A novel entry to xanthones by an intramolecular Diels-Alder reaction involving 2-(1, 2-dichlorovinyloxy) aryl dienones. Issue 39 (27th September 2018)

• Record Type: Journal Article
• Authors: Otrubova, Katerina; Fitzgerald, Anne E.; Mani, Neelakandha S.
• Is Part Of: Tetrahedron. Volume 74:Issue 39(2018)
• Page Start: 5715
• Page End: 5724
• Publication Date: 2018-09-27
• Subjects: Xanthone synthesis -- 2-(1, 2-dichlorovinyloxy) aryl dienones -- Intramolecular Diels Alder reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.08.007
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A wide array of synthetic methods are described in the literature for the preparation of xanthones—a prominent class of tricyclic molecules that occur widely in nature. Majority of these reported methods involve linking the two aromatic rings and forming the central pyrone ring using a variety of classical and non-classical cyclization strategies. In a conceptually different approach, we describe here a new xanthone synthesis wherein both the pyrone and the second aromatic rings were forged in a single step by an intramolecular cycloaddition reaction involving 2-(1, 2-dichlorovinyloxy) aryldienones. Graphical abstract: Image 1