Base-catalysed condensation of 3,4-dihydrobenz[cd]indol-5-(1H)-one (1) with aromatic aldehydes gives 4-arylmethylene-3,4-dihydrobenz[cd]indol-5(1H)-ones (11) and 4-benzylbenz[cd]indol-5(1H)-ones (12); the former are converted into the latter by acid. Spectroscopic studies indicate that the latter compounds exist, in solution, as the uncharged quinone methides, rather than as the aromatic zwitterion forms.
G. M. Buchan and A. B. Turner, J. Chem. Soc., Perkin Trans. 1, 1975, 2257 DOI: 10.1039/P19750002257
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