85630-20-2

Upstream product

• 88-10-8 N,N-diethylcarbamyl chloride 
• 1193-00-6 sodium 4-chlorophenolate 
• 54468-47-2 ethyl-chloro-carbamic acid ethyl ester 
• 106-48-9 4-chloro-phenol 
• 617-84-5 N-formyldiethylamine 
• 1011501-99-7 (4-chlorophenyl)(4-methoxyphenyl)iodonium triflate 
• 124-38-9 carbon dioxide 
• 109-89-7 diethylamine 

Downstream Products

• 98360-95-3 O-2-carboxy-4-chlorophenyl diethylcarbamate 
• 85630-33-7 N,N-diethyl-2-hydroxy-5-chlorobenzamide 
• 98360-96-4 O-(2-N,N-diethylcarbamoyl-4-chloro)phenyl N,N-diethylcarbamate 
• 16281-39-3 5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-(1H)-2-benzopyran-7-carboxylic acid 
• 98361-00-3 N,N-diethyl-2-methoxy-3-(diethylcarbamoyl)-5-chlorobenzamide 
• 98361-02-5 N,N-diethyl-2-methoxy-3-(diethylcarbamoyl)-5-chloro-6-allylbenzamide 
• 1025324-58-6 2-but-2-ynoyl-4-chlorophenyl diethylcarbamate 
• 1245824-50-3 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl N,N-diethylcarbamate 
• 1384974-86-0 C₂₀H₂₄ 
• 182962-33-0 C₁₂H₁₆ClNO₂ 
• 1417448-23-7 (E)-methyl 3-(5-chloro-2-((diethylcarbamoyl)oxy)phenyl)oct-2-enoate 
• 1453186-20-3 (E)-methyl 3-(5-chloro-2-((diethylcarbamoyl)oxy)phenyl)acrylate 

Relevant academic research and scientific papers

The synthesis of phenyl carbamates catalyzed by iron (II) bromide: An oxidative approach for cross-coupling of phenols with formamides

The carbamate group is a key structural motif in many approved drugs and pro-drugs. There is increasing use of carbamates in the medicinal chemistry and agrochemical industry. We present, reagents and chemical methodologies for the synthesis of carbamates, and recent applications. The direct coupling of simple phenols with mono- and di-alkyl formamides provided the phenylcarbamate products.

Experimental and computational study of the 1,5-o → n carbamoyl snieckus-fries-type rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

Directed ortho-Metalation of Aryl Amides, O-Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation

A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt2, in comparison with the OCONEt2 DMG is described. In addition, the

1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement

The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.

Base-Promoted Coupling of Carbon Dioxide, Amines, and Diaryliodonium Salts: A Phosgene- and Metal-Free Route to O-Aryl Carbamates

A phosgene- and metal-free synthesis of O-aryl carbamates is realized through a three-component coupling of carbon dioxide, amines and diaryliodonium salts. The reaction only requires a base as the promoter, providing access to a diverse array of O-aryl c

Ligand-assisted copper-catalyzed oxidative cross-coupling of simple phenols with formamides for the synthesis of carbamates

An oxidative approach for the synthesis of phenyl carbamates has been achieved by ligand-assisted copper-catalyzed cross-dehydrogenative coupling (CDC) of phenols with formamides. The direct coupling of simple phenols with mono- and dialkyl formamides pro

Coumarin derivatives as protease inhibitors and antiviral agents

The present invention relates to novel coumarin derivatives and related compounds which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The coumarin derivatives are useful in the development of therapies for the treatment of viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of multifunctionalized coumarins and of related structures.