14040-79-0

Upstream product

• 144-62-7 oxalic acid 
• 64-04-0 phenethylamine 
• 95-92-1 oxalic acid diethyl ester 
• 3659-97-0 1-methylparabanic acid 
• 49837-58-3 2-methoxy-5-morpholino-1,3-oxazole-4-carbonitrile 
• 79-37-8 oxalyl dichloride 
• 107-21-1 ethylene glycol 
• 78-83-1 2-methyl-propan-1-ol 
• 81682-58-8 Oxalic acid N-(2-phenylethyl)monoamide 
• 20172-98-9 N-Phenethyl-oxalamic acid methyl ester 

Downstream Products

• 64-04-0 phenethylamine 
• 84500-68-5 1,1'-bi(1,2,3,4-dihydroisoquinolyl) 

Relevant academic research and scientific papers

Novel chiral C1-1′,2′,3′,4′-tetrahydro-1,1′- bisisoquinolines: synthesis, resolution, and applications in catalytic enantioselective reactions

A straightforward synthesis of a structurally constrained C1-1′,2′,3′,4′-tetrahydro-1,1′- bisisoquinoline 1 is described. Resolution of this compound has been achieved successfully. The preparation of chiral N-alkyl, urea, and thiourea derivati

Recyclization of 2-methoxy-5-morpholino-1,3-oxazole-4-carbonitrile by benzylamine, phenethylamine, and phenylhydrazine

Reaction of 2-methoxy-5-morpholino-1,3-oxazole-4-carbonitrile with benzylamine, phenethylamine and phenylhydrazine results in the new substituted 5-amino-2,3-dihydro-1H-imidazol-2-ones.

Urethanes synthesis from oxamic acids under electrochemical conditions

Urethane synthesis via oxidative decarboxylation of oxamic acids under mild electrochemical conditions is reported. This simple phosgene-free route to urethanes involves an in situ generation of isocyanates by anodic oxidation of oxamic acids in an alcoholic medium. The reaction is applicable to a wide range of oxamic acids, including chiral ones, and alcohols furnishing the desired urethanes in a one-pot process without the use of a chemical oxidant.

Synthesis of oxalamides by acceptorless dehydrogenative coupling of ethylene glycol and amines and the reverse hydrogenation catalyzed by ruthenium

A sustainable, new synthesis of oxalamides, by acceptorless dehydrogenative coupling of ethylene glycol with amines, generating H2, homogeneously catalyzed by a ruthenium pincer complex, is presented. The reverse hydrogenation reaction is also accomplished using the same catalyst. A plausible reaction mechanism is proposed based on stoichiometric reactions, NMR studies, X-ray crystallography as well as observation of plausible intermediates.

Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction

A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.

Cu/ N, N′-Dibenzyloxalamide-Catalyzed N-Arylation of Heteroanilines

N,N′-Dibenzyloxalamide (DBO) was identified as a powerful ligand for promoting Cu-catalyzed coupling of heteroanilines with (hetero)aryl halides. For (hetero)aryl chlorides, the coupling reaction occurred at 130 °C with 5 mol % CuBr and 10 mol % DBO. For

Total synthesis of a marine imidazole alkaloid, clathridine A

The first total synthesis of clathridine A (8), a marine imidazole alkaloid, was achieved by using a novel regioselective condensation as a key step, in which preclathridine A (2) was treated with 1-methylparabanic acid (11) in the presence of a silylating agent. (C) 2000 Elsevier Science Ltd.

Three-center intramolecular hydrogen bonding in oxamide derivatives. NMR and X-ray diffraction study

This contribution describes the synthesis and structural investigation of the symmetric and non-symmetric oxamides N,N′-bis(2-hydroxyphenyl)oxamide 1, N,N′-bis(5-tert-butyl-2-hydroxyphenyl)-oxamide 2, N,N′-bis(3,5-dimethyl-2-hydroxyphenyl)oxamide 3, N,N′-bis(2-hydroxybenzyl)oxamide 4, N,N′-diphenethyloxamide 5, N-(2-hydroxyphenyl)-N′-(2-methoxyphenyl)oxamide 6, N-(2-hydroxy-phenyl)-N′-phenethyloxamide 7, (1S,2R)-(-)-N-(2-hydroxyphenylcarbamoylcarbonyl)norephedrine 8, (1R,2S)-(-)-N-(2-hydroxyphenylcarbamoylcarbonyl) 9, ethyl N-(2-hydroxyphenyl)oxalamate 10 and ethyl N-(2-methoxyphenyl)oxalamate 11. The structures were established by 1H, 13C, 15N and variable temperature NMR spectroscopy. Compounds 1-4 and 6-11 are stabilized by intramolecular three-center hydrogen bonding between the amide proton and two oxygen atoms. The 1H NMR Δδ/ΔT value of the amide proton correlates with the 15N NMR chemical shift. The X-ray diffraction molecular structures of 1 and 11 showed a planar conformation with trans configuration in the solid state, corresponding to the preferred conformation found in solution.

Reactivity of Carbamoyl Radicals. A New, General, Convenient Free-Radical Synthesis of Isocyanates from Monoamides of Oxalic Acid

A new, general, simple synthesis of isocyanates was developed by oxidation of monoamides of oxalix acid with peroxydisulfate catalyzed by Ag and Cu salts.The reaction was carried out in a two-phase system (water and an organic solvent), and it is suitable also for practical applications, due to the simple experimental conditions and the inexpensive as well as nontoxic reagents.The first example of homolytic intramolecular aromatic carbamoylation is also reported.