Trifluoromethylated morpholines condensed with oxetane: Synthesis and transformations

[Display omitted] •A simple one-pot, atom and steps economic (PASE) synthesis of trifluoromethylated morpholines condensed with oxazine or oxetane rings has been elaborated.•The assembly of heterocycles from fluorinated α-bromoenones and amino diols is initiated by aza-Michael reaction.•Unexpected i...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2019-11, Vol.227, p.109366, Article 109366
Main Authors: Rulev, Alexander Yu, Romanov, Alexey R., Kondrashov, Evgeniy V., Ushakov, Igor A., Muzalevskiy, Vasiliy M., Nenajdenko, Valentine G.
Format: Article
Language:English
Subjects:
Chloroform
Condensed bicycles
Diols
Fluorinated azaheterocycles
Isomerization
Morpholine
Oxetane
Room temperature
Trifluoromethyl group
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Summary:[Display omitted] •A simple one-pot, atom and steps economic (PASE) synthesis of trifluoromethylated morpholines condensed with oxazine or oxetane rings has been elaborated.•The assembly of heterocycles from fluorinated α-bromoenones and amino diols is initiated by aza-Michael reaction.•Unexpected isomerization of oxetane-bearing heterocycles into bis-oxazines was found. •The treatment of fluorinated α-bromoenones with amino diols leads mainly to bicyclic compounds bearing condensed morpholine and oxetane rings. These derivatives undergo spontaneous isomerization into bis-oxazines when standing in a chloroform solution at room temperature.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2019.109366