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 |
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Authors: | Dong Han Xiang-Bao Meng Lin-Na Wang Hong Liu Yun Yao Zhuo Wang Zhen-Jun Yang Zhen-Min Liu Zhong-Jun Li |
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Institution: | 1. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, People’s Republic of China;2. Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, People’s Republic of China |
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Abstract: | 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 5. 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. |
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