Abstract
The reactions of enamines with 2-oxoindolin-3-ylidene-acetates and -acetophenones have been studied. With enamines derived from aldehydes the former gave either 1,2- or 1,4-cycloaddition products, as previously described for the latter. However, both substrates gave only Michael-type adducts with enamines derived from cyclopentanone. The mechanism is discussed in terms of both frontier orbital interaction and stabilized dipolar intermediates.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
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