With difunctional nucleophiles, N-[alkoxy(methylthio)methylene]carbamates undergo cyclisation either in the 1,3- or in the 3,3-sense. The former type of reaction (reagents in parentheses) gives 1,2,4-triazol-5-ones (hydrazine), 1,2,4-oxadiazol-5-ones (hydroxylamine), and 1,3,5-triazin-2-ones (guanidines). 3,3-Cyclisation (diamines) provides a novel and mild route to cyclic guanidines.
P. R. Atkins, S. E. J. Glue and I. T. Kay, J. Chem. Soc., Perkin Trans. 1, 1973, 2644 DOI: 10.1039/P19730002644
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