Abstract
Intramolecular cycloaddition of azaquinonoid-ketene (4) generated from benzotriazinone derivative to N, N-dimethylanilino group afforded unrearranged acridone in sharp contrast to a carbon analog series (1). Molecular orbital calculations and conformational studies using a model compound did not show much difference between azaquinonoid-ketene (11) and quinonoid-ketene (12), indicating similar propensity toward the [π4a+π2a] pathway of 4 in terms of FMO theory. These results led us to suggest the involvement of a concealed process in the transformation of 4 to unrearranged acridone (9), i. e., a [π4a+π2a] cycloaddition at the initial stage, by analogy with the carbon analog (1).
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