24061-06-1Relevant articles and documents
Diels-Alder reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethane. New synthesis of benzo[b]xanthones
Sandulache, Angela,Silva, Artur M.S,Cavaleiro, José A.S
, p. 105 - 114 (2007/10/03)
An efficient new route to the benzo[b]xanthone system has been developed and applied to the synthesis of several new derivatives. The cycloaddition reactions of chromone-3-carboxaldehydes 12, reacting as dienophiles, with ortho-benzoquinodimethane 7 gave a diastereomeric mixture of cycloadducts 8 and 9. The formation of these compounds results from the Diels-Alder reactions of 12 and 7 followed by the in situ deformylation. The oxidation of adducts 8 and 9 with dimethyl sulfoxide in the presence of iodine gave the novel benzo[b]xanthones 11 in good yields.