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Reactions of ortho-substituted benzanilides and related heterocyclic compounds in aqueous sulfuric acid solution

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

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Conclusions

  1. 1.

    Hydrolysis of o-aminobenzanilide, N-benzoylanthranilic acid, and 2-phenyl-4H-3,1-benzoxazinone in sulfuric acid follows a mechanism in which the limiting step is hydrated-proton attack on the unprotonated (ester) amide bond. Carbonyl protonation leads to the formation of an inactive form.

  2. 2.

    Cyclization of o-aminobenzanilide is catalyzed by intramolecular protonation of the primary amino group. A mechanism for the cyclization of N-benzoylanthranilic acid is proposed.

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Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow

    A. I. Donskikh, V. N. Kulagin, T. E. Nenasheva, Yu. V. Moiseev, G. E. Zaikov & G. M. Tseitlin

  2. D. I. Mendeleev Moscow Institute of Chemical Technology, USSR

    A. I. Donskikh, V. N. Kulagin, T. E. Nenasheva, Yu. V. Moiseev, G. E. Zaikov & G. M. Tseitlin

Authors
  1. A. I. Donskikh
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  2. V. N. Kulagin
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  3. T. E. Nenasheva
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  4. Yu. V. Moiseev
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  5. G. E. Zaikov
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  6. G. M. Tseitlin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 562–568, March, 1978.

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Donskikh, A.I., Kulagin, V.N., Nenasheva, T.E. et al. Reactions of ortho-substituted benzanilides and related heterocyclic compounds in aqueous sulfuric acid solution. Russ Chem Bull 27, 484–489 (1978). https://doi.org/10.1007/BF00923921

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  • DOI: https://doi.org/10.1007/BF00923921

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