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

Dao Thi, Hang; Le Nhat Thuy, Giang; ÇATAK, ŞARON; Van Speybroeck, Veronique; Van Nguyen, Tuyen; D'Hooghe, Matthias

doi:10.1055/s-0036-1591537

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

Dao Thi H., Le Nhat Thuy G., ÇATAK Ş., Van Speybroeck V., Van Nguyen T., D'Hooghe M.

Synthesis (Germany), cilt.50, sa.7, ss.1439-1456, 2018 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 50 Sayı: 7
Basım Tarihi: 2018
Doi Numarası: 10.1055/s-0036-1591537
Dergi Adı: Synthesis (Germany)
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.1439-1456
Boğaziçi Üniversitesi Adresli: Evet

Özet

3-Hydroxy-4-(trifluoromethyl)azetidin-2-ones were synthesized from the corresponding 3-benzyloxy-β-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 CF 3 -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)-β-lactam intermediates.