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Mesoionic compounds with a bridged nitrogen atom. 3. Reactions of 2-[(1-methyl-2-pyridiniathio)acetyl]-thiazolo[3,2-a]pyridinium 3-oxide methylsulfate

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Abstract

The reactions of the product of cyclodehydration of (2-pyridylthio)acetic acid, viz., 2-[(1-methyl-2-pyridylthio)acetyl]thiazolo[3,2-a]pyridinium 3-oxide, were investigated. It is shown that its quaternary salt at the pyridine nitrogen atom in the presence of triethylamine acts as a nucleophile (by reactions at the methylene group with benzothiazolium and quinolinium sulfonatobetaines) and as an electrophile (by reaction with N-phenylrhodanine) with cleavage of both sulfide sulfur bonds with the simultaneous formation of a disulfide.

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Literature cited

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    L. T. Gorb, N. N. Romanov, and A. I. Tolmachev, Khim. Geterotsikl. Soedin., No. 10, 1343 (1979).

  2. 2.

    L. T. Gorb, N. N. Romanov, E. D. Sych, and A. I. Tolmachev, Dokl. Akad. Nauk Ukr. SSR, Ser. B, 895 (1978).

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    K. T. Potts and D. R. Choudhury, J. Org. Chem.,43, 2700 (1978).

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    L. T. Gorb, E. D. Sych, A. I. Tolmachev, and I. S. Shpileva, Khim. Geterotsikl. Soedin., No. 8, 1066 (1979).

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See [1] for communication 2.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 312–314, March, 1980.

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Sych, E.D., Gorb, L.T. Mesoionic compounds with a bridged nitrogen atom. 3. Reactions of 2-[(1-methyl-2-pyridiniathio)acetyl]-thiazolo[3,2-a]pyridinium 3-oxide methylsulfate. Chem Heterocycl Compd 16, 227–229 (1980). https://doi.org/10.1007/BF00553881

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Keywords

  • Sulfide
  • Pyridinium
  • Disulfide
  • Nitrogen Atom
  • Acetyl