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Investigations in heterocyclic chemistry

XLIV. Comparative ease of ring-closure of five- and six-membered heterocycles in the acid condensation of arylides of diarylglycolic acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

With the acid condensation of diarylglycolic benzylanilides as an example, it has been shown that the predominant formation of a fivemembered ring rather than a six-membered ring takes place even in the case where the internal structure of the anilide permits the simultaneous formation of both rings. It has also been shown that it is possible to determine the size of the ring formed on condensation from the UV and IR spectra, and the presence of hydrogen bonds in the arylamides of diarylglycolic acids and the formation of the lactim form and of the quatenary ammonium salt of the base of 3, 3-diphenyloxindole in solutions of sodium ethoxide and concentrated H2SO4, respectively, have been confirmed.

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Authors and Affiliations

  1. Khar'kov Pharmaceutical Institute, USSR

    P. A. Petyunin, A. K. Sukhomlinov & N. G. Panferova

  2. Perm Pharmaceutical Institute, USSR

    P. A. Petyunin, A. K. Sukhomlinov & N. G. Panferova

Authors
  1. P. A. Petyunin
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  2. A. K. Sukhomlinov
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  3. N. G. Panferova
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Additional information

For part XLIII, see [17].

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Petyunin, P.A., Sukhomlinov, A.K. & Panferova, N.G. Investigations in heterocyclic chemistry. Chem Heterocycl Compd 4, 748–752 (1968). https://doi.org/10.1007/BF00486949

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  • DOI: https://doi.org/10.1007/BF00486949

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