o-Vinylphenylhydrazonyl chlorides (2) react with triethylamine in boiling benzene to afford cyclopropa-[c]cinnolines (4) and [1,2,4]triazolo[1,5-a]quinolines (5). Under the same conditions, the structurally related compounds (7) give 1,2-benzodiazepines (10). A mechanism is proposed involving nitrile imine intermediates which cyclise through participation of the nitrile or ethylenic group.
L. Bruché, L. Garanti and G. Zecchi, J. Chem. Soc., Perkin Trans. 1, 1983, 539 DOI: 10.1039/P19830000539
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