69805-79-4

Upstream product

• 110-91-8 morpholine 
• 69805-66-9 benzylcarbamic acid 1,1,4-trioxo-2,5-diphenyl-4,5-dihydro-1H-1λ⁶-thiophen-3-yl ester 
• 121820-08-4 Benzyl-carbamic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 
• 6976-49-4 morpholine-4-carboxylic acid ethyl ester 
• 100-46-9 benzylamine 
• 4257-83-4 benzyl 2,2,2-trichloroacetamide 
• 88333-03-3 Benzyl isocyanide 
• 33054-04-5 phenylacetyl azide 
• 103-82-2 phenylacetic acid 
• 1530-89-8 N-cyanomorpholine 
• 100-51-6 benzyl alcohol 
• 93605-74-4 4-[(1H-imidazol-1-yl)carbonyl]morpholine 
• 124-38-9 carbon dioxide 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

N-functionalized benzotriazole-1-carboximidoyl chlorides: Synthetic equivalents for isocyanide dichlorides

Readily prepared N-functionalized benzotriazole-1-carboximidoyl chlorides are proposed as stable and novel isocyanide dichloride synthetic equivalents. Subsequent condensations of these new intermediates afford polysubstituted guanidines, S-aryl isothiour

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.

METHOD OF CONVERTING CARBON DIOXIDE INTO CARBONYL COMPOUNDS

The present invention provides a method for fixing carbon dioxide gas as a carbonyl compound represented by formula (3) as depicted by Figure 1 and comprising, purging of carbon dioxide in a solution of a nucleophile represented by the formula (1) in presence of a solvent at a temperature ranging from -40 Degree Celsius to 35 Degree Celsius, followed by adding a reagent at temperature ranging from -40 degree to 35 degree and thereafter adding another nucleophile represented by the formula (2) to obtain carbonyl compound represented by formula (3). The present invention can be advantageously used to obtain commercially important carbonyl compounds and clean unwanted carbon dioxide gas from the atmosphere and industrial effluents.

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.

Facile direct synthesis of unsymmetrical ureas from N-Alloc-, N-Cbz-, and N-Boc-protected amines using DABAL-Me3

A practical synthetic method for the direct synthesis of unsymmetrically substituted ureas from N-Alloc-, N-Cbz-, and N-Boc-protected amines is described. In this study, efficient direct conversion of the Alloc-, Cbz-, and Boc-carbamate compounds to ureas was achieved in the presence of DABAL-Me3, an air stable and easily handled reagent. Using this reaction method, both protected aromatic and aliphatic amines were successfully transformed into various trisubstituted and tetrasubstituted ureas with high yields without side product. Our findings offer promising guidelines for direct preparation of useful ureas from N-Alloc-, N-Cbz-, and N-Boc-carbamates.

A green, isocyanide-based three-component reaction approach for the synthesis of multisubstituted ureas and thioureas

A one-pot, isocyanide based multicomponent protocol was presented starting from secondary amines towards (thio)urea derivatives and utilized for the construction of a diverse 27-membered chemical library. Following a green compatible microwave assisted condition, the formed N,N′-multisubstituted (thio)ureas were obtained in up to 85% yield.

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.

Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes

Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C-C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.

A Facile and Efficient Method for the Formation of Unsymmetrical Ureas Using DABAL-Me3

A practical synthetic method for the formation of unsymmetrical-substituted ureas is described. The synthesis of the unsymmetrical ureas was readily performed from 2,2,2-trichloroethyl carbamate compounds by treatment of amines with bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane (DABAL-Me3). Using this reaction protocol, various trisubstituted and tetrasubstituted ureas were synthesized in high yields. This study offers a promising approach for the facile synthesis of a variety of unsymmetrical ureas from 2,2,2-trichloroethyl carbamates.

Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines

A novel one-pot synthesis of unsymmetrical ureas, carbamates and thiocarbamates from Cbz-protected amines has been developed. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, isocyanates are generated in situ, which facilitate rapid reaction with amines, alcohols, and thiols to afford the corresponding ureas, carbamates and thiocarbamates in high yields.