Photoinduced reactions—LXXI: Photorearrangement of 3-hydroxyflavones to 3-aryl-3-hydroxy-1,2-indandiones |
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| Authors: | T Matsuura T Takemoto R Nakashima |
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| Institution: | Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto 606, Japan |
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| Abstract: | 3-Hydroxyflavones (1) were found to undergo a novel photorearrangement to 3-aryl-3-hydroxy-1,2-indandiones (2) which were characterized as o-phenylenediamine adducts, 1-aryl-1-hydroxy-11H-indeno1,2-b]quinoxalines (3). To the contrary, 3-methoxyflavone underwent photochemical intramolecular hydrogen transfer. Photochemical reactivities of several other flavonoids were examined. It appears that the 5-hydroxyl H-bonded to the 4-carbonyl causes photoresistance in flavonoids. |
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