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Synthesis of 7-hydroxy-2-(2-hydroxybenzoyl)benzo[c]chromen-6-ones by sequential application of domino reactions of 1,3-bis(silyl enol ethers) with benzopyrylium triflates |
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| Authors: | Mathias Lubbe Anke Flemming Peter Langer |
| Institution: | a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, D-18059 Rostock, Germany b Institut für Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany c Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, D-18059 Rostock, Germany |
| Abstract: | The domino, Michael-retro-Michael-aldol, reaction of 2,4-bis(trimethylsilyloxy)penta-1,3-diene with 3-formylchromones afforded 4-(2-hydroxybenzoyl)-2-acetylphenols, which were transformed into 6-(2-hydroxybenzoyl)chromones. The Me3SiOTf-mediated condensation of the latter with 1,3-bis(silyl enol ethers) and subsequent domino ‘retro-Michael-aldol-lactonization’ reaction afforded 7-hydroxy-2-(2-hydroxybenzoyl)benzoc]chromen-6-ones. |
| Keywords: | Chromones Cyclizations Domino reactions Oxygen heterocycles Silyl enol ethers |
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