Organic azides, bearing a nitrite function at the γ- or δ-position, react with acyl isothiocyanates to give fused dihydro-1,2,4-thiadiazolimines. Representative examples are given. In the case of 2-cyanobenzyl azide and benzoyl isothiocyanate, the formation of 9b is accompanied by two side products, 15 and 16. Mechanisms are presented to explain the formation of the products.
G. L'abbé, I. Sannen and W. Dehaen, J. Chem. Soc., Perkin Trans. 1, 1993, 27 DOI: 10.1039/P19930000027
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