Synthesis of 2-Fluoro-1,4-benzoxazines and 2-Fluoro-1,4-benzoxazepin-5-ones by Exploring the Nucleophilic Vinylic Substitution (S(N)V) Reaction of gem-Difluoroenamides
| Autor: | Norbert De Kimpe, Guido Verniest, Sven Mangelinckx, Tamara Meiresonne |
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| Přispěvatelé: | Department of Bio-engineering Sciences |
| Rok vydání: | 2015 |
| Předmět: |
Molecular Structure
Stereochemistry Organic Chemistry Substitution (logic) chemistry.chemical_element Fluorine Triple bond Medicinal chemistry Benzoxazines Organic Chemistry Phenomena chemistry.chemical_compound Oxazepines chemistry Nucleophile Electrophile Moiety Reactivity (chemistry) Organic synthesis |
| Zdroj: | The Journal of organic chemistry. 80(10) |
| ISSN: | 1520-6904 |
| Popis: | N-Benzoyl β,β-difluoroenamides and N-benzoyl fluoroynamides are novel structural units which have been explored as precursors in heterocyclic synthesis. The presence of two fluorine atoms at the β-position of the enamide moiety endows unique electrophilic reactivity. Treatment of these enamides with oxygen nucleophiles gives rise to a nucleophilic vinylic substitution (S(N)V) reaction, which was directed toward 2-fluoro-1,4-benzoxazines and 2-fluoro-1,4-benzoxazepin-5-ones. Furthermore, fluorinated ynamides, a new type of building block, were prepared in excellent yields for the first time. In this case, β-addition of nucleophiles across the triple bond is observed also. |
| Databáze: | OpenAIRE |
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