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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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Authors and Affiliations

  1. Institute of Organic Chemistry, Academy of Sciences of the Ukrainian SSR, 252660, Kiev

    E. D. Sych & L. T. Gorb

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  1. E. D. Sych
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  2. L. T. Gorb
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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/BF02401714

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  • DOI: https://doi.org/10.1007/BF02401714

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