Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts
نویسندگان
چکیده
منابع مشابه
Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts**
Since the 1864 landmark discovery by Adolf von Baeyer, barbituric acids have played a prominent role in medicine and organic synthesis. The barbituric acid scaffold occurs in more than 5000 pharmacologically active compounds, including commonly used anticonvulsant, hypnotic, and anticancer agents (Figure 1a). Moreover, as an easily accessible feedstock material, it is an extremely useful buildi...
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15 صفحه اولStructural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to a-hydroxy-N-acyl-carbamides†
Structural characterisation and reactivity of new tetrahedral intermediates based on a highly modular barbituric acid scaffold, formed via chemoselective electron transfer using the SmI2–H2O reagent, are reported. Lewis acid promoted cleavage of bicyclic a-amino alcohols affords vinylogous N-acyliminium ions, which undergo selective (>95 :5, 1,4 over 1,2) capture with a suite of diverse nucleop...
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Structural characterisation and reactivity of new tetrahedral intermediates based on a highly modular barbituric acid scaffold, formed via chemoselective electron transfer using the SmI2-H2O reagent, are reported. Lewis acid promoted cleavage of bicyclic α-amino alcohols affords vinylogous N-acyliminium ions, which undergo selective (>95 : 5, 1,4 over 1,2) capture with a suite of diverse nucleo...
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ژورنال
عنوان ژورنال: Angewandte Chemie
سال: 2013
ISSN: 0044-8249
DOI: 10.1002/ange.201306484