Methyl azido(phenylhydrazono)acetate (1) reacts with variously substituted enamines (4)–(7) to give product mixtures including 1,4,5,6-tetrahydro-1,2,4-triazines (8)–(13) and 1,2,4-triazoles (14)–(16). A mechanism is proposed involving a preliminary 1,3-dipolar cycloaddition to give unstable Δ2-1,2,3-triazolines (17).
L. Bruché, L. Garanti and G. Zecchi, J. Chem. Soc., Perkin Trans. 1, 1984, 1427 DOI: 10.1039/P19840001427
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