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Issue 0, 1986
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Ring contraction of 1,2,6-thiadiazines to 1,2,5-thiadiazoles: synthesis of 2-substituted 4-amino-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxides

Abstract

Nitrosation of 2-substituted 2,3,5,6-tetrahydro-3,5-dioxo-1,2,6-thiadiazine 1,1-dioxides (2ad) yielded the corresponding 4-hydroxyimino derivatives (3ad), which by mild acid treatment were converted into 2-substituted 4-amino-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxides (4ad). A tentative mechanism is proposed. 2,6-Disubstituted 2,3,5,6-tetrahydro-3,5-dioxo-1,2,6-thiadiazine 1,1-dioxide (2e) also yielded the corresponding 4-hydroxyimino derivative (3e), but this compound does not react following the same pattern and under acid treatment, only the corresponding N,N′-disubstituted sulphamide (1e) was obtained.

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Article type: Paper
DOI: 10.1039/P19860000643
Citation: J. Chem. Soc., Perkin Trans. 1, 1986,0, 643-645
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    Ring contraction of 1,2,6-thiadiazines to 1,2,5-thiadiazoles: synthesis of 2-substituted 4-amino-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxides

    V. J. Arán, A. G. Bielsa, J. R. Ruiz and M. Stud, J. Chem. Soc., Perkin Trans. 1, 1986, 0, 643
    DOI: 10.1039/P19860000643

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