Chemistry of Heterocyclic Compounds

, Volume 1, Issue 3, pp 233–236 | Cite as

Investigations on 2, 1, 3-thia- and selenadiazoles

XXXVIII. Derivatives of 5-methyl-4-hydroxy- and 4-ethoxybenzo-2, 1, 3-thiadiazoles
  • V. G. Pesin
  • I. A. Belen'kaya-Lotsmanenko
Article
  • 54 Downloads

Abstract

Nitration and nitrosation of 4-hydroxy-5-methyl-benzo-2, 1, 3-thiadiazole gives 4-hydroxy-5-methyl-7-nitro-and 4-hydroxy-5-methyl-7-nitrosobenzo-2, 1, 3-thiadiazoles. Oxidation of the latter, or of 4,7-diamino-5-methylbenzo-2,1,3-thiadiazole gives 5-methyl-4,7-dihydroxy-2, 1, 3-thiadiazole, forming derivatives with sodium bisulfite or hydroxylamine, and reduced by sodium dithionite to 5-methyl-4, 7-dihydroxybenzo-2, 1, 3-thiadiazole. The latter is also obtained by diazotizing 5-methyl-4-hydroxy-7-aminobenzo-2, 1, 3-thiadiazole, and decomposing the diazonium salt. Nitration of 4-ethoxybenzo-2, 1, 3-thiadiazole with sodium ethoxide gives 4-ethoxy-7-aminobenzo-2, 1, 3-thiadiazole, acetylated to 4-ethoxy-7-acetaminobenzo-2, 1, 3-thiadiazole.

Keywords

Oxidation Sodium Organic Chemistry Nitration Hydroxylamine 

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References

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    V. G. Pesin, I; A. Belen'kaya-Lotsmanenko, and A. M. Khaletskii, ZhOKh, 34, 3763, 1964.Google Scholar
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    V. G. Pesin, A. M Khaletskii, and I. A. Lotsmanenko, ZhOKh, 33, 1746, 1963.Google Scholar

Copyright information

© The Faraday Press, Inc. 1966

Authors and Affiliations

  • V. G. Pesin
    • 1
  • I. A. Belen'kaya-Lotsmanenko
    • 1
  1. 1.Leningrad Chemical-Pharmaceutical InstituteUSSR

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