4-Chloro-1,8-naphthyridines and 4-chloro-6,8-dimethyl-1,7-naphthyridine rearrange on treatment with hydrazine hydrate in a sealed tube at 150 °C to give pyrazol-5-ylpyridines. The products undergo cyclisation with triethyl orthoesters and with cyclohexanone to form new ring systems, pyrazolo[1,5-c]pyrido-[3,2-e]- and -[4,3-e]-pyrimidines.
R. A. Bowie, M. J. C. Mullan and J. F. Unsworth, J. Chem. Soc., Perkin Trans. 1, 1972, 1106 DOI: 10.1039/P19720001106
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