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Reaction of 4-methyl-1,2-phenylenediamine with acetoacetic ester

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Depending on the reaction conditions, 4-methyl-1,2-phenylenediamine reacts with acetoacetic ester to form 4,7(or 8)-dimethyl-2,3-dihydro-1H-1,5-benzodiazepinones or 5(or 6)-methyl-1-isopropenylbenzimidazolones. During acid catalysis under mild conditions, the more basic diamine group initially reacts with acetoacetic ester to form ethyl 3-(2-amino-4-toluidino)-crotonate, which subsequently can be converted to the corresponding benzodiazepinone and 2,5-dimethylbenzimidazole.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, USSR

    A. N. Kost, Z. F. Solomko, N. M. Prikhod'ko & S. S. Teteryuk

  2. Dnepropetrovsk State University, USSR

    A. N. Kost, Z. F. Solomko, N. M. Prikhod'ko & S. S. Teteryuk

Authors
  1. A. N. Kost
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  2. Z. F. Solomko
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  3. N. M. Prikhod'ko
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  4. S. S. Teteryuk
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1556–1560, November, 1971.

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Kost, A.N., Solomko, Z.F., Prikhod'ko, N.M. et al. Reaction of 4-methyl-1,2-phenylenediamine with acetoacetic ester. Chem Heterocycl Compd 7, 1447–1451 (1971). https://doi.org/10.1007/BF00481117

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  • DOI: https://doi.org/10.1007/BF00481117

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