Acrylamide in Rauhut-Currier reaction; intramolecular isomerization of activated alkenes for quinolone synthesis
| Autor: | Kishor Chandra Bharadwaj |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Chalcone
010405 organic chemistry Organic Chemistry Quinoline DABCO 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Rauhut–Currier reaction Intramolecular force Drug Discovery Organic chemistry Moiety Reactivity (chemistry) Isomerization |
| Zdroj: | Tetrahedron. 73:5690-5699 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.08.002 |
| Popis: | Acrylamides are fundamental Michael acceptors which have been used profoundly in synthetic, medicinal and polymer chemistry. However, due to their lower reactivity they have been least used in Morita-Baylis-Hillman (MBH) reaction and have been out of its vinylogus version Rauhut Currier (RC) reaction. Herein, use of acrylamide in RC reaction is being presented. Intramolecular RC reaction followed by [1,3]-H shift led to the synthesis of quinolone moiety. DABCO catalyzed IRC reaction of acrylamide at 80 °C in presence of water, was found to work on a number of precursors. En route chemo selective, gram scale method for ambiphilic, versatile precursor 2-amino chalcone is also reported. Chemoselective and economical conversion of 2-nitro chalcone to 2-aryl quinoline has also been developed. |
| Databáze: | OpenAIRE |
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