کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5223084 | 1383476 | 2010 | 8 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Michael versus retro-Michael reaction in the regioselective synthesis of N-1 and N-3 uracil adducts
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
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چکیده انگلیسی
By controlling the temperature or reaction time in the base-catalysed Michael-type addition of 5-substituted uracil derivatives we were able to synthesise N-1 or N-3 uracil adducts using methyl acrylate and acrylonitrile as acceptors. The mechanism of this chemical inequivalence was established using 1H NMR spectroscopic studies. The investigations revealed that formation of the N-1 adduct was achievable under kinetically controlled conditions irrespective to the type of the base used (TEA, DBU). In turn, synthesis of the N-3 adducts proceeded from the initially formed N-1,N-3 diadduct via a retro-Michael reaction which dominates at elevated temperature or prolonged reaction time.
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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 66, Issue 43, 23 October 2010, Pages 8450–8457
Journal: Tetrahedron - Volume 66, Issue 43, 23 October 2010, Pages 8450–8457