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Lactam and amide acetals. 69. Synthesis and properties of 3-(aminomethylene)-2-indolinone derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

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.

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry, 119021, Moscow

    T. V. Golovko, N. P. Solov'eva, G. A. Bogdanova, Yu. N. Sheinker & V. G. Granik

Authors
  1. T. V. Golovko
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  2. N. P. Solov'eva
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  3. G. A. Bogdanova
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  4. Yu. N. Sheinker
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  5. V. G. Granik
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Additional information

For Communication 68, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1190–1198, September, 1991.

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Golovko, T.V., Solov'eva, N.P., Bogdanova, G.A. et al. Lactam and amide acetals. 69. Synthesis and properties of 3-(aminomethylene)-2-indolinone derivatives. Chem Heterocycl Compd 27, 952–959 (1991). https://doi.org/10.1007/BF00484357

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  • DOI: https://doi.org/10.1007/BF00484357

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