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Fries reaction and dakin rearrangement in benzo-2,1,3-thiadiazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The Fries rearrangement of 4- and 5-acetoxybenzo-2,1,3-thiadiazoles has given 4-hydroxy-7-acetyl- and 5-hydroxy-4-acetylbenzo-2,1,3-thiadiazoles, which on oxidation afford mixtures of 5-chloro-4,7-dioxo- and 5,6-dichloro-4,7-dioxobenzo-2,1,3-thiadiazole and of 6-chloro-4,5-dioxo- and 6,7-dichloro-4,5-dioxobenzo-2,1,3-thiadiazole. Reaction of 6,7-dichloro-4,5-dioxobenzo-2,1,3-thiadizole with ortho-phenyl-enediamine gives 4,5-dichloro-2,1,3-thiadiazolo[4,5-a]phenazine.

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Literature Cited

  1. I. A. Belen'kaya, G. P. Krokhina, V. é. Vignevich, V. P. Lozitskii, O. G. Yasinskaya, and V. V. Ivanova, Khim.-Farm. Zh., No. 1, 46 (1985).

    Google Scholar 

  2. I. A. Belen'kaya, G. P. Krokhina, and S. A. Andronati, Khim. Geterotsikl. Soedin., No. 10, 1344 (1982).

    Google Scholar 

  3. I. A. Belen'kaya, G. P. Krokhina, S. A. Andronati, K. A. Abramova, and T. D. Panasyuk, Author's Cert. (USSR) No. 1,087,521; Byull. Izobret., No. 15, 86 (1984).

  4. I. A. Belen'kaya, N. P. Chizhov, and N. G. Chigareva, Khim.-Farm. Zh., No. 8, 66 (1978).

    Google Scholar 

  5. B. A. Kazanskii, I. L. Knunyants, M. M. Shemyakin, and N. N. Mel'nikov (editors), Reactions and Methods of Study of Organic Compounds [in Russian], GONTI, Moscow (1961), Vol. 10, p. 78.

    Google Scholar 

  6. I. A. Belen'kaya and G. P. Krokhina, Author's Cert. (USSR), No. 932,801; Byull. Izobret., No. 4, 344 (1983).

  7. I. A. Belen'kaya, G. P. Krokhina, and S. A. Andronati, Khim. Geterotsikl. Soedin., No. 6, 850 (1987).

    Google Scholar 

  8. V. G. Pesin, I. A. Belen'kaya-Lotsmanenko, and A. M. Khaletskii, Zh. Org. Khim., 34, 3763 (1964).

    Google Scholar 

  9. N. N. Mel'nikov, The Chemistry and Technology of Pesticides [in Russian], Khimiya, Moscow (1974), p. 172.

    Google Scholar 

  10. L. S. éfros and R. M. Levit, Zh. Org. Khim., 25, 199 (1955).

    Google Scholar 

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Authors and Affiliations

  1. A. V. Bogatskii Institute of Physical Chemistry, Academy of Sciences of the Ukrainian SSR, 270080, Odessa

    I. A. Belen'kaya, G. P. Krokhina, S. A. Sirik & S. A. Andronati

Authors
  1. I. A. Belen'kaya
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  2. G. P. Krokhina
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  3. S. A. Sirik
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  4. S. A. Andronati
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1683–1687, December, 1987.

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Belen'kaya, I.A., Krokhina, G.P., Sirik, S.A. et al. Fries reaction and dakin rearrangement in benzo-2,1,3-thiadiazoles. Chem Heterocycl Compd 23, 1356–1359 (1987). https://doi.org/10.1007/BF00472265

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  • DOI: https://doi.org/10.1007/BF00472265

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