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Benzo[1,2-d:3,4-d′] diimidazole derivatives

III. Reaction of 3,6-dimethyl- and 2,3,6,7-tetramethylbenzo[1,2-d: 3,4-d′]diimidazole with electrophilic reagents

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Abstract

Bromination of 3,6-dimethylbenzo[1,2-d:3,4-d′]diimidazole (Ia) in chloroform with bromine and dioxane dibromide in dioxane leads, through the intermediate formation of perbromides, to the 4-bromo-substituted derivative; 4,5-dibromo-3,6-dimethylbenzo[1,2-d:3,4-d′]dimidazole is formed in addition to a monobromo-substituted derivative by the action of potassium bromate in hydrobromic acid on Ia. Nitration of Ia and its 2,7-dimethyl-substituted derivative (Ib), even under severe conditions, leads to the 4-mononitro derivatives. Only one of the pyridine nitrogen atoms is quaternized by the action of excess methyl iodide on Ia, b.

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Literature cited

  1. Yu. V. Koshchienko, A. M. Simonov, and A. F. Pozharskii, Khim. Geterotsikl. Soedin., 1132 (1971).

  2. L. Fieser, Chemistry of Phenanthrene Derivatives [Russian translation], Goskhimizdat (1941), p. 19.

  3. L. S. Éfros, L. N. Kononova, and Ya. Éded, Zh. Obshch. Khim., 24, 488 (1954).

    Google Scholar 

  4. S. S. Kolodyazhnaya and A. M. Simonov, Khim. Geterotsikl. Soedin., 714 (1969).

  5. S. F. Torf and N. V. Khromov-Borisov, Zh. Obshch. Khim., 30, 1798 (1960).

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See [1] for communication II.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 107–110, January, 1973.

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Simonov, A.M., Koshchienko, Y.V. & Belenko, T.G. Benzo[1,2-d:3,4-d′] diimidazole derivatives. Chem Heterocycl Compd 9, 95–98 (1973). https://doi.org/10.1007/BF00476161

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  • DOI: https://doi.org/10.1007/BF00476161

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