80628-80-4

Upstream product

• 141-97-9 ethyl acetoacetate 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 16673-80-6 6-methyl-2-phenyl-4H-1,3-oxazin-4-one 
• 81467-48-3 O-acetoacetylbenzamide oxime 
• 613-92-3 N-hydroxyl-benzamidine 
• 100-47-0 benzonitrile 
• 613-92-3 (E)-N'-hydroxybenzimidamide 
• 1694-31-1 tert-butyl acetoacetate 
• 81467-48-3 C₁₁H₁₂N₂O₃ 
• 66347-71-5 1-(3-phenyl-[1,2,4]oxadiazol-5-yl)-propan-2-one oxime 

Downstream Products

• 1272665-27-6 5-(4-methyl-6-propyl-2-pyrimidinol-5-yl)-3-phenyl-1,2,4-oxadiazole 
• 1171077-80-7 C₁₉H₁₅ClN₄O₂ 
• 1272665-29-8 5-(4-methyl-6-(3-nitrophenyl)-2-pyrimidinol-5-yl)-3-phenyl-1,2,4-oxadiazole 
• 1272665-28-7 5-(4-methyl-6-phenyl-2-pyrimidinol-5-yl)-3-phenyl-1,2,4-oxadiazole 
• 1170057-86-9 5-(6-methyl-4-phenyl-3,4-dihydro-2(1H)-pyrimidinon-5-yl)-3-phenyl-1,2,4-oxadiazole 
• 1272665-30-1 5-(6-(4-methoxyphenyl)-4-methyl-2-pyrimidinol-5-yl)-3-phenyl-1,2,4-oxadiazole 
• 1172815-15-4 5-(4-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2(1H)-pyrimidinon-5-yl)-3-phenyl-1,2,4-oxadiazole 

Relevant academic research and scientific papers

A one-pot synthesis of 3-substituted-5-carbonylmethyl-1,2,4-oxadiazoles from β-keto esters and amidoximes under solvent-free conditions

Herein we report a high yielding one-pot 'green' synthesis of 3-substituted-5-carbonylmethyl-1,2,4-oxadiazoles from readily available β-keto esters and amidoximes under simple and convenient solvent-free conditions. No additional base is needed. The reaction likely goes through an acyl ketene intermediate.

Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst

Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient catalyst for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles. Using 0.1 - 1.0 equivalents of TBAF in THF for 1 - 24 h at room temperature, alkanoyl- and aroyloxyamidines were converted in high yield to the corresponding 3,5-disubstituted-1,2,4-oxadiazoles. A variety of R and R′ substituents were investigated.

Cyclization of O-Acetoacetylbenzamide Oxime Derivatives

O-Acetoacetylbenzamide oxime derivatives (2) were prepared from benzamide oxime derivatives (1) and diketene at low temperature in almost quantitative yields.Cyclization of 2 in the presence of a strong base proceeded with elimination of acetone to afford 3-aryl-1,2,4-oxadiazolin-5-one derivatives (4) in 77-95percent yields.However, in the cases of the o-, m-, and p-nitrobenzamide oxime derivatives (2f-h), the reaction proceeded with dehydration even in the presence of a strong base to afford 5-acetonyl-3-aryl-1,2,4-oxadiazole derivatives (3f-h) in moderate yields.Possible mechanisms of these cyclization are discussed.