Stereoselective synthesis of 9-vinyl substituted unsymmetrical xanthenes and thioxanthenes

[Display omitted] •E-selective 9-vinyl novel unsymmetrical xanthene/thioxanthene synthesis.•Novel quinoline fused xanthene synthesis.•Lewis acid catalyzed cyclization of π-activated allylic alcohols.•High yielding reactions. Activated 2°-allylic alcohols derived from 2-aryloxybenzaldehydes and 2-(ar...

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Veröffentlicht in:Tetrahedron letters 2020-09, Vol.61 (37), p.152347, Article 152347
Hauptverfasser: Prajapati, Anamika, Kumar, Mahendra, Thakuria, Ranjit, Basak, Ashok K.
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] •E-selective 9-vinyl novel unsymmetrical xanthene/thioxanthene synthesis.•Novel quinoline fused xanthene synthesis.•Lewis acid catalyzed cyclization of π-activated allylic alcohols.•High yielding reactions. Activated 2°-allylic alcohols derived from 2-aryloxybenzaldehydes and 2-(arythio)benzaldehydes undergo intramolecular Friedel-Crafts alkylation reaction when heated with catalytic amount of a Lewis acid in 1,2-dichloroethane to provide highly E-selective 9-vinyl substituted unsymmetrical novel xanthenes and thioxanthenes in good yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152347