Synthesis of Amino Acid Derived Enaminones via Wolff Rearrangement Using Vinylogous Amides as Carbon Nucleophiles
نویسندگان
چکیده
منابع مشابه
Catalytic synthesis of amides via aldoximes rearrangement.
Amide bond formation reactions are among the most important transformations in organic chemistry because of the widespread occurrence of amides in pharmaceuticals, natural products and biologically active compounds. The Beckmann rearrangement is a well-known method to generate secondary amides from ketoximes. However, under the acidic conditions commonly employed, aldoximes RHC=NOH rarely rearr...
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Mesoporous MCM-41 silicas anchored with sulfonic acid (–SO3H) groups (denoted MSN-SA) via postsynthesis modification are very effective for the Beckman rearrangement. A simple and convenient procedure for conversion of a variety oximes to their corresponding amides and lactams has been developed. The reaction was carried out in the presence of MSN-SA as the catalyst. The best results for conver...
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Diazo ketones derived from N-p-tolylsulfonyl (tosyl)-protected áand â-amino acids have been synthesized and their diazo decomposition under standard Wolff rearrangement conditions, PhCO2Ag–Et3N–MeOH, has been investigated. It is observed that, under these conditions, several different reaction pathways, including direct carbene N]H insertion, are possible. The reaction is markedly affected by t...
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Due to the depletion of fossil fuels, biomass-derived sugars have attracted increasing attention in recent years as an alternative carbon source. Although significant advances have been reported in the development of catalysts for the conversion of carbohydrates into key chemicals (e.g., degradation approaches based on the dehydration of hydroxyl groups or cleavage of C-C bonds via retro-aldol ...
متن کاملAIEE active perylene bisimide supported mercury nanoparticles for synthesis of amides via aldoximes/ketoximes rearrangement.
Aggregates of perylene bisimide (PBI) derivative 3 serve as reactors and stabilizers for the preparation of mercury nanoparticles (HgNPs) which exhibit excellent catalytic efficiency in the conversion of aldoximes/ketoximes into primary/secondary amides via Beckmann rearrangement.
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2010
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja107329k