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Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism
Han, Dong2; Meng, Xiang-Bao1,2; Wang, Lin-Na2; Liu, Hong2; Yao, Yun2; Wang, Zhuo1; Yang, Zhen-Jun1; Liu, Zhen-Min1; Li, Zhong-Jun1,2
刊名TETRAHEDRON-ASYMMETRY
2009-03-11
DOI10.1016/j.tetasy.2008.12.033
20期:4页:399-410
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
研究领域[WOS]Chemistry
关键词[WOS]ACETYLATING CONDITIONS ; NMR ANALYSIS ; 1,3,4-OXADIAZOLES ; HETEROCYCLES ; ACID ; BENZOYLHYDRAZONE ; ELUCIDATION
英文摘要

A series of novel alkyl Substituted fructose-based oxadiazoles were synthesized and their cytotoxic activities toward tumor cells were investigated. We studied the reaction mechanism and the stereochemistry of the reaction. Tautomerization between isomers 2 and 3 was observed in solution. The tautomerization was accelerated by heating or in the presence of acetic acid. An intermediate 6 during the heterocyclization was isolated, and two different pathways for the heterocyclization were suggested. On the basis of these findings, an efficient method, with the assistance Of Microwave irradiation was developed for the synthesis of 4 and S. The yields were satisfactory and no by-products were found. We also proposed that the (R/S)-configurations of oxadiazoles were determined by the E/Z configurations of hydrazones. (c) 2009 Elsevier Ltd. All rights reserved,

语种英语
WOS记录号WOS:000265562600002
项目编号20732001 ; 30672525
资助机构National Natural Science Foundation of China
引用统计
被引频次:12[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/62922
专题北京大学药学院_化学生物学系
作者单位1.Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Han, Dong,Meng, Xiang-Bao,Wang, Lin-Na,et al. Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism[J]. TETRAHEDRON-ASYMMETRY,2009,20(4):399-410.
APA Han, Dong.,Meng, Xiang-Bao.,Wang, Lin-Na.,Liu, Hong.,Yao, Yun.,...&Li, Zhong-Jun.(2009).Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism.TETRAHEDRON-ASYMMETRY,20(4),399-410.
MLA Han, Dong,et al."Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism".TETRAHEDRON-ASYMMETRY 20.4(2009):399-410.
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