Synthesis of 1H-pyrano[4, 3-b]benzofuran-1-one derivatives via photochemical cyclization of substituted 4H-furo[3, 2-c]pyran-4-ones. Issue 44 (29th October 2020)

• Record Type: Journal Article
• Authors: Milyutin, Constantine V.; Lichitsky, Boris V.; Melekhina, Valeriya G.; Komogortsev, Andrey N.; Fakhrutdinov, Artem N.; Minyaev, Mikhail E.; Krayushkin, Michail M.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 44(2020)
• Publication Date: 2020-10-29
• Subjects: Photocyclization -- Intramolecular dehydration -- 4H-furo[3, 2-c]pyran-4-ones -- 1H-pyrano[4, 3-b]benzofuran-1-ones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152469
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new method for the synthesis of 1 H -pyrano[4, 3- b ]benzofuran-1-ones was developed. The process involve photochemical reaction of 4 H -furo[3, 2- c ]pyran-4-ones. Accessible starting materials, mild and environmentally friendly reaction conditions. Typical structure was confirmed by X-ray crystallographic analysis. Abstract: A novel approach for synthesis of fused 1 H -pyrano[4, 3- b ]benzofuran-1-ones was developed based on the photochemical reaction of 2, 3-disubstitued 4 H -furo[3, 2- c ]pyran-4-ones. The studied process includes the photocyclization of the hexatriene system and subsequent aromatization of benzene ring via elimination of water molecule. The structure of one of the 1 H -pyrano[4, 3- b ]benzofuran-1-one derivatives was determined by X-ray diffraction.