95766-89-5

Upstream product

• 110-91-8 morpholine 
• 201230-82-2 carbon monoxide 
• 104-94-9 4-methoxy-aniline 
• 15159-40-7 4-morpholinocarbonyl chloride 
• 10349-38-9 p-methoxyphenylisonitrile 
• 124-38-9 carbon dioxide 
• 4257-81-2 2,2,2-trichloro-N-(4-methoxyphenyl)acetamide 
• 126680-08-8 (E,Z)-3-(4-methoxyphenyl)-5-phenylmethylene-2,4-dioxothiazolidine 
• 5416-93-3 4-Methoxyphenyl isocyanate 
• 10507-69-4 4-methoxybenzohydroxamic acid 

Relevant academic research and scientific papers

Cesium Carbonate-Promoted P-Alkylation of Phosphinecarboxamides

An effective method for the P-alkylation of N -arylphosphinecarboxamides was demonstrated. Primary N -arylphosphinecarboxamides without additional protection underwent P-monoalkylation with various alkyl halides in the presence of cesium carbonate as a promoter. The reactivity of phosphinecarboxamides was also explored.

Chemoselective isocyanide insertion into the N-H bond using iodine-DMSO: Metal-free access to substituted ureas

Insertion of isocyanides into the N-H bond gives access to many medicinally important and structurally diverse complex nitrogen-containing heterocycles. Although the transition metal catalyzed isocyanide insertion into the N-H bond is very common, polymerization of isocyanides in the presence of a transition metal and their strong coordination with metals are the common drawbacks. On the other hand, the inertness of most of the isocyanides towards amines in the absence of a metal catalyst has stymied the growth of the metal-free approach for isocyanide insertion into amines. As a result, only a handful of metal catalysed methods with limited substrate scopes have been reported for the synthesis of ureas via isocyanide insertion into amines and no metal-free version has been reported yet. Interestingly, chemoselective isocyanide insertion into amines has not been reported in the literature. We employed the I2-DMSO reagent system for the chemoselective synthesis of ureas, where isocyanides react with aliphatic amines only, while aromatic amines need a nucleophilic activator (DABCO) to facilitate the formation of ureas. This method gave direct and chemoselective access to ureas by evading the commonly used yet toxic isocyanates.

Metal-Free Synthesis of Unsymmetrical Ureas and Carbamates from CO2 and Amines via Isocyanate Intermediates

A mild and metal-free synthesis of aryl isocyanates from arylamines under an atmosphere of CO2 was developed. The carbamic acid intermediate, derived from the arylamine starting material and CO2 in the presence of DBU, is dehydrated by activated sulfonium reagents to generate the corresponding isocyanate. The latter can be detected by in situ IR and trapped by various amines and alcohols to make unsymmetrical ureas and carbamates, respectively. Dicarbamates can also be prepared in good yields via the mild dehydration of the corresponding dicarbamic acids.

Rhodium(iii)-catalysed aerobic synthesis of highly functionalized indoles from N-arylurea under mild conditions through C-H activation

A Rh(iii) catalysed amino arylation of alkynes using copper as the terminal oxidant for regeneration of the catalytically active species under aerobic conditions is described. This novel C-H activation reaction was applied to the synthesis of a wide range of substituted indoles from N-arylureas.

Bromodimethylsulfonium bromide (BDMS)-mediated Lossen rearrangement: Synthesis of unsymmetrical ureas

Bromodimethylsulfonium bromide (BDMS) was found to be a very efficient reagent for Lossen rearrangement of hydroxamic acids to the corresponding isocyanates which were subsequently trapped in situ with various amines to afford unsymmetrical ureas in good to excellent yields (64-89%). The protocol is experimentally simple, mild, and represents valuable alternative to the existing methods for in situ activation of hydroxamic acids promoting Lossen rearrangement.

Synthesis of some N-alkyl substituted urea derivatives as antibacterial and antifungal agents

A series of N-alkyl substituted urea derivatives were synthesized and evaluated for their in vitro antibacterial and antifungal activities. The N-alkyl substituted urea derivatives bearing morpholine moiety (3a-3k) showed better activities than those bearing diethylamine moiety (2a-2f). Compounds having fluoro substituent at ortho (3c) and para (3b) positions of the phenyl ring exhibited potent antimicrobial activities against Gram-positive and Gram-negative bacteria as well as fungi.

Efficient synthesis of ureas by direct palladium-catalyzed oxidative carbonylation of amines

A general synthesis of symmetrically disubstituted ureas and trisubstituted ureas by direct Pd-catalyzed oxidative carbonylation of primary amines or of a mixture of a primary and a secondary amine, respectively, with unprecedented catalytic efficiencies for this kind of process, is reported. Reactions are carried out at 90-100 °C in DME as the solvent in the presence of PdI 2 in conjunction with an excess of KI as the catalytic system and under 20 atm of a 4:1 mixture of CO and air. In some cases, working in the presence of an excess of CO2 (40 atm) in addition to CO and air (60 atm total) had a beneficial effect on substrate reactivity and product yield. Cyclic five-membered and six-membered ureas were easily formed from primary diamines. The methodology has been successfully applied to the synthesis of pharmacologically active ureas, such as those deriving from α-amino esters or urea NPY5RA-972, a potent antagonist of the neuropeptide Y5 receptor.

A novel synthesis of isocyanates and ureas via β-elimination of haloform

A novel synthesis of isocyanates via base-induced β-elimination of haloform from N-monosubstituted trihaloacetamides is described. The rate of reaction exhibits a strong dependence on the nature of the trihalomethyl group. Thus, while the reaction of tribromoacetamides proceeds at room temperature and the reaction of trichloroacetamides requires heating in polar solvents, no reaction could be observed for any of the corresponding trifluoro derivatives. This novel β-elimination of haloform from stable and readily available trihaloacetamides was applied to a 'one-pot' synthesis of ureas which avoids the use of phosgene and isolation of isocyanates.

Studies on 4-Thiazolidinones. VIII, The Role of Substituents at Position-3 on the Mode of Cleavage of 5-Arylmethylene-2,4-dioxothiazolidines

Hydrazine hydrate, morpholine and benzylamine react with 3-aryl-5-arylmethylene-2,4-dioxothiazolidines 1a-d to give mixtures of thiolopropenamides 2, ethylideneamino-biuret 3 and/or 4-arylamidocarboxamides 4 in varying proportions.However, 3-benzyl-5-aryl