1932-38-3

Upstream product

• 110-78-1 Propyl isocyanate 
• 62-53-3 aniline 
• 54680-33-0 propyl-carbamoyl azide 
• 876495-49-7 N-nitro-N'-propyl-urea 
• 141-75-3 butyryl chloride 
• 107-10-8 propylamine 
• 23583-11-1 aminophenyl-N-hydroxysuccinimidyl carbamate 
• 6320-72-5 4-nitrophenyl-N-phenyl carbamate 
• 107-92-6 butyric acid 
• 103-71-9 phenyl isocyanate 
• 96-49-1 [1,3]-dioxolan-2-one 
• 372-09-8 cyanoacetic acid 
• 582-61-6 benzoyl azide 
• 201230-82-2 carbon monoxide 

Downstream Products

• 301206-14-4 1-(2-Cyano-acetyl)-3-phenyl-1-propyl-urea 
• 91467-19-5 1-phenyl-3-propyl-2,4,5-imidazolidinetrione 
• 117740-74-6 6-amino-5-nitroso-1-phenyl-3-n-propyl-2.4-(1H, 3H)-pyrimidinedione 
• 117740-75-7 5,6-diamino-1-phenyl-3-n-propyl-2,4-(1H, 3H)-pyrimidinedione 
• 176370-51-7 6-amino-1-phenyl-3-propylpyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Synthesis method of substituted urea compound

The invention discloses a synthesis method of a substituted urea compound, which comprises the following steps: stirring aldehyde, N-aryl urea, trichlorosilane and Lewis base in an organic solvent ata temperature range of -20 DEG C to room temperature for

Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement

Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.

A Fe3O4?SiO2/Schiff Base/Pd Complex as an Efficient Heterogeneous and Recyclable Nanocatalyst for One-Pot Domino Synthesis of Carbamates and Unsymmetrical Ureas

A palladium-catalyzed domino method for the direct synthesis of carbamates and ureas has been developed by using readily available and economical starting materials (aryl halide, carbon monoxide, sodium azide, amines and alcohols) in a one-pot approach. The domino process underwent carbonylation, Curtius rearrangement, and nucleophilic addition. This protocol provides a step-economical and highly efficient reaction to access the wide range of valuable carbamates, symmetrical and unsymmetrical ureas with high yields under remarkable mild reaction conditions that are important factors in pharmaceutical science, biochemistry and agricultural industries. Furthermore, the magnetically recoverable nanocatalyst (Fe3O4?SiO2/Pd(II)) can be conveniently and swiftly recycled using external magnet and reused at least for seven times without noticeable loss of its catalytic activity.

Synthesis and architecture of polystyrene-supported Schiff base-palladium complex: Catalytic features and functions in diaryl urea preparation in conjunction with Suzuki-Miyaura cross-coupling reaction by reductive carbonylation

This work represents an efficient and unique phosphine-free approach for the polystyrene embedded Schiff-base palladium catalyzed diaryl urea synthesis and Suzuki-Miyaura cross-coupling reaction by reductive carbonylation process. The careful instrumental investigations with FE-SEM, TEM, EDAX, TGA, UV–Vis, FTIR, AAS, and elemental analysis precisely characterized the developed heterogeneous catalyst. Reaction parameters, like catalytic natures, starting materials, reaction environment, and solvent were examined sequentially. The present work has been adequately addressed to account for the generation and characterization of a new polymer bound Pd-catalyst and using it in the synthesis of diaryl ureas and diaryl ketones, with no substantial decay of catalytic activity.

2-Oxo-1,2-dihydropyridinyl-3-yl amide-based GPa inhibitors: Design, synthesis and structure-activity relationship study

Glycogen phosphorylase (GP), which plays a crucial role in the conversion of glycogen to glucose-1-phosphate, is a target for therapeutic intervention in diabetes. In this study, we report the design and synthesis of 29 new derivatives of 2-oxo-1,2-dihydro pyridin-3-yl amides, as potential inhibitors of GP. The hit rate (45%) was high with 13 compounds inhibiting GPa (between 33% at 4.40 mM and an IC50 of 1.92 μM). Two lead compounds were identified as compounds exhibiting good GPa inhibition (IC50 = 2.1 and 1.92 μM). SAR analysis of these compounds revealed sensitivity of GPa to the length of the 2-oxo-1,2-dihydro pyridin-3-yl amide derivative and a preference for inclusion of a 3,4-dichlorobenzyl moiety.

Reduced reactivity of amines against nucleophilic substitution via reversible reaction with carbon dioxide

The reversible reaction of carbon dioxide (CO2) with primary amines to form alkyl-ammonium carbamates is demonstrated in this work to reduce amine reactivity against nucleophilic substitution reactions with benzophenone and phenyl isocyanate. The reversible formation of carbamates has been recently exploited for a number of unique applications including the formation of reversible ionic liquids and surfactants. For these applications, reduced reactivity of the carbamate is imperative, particularly for applications in reactions and separations. In this work, carbamate formation resulted in a 67% reduction in yield for urea synthesis and 55% reduction for imine synthesis. Furthermore, the amine reactivity can be recovered upon reversal of the carbamate reaction, demonstrating reversibility. The strong nucleophilic properties of amines often require protection/de-protection schemes during bi-functional coupling reactions. This typically requires three separate reaction steps to achieve a single transformation, which is the motivation behind Green Chemistry Principle #8: Reduce Derivatives. Based upon the reduced reactivity, there is potential to employ the reversible carbamate reaction as an alternative method for amine protection in the presence of competing reactions. For the context of this work, CO2 is envisioned as a green protecting agent to suppress formation of n-phenyl benzophenoneimine and various n-phenyl-n-alky ureas.

Synthesis of N-1′, N-3′-disubstituted spirohydantoins and their anticonvulsant activities in pilocarpine model of temporal lobe epilepsy

Herein we report the synthesis and anticonvulsant activity of a library of eighteen new compounds that are structural mimics of phenytoin. These class of compounds contain a N-1′, N-3′-disubstituted spirohydantoin scaffold, where the N-1′ and N-3′ positions are modified with an alkyl group or aryl group. Of the eighteen compounds synthesized and tested, compound 5c showed the best anticonvulsant activity. It completely prevented the precursor events of motor seizure in the pilocarpine model of temporal lobe epilepsy. Additionally, ten of the analogs were more effective than phenytoin when compared using the Racine's score in the pilocarpine model. Based on the structure activity relationship (SAR), we concluded that alkyl groups (ethyl, propyl or cyclopropyl) at N-3′ position and 4-nitro phenyl group at N-1′ position are desirable.

Low molecular weight MPEG-assisted organic synthesis

A toolkit of low molecular weight MPEG-supported coupling agents ( MIIDQ, MEDCI), reagents for the Mitsunobu reaction ( MDEAD, MTPP), an alternative to diazomethane, and scavengers can be used in the solution-phase synthesis of amides, esters and ureas and are easily removed after use by solid-phase extraction (MSPE) using normal silica.

The preparation and characterization of nineteen new phthalidyl spirohydantoins

Abstract - Nineteen new N,N-disubstituted phthalidyl spirohydantoins (6a-s) were prepared for the purpose of pharmacological testing. Their structure was deduced from the IR, 1H-NMR, 13C-NMR, mass spectra and elemental analysis. The two possible structural isomers - only one of which is formed - can be distinguished unequivocally on the basis of selective diastereotopicity of the α-methylene hydrogens adjacent to N-3′ of the hydantoin ring.

One-pot synthesis of [11C]ureas via triphenylphosphinimines

A series of 11C-labeled ureas was prepared using a rapid and efficient one-pot procedure. First, the intermediate [11C] phenylisocyanate was formed with phenyltriphenylphosphinimine and [ 11C]CO2. A range of amines was then reacted with the [11C]phenylisocyanate yielding the [11C]urea derivatives in short synthesis times. This easy-to-handle method circumvents disadvantages of known procedures and generates the possibility to prepare other kinds of 11C-labeled compounds using a variety of phenylphosphinimines in combination with different nucleophiles. The presented approach is an alternative to the use of established methods in 11C-labeling chemistry. Copyright