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Use of 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of trifluoromethyl-containing aminopropanes, 1,3-oxazinan-2-ones, aziridines, and 1,4-dioxan-2-ones

(2018) SYNTHESIS-STUTTGART. 50(7). p.1439-1456
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Abstract
3-Hydroxy-4-(trifluoromethyl)azetidin-2-ones were synthesized from the corresponding 3-benzyloxy--lactams and successfully transformed into new 3-chloro-4-(trifluoromethyl)azetidin-2-one building blocks. The latter chlorides were shown to be eligible precursors for the construction of CF3-containing aminopropanes, 1,3-oxazinanes, 1,3-oxazinan-2-ones, and aziridines. In addition, 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones proved to be interesting substrates for the synthesis of novel 3-[2,2,2-trifluoro-1-(arylamino)ethyl]-1,4-dioxan-2-ones via intramolecular cyclization of 3-(2-hydroxyethoxy)--lactam intermediates.
Keywords
BETA-LACTAMS, ASYMMETRIC-SYNTHESIS, ACID-DERIVATIVES, STEREOSELECTIVE-SYNTHESIS, AMINO-ACIDS, TRANSFORMATION, 1_3-OXAZINES, CYCLIZATION, AZETIDINES, CHLORIDE

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Chicago
Dao Thi, Hang, Giang Le Nhat Thuy, Saron Catak, Veronique Van Speybroeck, Tuyen Van Nguyen, and Matthias D’hooghe. 2018. “Use of 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones as Building Blocks for the Preparation of Trifluoromethyl-containing Aminopropanes, 1,3-oxazinan-2-ones, Aziridines, and 1,4-dioxan-2-ones.” Synthesis-stuttgart 50 (7): 1439–1456.
APA
Dao Thi, H., Le Nhat Thuy, G., Catak, S., Van Speybroeck, V., Van Nguyen, T., & D’hooghe, M. (2018). Use of 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of trifluoromethyl-containing aminopropanes, 1,3-oxazinan-2-ones, aziridines, and 1,4-dioxan-2-ones. SYNTHESIS-STUTTGART, 50(7), 1439–1456.
Vancouver
1.
Dao Thi H, Le Nhat Thuy G, Catak S, Van Speybroeck V, Van Nguyen T, D’hooghe M. Use of 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of trifluoromethyl-containing aminopropanes, 1,3-oxazinan-2-ones, aziridines, and 1,4-dioxan-2-ones. SYNTHESIS-STUTTGART. 2018;50(7):1439–56.
MLA
Dao Thi, Hang et al. “Use of 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones as Building Blocks for the Preparation of Trifluoromethyl-containing Aminopropanes, 1,3-oxazinan-2-ones, Aziridines, and 1,4-dioxan-2-ones.” SYNTHESIS-STUTTGART 50.7 (2018): 1439–1456. Print.
@article{8562397,
  abstract     = {3-Hydroxy-4-(trifluoromethyl)azetidin-2-ones were synthesized from the corresponding 3-benzyloxy--lactams and successfully transformed into new 3-chloro-4-(trifluoromethyl)azetidin-2-one building blocks. The latter chlorides were shown to be eligible precursors for the construction of CF3-containing aminopropanes, 1,3-oxazinanes, 1,3-oxazinan-2-ones, and aziridines. In addition, 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones proved to be interesting substrates for the synthesis of novel 3-[2,2,2-trifluoro-1-(arylamino)ethyl]-1,4-dioxan-2-ones via intramolecular cyclization of 3-(2-hydroxyethoxy)--lactam intermediates.},
  author       = {Dao Thi, Hang and Le Nhat Thuy, Giang and Catak, Saron and Van Speybroeck, Veronique and Van Nguyen, Tuyen and D'hooghe, Matthias},
  issn         = {0039-7881},
  journal      = {SYNTHESIS-STUTTGART},
  language     = {eng},
  number       = {7},
  pages        = {1439--1456},
  title        = {Use of 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones as building blocks for the preparation of trifluoromethyl-containing aminopropanes, 1,3-oxazinan-2-ones, aziridines, and 1,4-dioxan-2-ones},
  url          = {http://dx.doi.org/10.1055/s-0036-1591537},
  volume       = {50},
  year         = {2018},
}

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