کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1347244 | 980302 | 2009 | 12 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
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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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی معدنی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
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.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 20, Issue 4, 11 March 2009, Pages 399-410
Journal: Tetrahedron: Asymmetry - Volume 20, Issue 4, 11 March 2009, Pages 399-410
نویسندگان
Dong Han, Xiang-Bao Meng, Lin-Na Wang, Hong Liu, Yun Yao, Zhuo Wang, Zhen-Jun Yang, Zhen-Min Liu, Zhong-Jun Li,