60718-51-6

Upstream product

• 288-88-0 1,2,4-Triazole 
• 98-88-4 benzoyl chloride 
• 96017-71-9 1,1'-oxalyldi(1,2,4-triazole) 
• 65-85-0 benzoic acid 
• 175351-39-0 1-cyano-1,2,4-triazole 
• 455-32-3 benzoyl fluoride 
• 114825-46-6 [1,2,4]Triazol-1-yl-phosphonic acid 2-chloro-phenyl ester (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(9-phenyl-9H-xanthen-9-yloxymethyl)-tetrahydro-furan-3-yl ester 

Downstream Products

• 201279-57-4 (S)-benzoic acid 1-furan-2-yl-ethyl ester 
• 201279-54-1 (R)-(+)-2-(1-benzoyloxyethyl)furan 
• 93-98-1 N-phenyl benzoyl amide 
• 57473-79-7 benzoic acid (S)-1-phenylethyl ester 
• 13358-49-1 (R)-(1-phenyl)-1-ethyl benzoate 
• 939-48-0 isopropyl benzoate 
• 93-89-0 benzoic acid ethyl ester 
• 288-88-0 1,2,4-Triazole 

Relevant academic research and scientific papers

Esterification with aromatic acyl-1,2,4-triazole Catalyzed by weak base at the rate comparable to acyl chloride

Benzoyl-1,2,4-triazole underwent esterification with a primary alcohol in the presence of 4-(N,N-dimethylamino)pyridine (DMAP) catalyst at the rate comparable to benzoyl chloride. The kinetic study concluded that the reaction proceeds in a similar mechanism to carboxylic acid anhydride and is thus sensitive to the steric hindrance of alcohol. As the esterification of benzoyl-1,2,4-triazole did not afford acidic by-product and require an equimolar or more amount of base, it is effective for the protection of acid-sensitive alcohol and polyester synthesis.

Elucidation of the E-Amide Preference of N-Acyl Azoles

The conformational properties of N-acyl azoles (imidazole, pyrazole, and triazole) were examined. The N-2′,4′,6′-trichlorobenzoyl azoles were stable in methanol at room temperature, and no hydrolyzed products were observed over 7 days in the presence of 5% trifluoroacetic acid or 5% triethylamine in CDCl3. The high stability may be explained by the double-bond amide character caused by the steric hindrance due to the ortho-substituents in the benzoyl group. While specific E-amide preferences were observed in N-acyl pyrazoles/triazoles, the amides of the imidazoles gave a mixture of E and Z. One of the conceivable ideas to rationalize this conformational preference may be repulsive interaction between two sets of lone-pair electrons on the pyrazole 2-nitrogen (nN) and the carbonyl oxygen atoms (nO) in the Z-conformation of N-acyl pyrazoles/triazoles. However, analysis of orbital interactions suggested that in the case of the E-conformation of N-acyl pyrazoles, such electron repulsion is small because of distance. The interbond energy calculations suggested that the Z-conformer is involved in strong vicinal σ-σ repulsion along the amide linkage between the σN1N2 and σC1C2 orbitals in the anti-periplanar arrangement and between the σN1C5 and σC1C2 orbitals in the syn-periplanar arrangement, which lead to the overwhelming E-preference in N-acyl pyrazoles/triazoles. In the case of N-acyl imidazoles, similar vicinal σ-σ repulsions were counterbalanced, leading to a weak preference for the E-conformer over the Z-conformer. The chemically stable and E-preferring N-acyl azoles may be utilized as scaffolds in future drug design.

N-Cyanazoles in Synthesis of Amides of Carboxylic Acids

The reaction of carboxylic acids with 1-cyanimidazole, 1-cyanobenzimidazole, and 1-cyano-1,2,4-triazole leads to the formation of 1-acylazoles used in situ in synthesis of anilides of the corresponding carboxylic acids.

Facile Conversions of Carboxylic Acids into Amides, Esters, and Thioesters Using 1,1'-Oxalyldiimidazole and 1,1'-Oxalyldi(1,2,4-triazole)

Aliphatic, aromatic, and heteroaromatic carboxylic acids react with 1,1'-oxalyldiimidazole (1) or 1,1'-oxalyldi(1,2,4-triazole) (2) in acetonitrile for 40 min at 40 degC to give the corresponding 1-acylazole intermediates (11), which promptly undergo aminolysis and alcoholysis to form amides (13) including dipeptides (14), esters (16), and thioesters (19).These findings show that both 1 and 2 can be utilized as condensing reagents for the synthesis of carboxylic acid derivatives.Keywords --- 1,1'-oxalyldiimidazole; 1,1'-oxalyldi(1,2,4-triazole); 1,1'-carbonyldiimidazole; 1-acylazole; condensing reagent; amidation; esterification; dipeptide; aminolysis; alcoholysis

A NEW SYNTHESIS OF PHOSPHOROFLUORIDATES OF BIOLOGICAL INTEREST. THE REACTION OF PHOSPHOROAZOLIDES WITH BENZOYL FLUORIDE

Phosphoroazolides, including nucleoside derivatives, can be converted smoothly into the corresponding phosphorofluoridates by reaction with benzoyl fluoride.From these compounds oligonucleotides containing P-F instead of P-OH can be prepared.