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Synthesis 2018; 50(07): 1439-1456
DOI: 10.1055/s-0036-1591537
DOI: 10.1055/s-0036-1591537
feature
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
The authors are indebted to the Research Foundation – Flanders (FWO, Project G0F4816N) and to the National Foundation for Science and Technology Development, Vietnam (NAFOSTED, Project FWO-104-2015.01) for financial support in the framework of a FWO-NAFOSTED bilateral research cooperation. The authors are also indebted to Ghent University – Belgium (Special Research Fund, BOF) for financial support.Further Information
Publication History
Received: 30 November 2017
Accepted after revision: 08 January 2018
Publication Date:
07 February 2018 (online)
Abstract
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 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)-β-lactam intermediates.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591537.
- Supporting Information
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