Synthesis and configuration of some new bicyclic 3-arylidene-2-oxindoles and 3-heterotarylidene-2-oxindoles

The synthesis of a novel class of bicyclic 3-arylidene- and 3-heteroarylidene-2-oxindoles possessing tyrosine kinase inhibitory activity is described. Compounds 1-16 have been prepared by condensation of 2-oxindole with a (hetero)aromatic aldehyde belonging to the naphthalene, tetralin, quinoline or indole series. The compounds so obtained were single E or Z isomers or separable mixtures thereof. The single E or Z isomers could be partially transformed into their isomers by acid or basic catalysis. The E/Z configuration assignment was achieved by H-1 NMR spectroscopy on the basis of chemical shifts and NOE data obtained from NOESY spectra.