Microwave-Assisted, Asymmetric Synthesis of 3-Amino-2,3-Dihydrobenzofuran Flavonoid Derivatives from Chalcones
| Autor: | Yash R. Mehta, Lianyan L. Xu, Leslie N. Aldrich, Travis R. Helgren, Ivan Pavlinov, Melissa A. Korkmaz, Daniel Sotelo |
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| Rok vydání: | 2017 |
| Předmět: |
Flavonoids
Chalcone Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Enantioselective synthesis Regioselectivity Epoxide General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Chalcones Microwave chemistry Nucleophilic aromatic substitution Humans Aldol condensation Organic synthesis Microwaves Benzofurans |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 24(18) |
| ISSN: | 1521-3765 |
| Popis: | A route to access 3-amino-2,3-dihydrobenzofurans that utilizes microwave-assisted organic synthesis to rapidly generate analogues has been developed. The route begins with an acid-catalyzed, microwave-assisted aldol condensation to generate chalcone intermediates, followed by a Corey-Bakshi-Shibata reduction and subsequent Sharpless asymmetric epoxidation to access stereoisomeric epoxyalcohols. The final step is a one-pot, microwave-assisted, regioselective, acid-catalyzed epoxide opening with various amines followed by an intramolecular nucleophilic aromatic substitution reaction to generate the 3-amino-2,3-dihydrobenzofurans. This route provides ready access to stereochemically and structurally diverse analogues of these flavonoid scaffolds. Additionally, a pilot library was synthesized, and the biological activity diversity of the chalcones and dihydrobenzofurans was explored in human carcinoma cell lines. |
| Databáze: | OpenAIRE |
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