respect to different bases, molar ratio of DMAP/iodine, temperature, time, and CO pressure. Various p-substituted arylamines can be converted into the respective symmetrical and unsymmetrical N,N'-disubstituted ureas in moderate to good yields. The reaction demonstrated broad tolerance of functionality.

An N,N′-diaryl urea based conjugated polymer model system

An N,N′-diphenyl urea was designed as a model system for aggregation phenomenon in poly(phenyleneethynylenes) (PPEs). The unmethylated N,N′-diphenyl urea adopts an open, unfolded conformation in which the two diphenyl acetylene fluorophores are far enough away, mimicking the unaggregated state. Dimethylation forces the aromatic surfaces together into π-π contact, mimicking the aggregated state of PPEs. Analogous to bulk PPEs, this model system shows dramatic differences in quantum yield between the folded and unfolded states, with the unfolded urea having greater than 400-fold higher fluorescence quantum yield than its folded equivalent.