Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction
Russian Journal of General Chemistry(2020)
Abstract
The effect of electronic properties of substituents in the reactants on the [4+2]-cycloaddition of 3-vinyl-chromen-4-ones (dienes) and N -vinylpyrrolidines (dienophiles) has been studied. The conditions determining the formation of 4,4a-dihydroxanthones or benzophenones as the major products have been found. The aromatization of 4,4a-dihydroxanthones via pyran ring opening has been interpreted by quantum chemical calculations. A wide series of new 4,4a-dihydroxanthone and benzophenone derivatives have been isolated.
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Key words
[4+2]-cycloaddition, 3-vinylchromones, enamines, 4,4a-dihydroxanthones, benzophenone
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