One-pot synthesis of 3-trifluoromethylbenzo[][1,4]oxazines from CF-imidoyl sulfoxonium ylides with 2-bromophenols

Herein, a method to access 3-trifluoromethyl-1,4-benzoxazines from CF 3 -imidoyl sulfoxonium ylides and 2-bromophenols has been demonstrated. This synthetic protocol proceeds via a one-pot two-step sequence that includes the lithium-bromide-promoted O-H insertion of sulfoxonium ylides and annulation...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2022-11, Vol.58 (89), p.12443-12446
Hauptverfasser: Pan, Mingshi, Tong, Yixin, Qiu, Xiaodong, Zeng, Xiaobao, Xiong, Biao
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Zusammenfassung:Herein, a method to access 3-trifluoromethyl-1,4-benzoxazines from CF 3 -imidoyl sulfoxonium ylides and 2-bromophenols has been demonstrated. This synthetic protocol proceeds via a one-pot two-step sequence that includes the lithium-bromide-promoted O-H insertion of sulfoxonium ylides and annulation, and has the merits of broad substrate scope, excellent functional tolerance and operational simplicity, which provides an alternative means of obtaining CF 3 -substituted heterocycles. A one-pot two-step fashion for the synthesis of 3-trifluoromethyl-1,4-benzoxazines from CF 3 -imidoyl sulfoxonium ylides and 2-bromophenols via lithium-bromide-promoted O-H insertion of sulfoxonium ylides and annulation has been demonstrated.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc04863a