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Synthesis of 2-fluoro-1,4-benzoxazines and 2-fluoro-1,4-benzoxazepin-5-ones by exploring the nucleophilic vinylic substitution (SNV) reaction of gem-difluoroenamides

Tamara Meiresonne (UGent) , Guido Verniest (UGent) , Norbert De Kimpe (UGent) and Sven Mangelinckx (UGent)
(2015) JOURNAL OF ORGANIC CHEMISTRY. 80(10). p.5111-5124
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Abstract
N-Benzoyl beta,beta-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 beta-position of the enamide moiety endows unique electrophilic reactivity. Treatment of these enamides with oxygen nucleophiles gives rise to a nucleophilic vinylic substitution (SNV) 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, beta-addition of nucleophiles across the triple bond is observed also.
Keywords
5-ENDO-TRIG CYCLIZATION, F BOND-CLEAVAGE, ORGANIC-SYNTHESIS, YNAMIDES, DERIVATIVES, GENERATION, ETHERS, 1, 4-BENZOXAZINE, HETEROCYCLES, FORMAMIDES

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Chicago
Meiresonne, Tamara, Guido Verniest, Norbert De Kimpe, and Sven Mangelinckx. 2015. “Synthesis of 2-fluoro-1,4-benzoxazines and 2-fluoro-1,4-benzoxazepin-5-ones by Exploring the Nucleophilic Vinylic Substitution (SNV) Reaction of Gem-difluoroenamides.” Journal of Organic Chemistry 80 (10): 5111–5124.
APA
Meiresonne, T., Verniest, G., De Kimpe, N., & Mangelinckx, S. (2015). Synthesis of 2-fluoro-1,4-benzoxazines and 2-fluoro-1,4-benzoxazepin-5-ones by exploring the nucleophilic vinylic substitution (SNV) reaction of gem-difluoroenamides. JOURNAL OF ORGANIC CHEMISTRY, 80(10), 5111–5124.
Vancouver
1.
Meiresonne T, Verniest G, De Kimpe N, Mangelinckx S. Synthesis of 2-fluoro-1,4-benzoxazines and 2-fluoro-1,4-benzoxazepin-5-ones by exploring the nucleophilic vinylic substitution (SNV) reaction of gem-difluoroenamides. JOURNAL OF ORGANIC CHEMISTRY. 2015;80(10):5111–24.
MLA
Meiresonne, Tamara, Guido Verniest, Norbert De Kimpe, et al. “Synthesis of 2-fluoro-1,4-benzoxazines and 2-fluoro-1,4-benzoxazepin-5-ones by Exploring the Nucleophilic Vinylic Substitution (SNV) Reaction of Gem-difluoroenamides.” JOURNAL OF ORGANIC CHEMISTRY 80.10 (2015): 5111–5124. Print.
@article{6924378,
  abstract     = {N-Benzoyl beta,beta-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 beta-position of the enamide moiety endows unique electrophilic reactivity. Treatment of these enamides with oxygen nucleophiles gives rise to a nucleophilic vinylic substitution (SNV) 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, beta-addition of nucleophiles across the triple bond is observed also.},
  author       = {Meiresonne, Tamara and Verniest, Guido and De Kimpe, Norbert and Mangelinckx, Sven},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  language     = {eng},
  number       = {10},
  pages        = {5111--5124},
  title        = {Synthesis of 2-fluoro-1,4-benzoxazines and 2-fluoro-1,4-benzoxazepin-5-ones by exploring the nucleophilic vinylic substitution (SNV) reaction of gem-difluoroenamides},
  url          = {http://dx.doi.org/10.1021/acs.joc.5b00507},
  volume       = {80},
  year         = {2015},
}

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