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Synthesis and investigation of the chemical and physicochemical properties of 6-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2,3-dihydro-2-indolinones

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Abstract

Acylation of 1-ethyl-3-(N,N-dimethyl)aminomethylene-1,2-dihydro-2-indolinone by succinic anhydride in the presence of aluminum chloride has been studied. PMR spectroscopy shows that this acylation leads to formation of a mixture of the 5- and 6-succinoyl derivatives with predominance of the latter (cis and trans isomers of both these products were found). The reaction of the latter with hydrazine hydrate gives hydrazinomethylene derivative of 2-indolinone, in reaction of which with various carbonyl compounds a series of oxindol hydrazones has been obtained. The reaction of these products with primary amines smoothly leads to transamination and the formation of enamines of 1,6-disubstituted 2-indolinone.

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Authors
  1. T. V. Golovko
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  2. N. P. Solov'eva
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  3. O. S. Anisimova
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  4. V. G. Granik
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Additional information

NIOPIK Russian Federation State Science Center, 103787 Moscow, Russia and TsKhLS-VNIKhFI, 119815 Moscow, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1347–1355, October, 1999.

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Golovko, T.V., Solov'eva, N.P., Anisimova, O.S. et al. Synthesis and investigation of the chemical and physicochemical properties of 6-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2,3-dihydro-2-indolinones. Chem Heterocycl Compd 35, 1167–1175 (1999). https://doi.org/10.1007/BF02323374

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  • DOI: https://doi.org/10.1007/BF02323374

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