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Synthesis and lactim-lactam tautomerism of 1,2-dihydrofuro[2,3-b]quinol-4-one derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of O-ethylbutyrolactonium tetrafluoroborate with derivatives of ethyl anthranilate was used to synthesize tetrafluoroborates of cyclic imido esters, which were cyclized to furo[2,3-b]quinol-4-one derivatives by heating in a solution of sodium ethoxide. A number of N- and O-alkyl derivatives were obtained by alkylation of these compounds. The tautomerism of 6-chloro- and 7-chloro-2,3-dihydrofuro [2,3-b]quinol-4-ones that are unsubstituted in the benzene ring was studied, and a dependence of the position of the tautomeric equilibrium on the solvent and the substituent in the benzene ring was established.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 376–381, March, 1984.

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Peresleni, E.M., Marchenko, N.B., Anisimova, O.S. et al. Synthesis and lactim-lactam tautomerism of 1,2-dihydrofuro[2,3-b]quinol-4-one derivatives. Chem Heterocycl Compd 20, 304–309 (1984). https://doi.org/10.1007/BF00515645

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  • DOI: https://doi.org/10.1007/BF00515645

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