title: Microwave-assisted efficient synthesis of glucose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives catalyzed by sodium acetate.
abstract: 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.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
authors.forename: Lin-Na
authors.initials: LN
authors.lastname: Wang
authors.forename: Dong
authors.initials: D
authors.lastname: Han
authors.forename: Fei-Fei
authors.initials: FF
authors.lastname: Xu
authors.forename: Xiang-Bao
authors.initials: XB
authors.lastname: Meng
authors.forename: Zhong-Jun
authors.initials: ZJ
authors.lastname: Li
mesh_terms: 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
chemical_list: D010080:Oxazoles; D019346:Sodium Acetate; D005947:Glucose