Microwave-assisted efficient synthesis of glucose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives catalyzed by sodium acetate.
A novel approach to synthesize glucose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazoles with the assistance of microwave irradiation was developed. The effects of different catalysts on the heterocyclization process were investigated, and the reaction conditions were optimized, with NaOAc emerging as the catalyst of choice. Under the optimized conditions, a series of novel 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives 4 and 5 were successfully synthesized from hydrazones 2 and 3. The absolute configurations of hydrazones 2, 3 and oxadiazoles 4, 5 were confirmed by NMR spectroscopic data. The ratio of the isomers 4 and 5 was approximately 1:1.
Wang
Lin-Na
LN
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
Han
Dong
D
Xu
Fei-Fei
FF
Meng
Xiang-Bao
XB
Li
Zhong-Jun
ZJ
D002384:Catalysis; D005947:Glucose / Q000737:chemistry*; D006358:Hot Temperature; D008872:Microwaves; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D019346:Sodium Acetate / Q000737:chemistry*; D013237:Stereoisomerism
D010080:Oxazoles; D019346:Sodium Acetate; D005947:Glucose