LACTAM AND AMIDE ACETALS. 69. SYNTHESIS AND PROPERTIES OF 3-(AMINOMETHYLENE)-2-INDOLINONE DERIVATIVES

Article abstract of DOI:10.1007/BF00484357

Oxindole derivatives reacted with the diethyl acetals of dimethylformamide and dimethylacetamide to give the corresponding derivatives of 3-(aminomethylene)-, (aminoethylidene)-, and (ethoxyethylidene)-2-indolinone.These products were then easily converted to N-aryl- and N-alkylaminomethyleneoxindoles upon treatment with aryl or alkyl amines.The alkylation of N,N-dimethylaminomethylene-2-indolinones by dimethyl sulfate and triethyloxonium tetrafluoroborate, and the reactions of the resulting methyl sulfates and tetrafluoroborates with nucleophilic reagents were studied.The configuration of the 3-(aminomethylene)-2-indolinone derivatives prepared at the enamine C=C double bond was investigated by NMR.The free energies of activation for the cis-trans isomerization were determined in a number of cases.