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-heteroar ylidene-2-oxindoles possessing tyrosine kinase inhibitory activity is described. Compounds 1-16 have been prepared by condensation of 2-oxin dole with a (hetero)aromatic aldehyde belonging to the naphthalene, te tralin, quinoline or indole series. The compounds so obtained were sin gle E or Z isomers or separable mixtures thereof. The single E or Z is omers could be partially transformed into their isomers by acid or bas ic catalysis. The E/Z configuration assignment was achieved by H-1 NMR spectroscopy on the basis of chemical shifts and NOE data obtained fr om NOESY spectra.