Heterodiene synthesis. Part XVII. Reactions of 2-oxoindolin-3-ylidene derivatives with enamines: a Michael pathway as an alternative to 1,2- and 1,4-cycloadditions
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 17,p. 1872-1879
- https://doi.org/10.1039/p19760001872
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.Keywords
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