Abstract
The action of diazomethane on β-ethynylpyridines substituted in the pyridine ring or analogous compounds with an alkyl group in place of the acetylenic hydrogen atom has given 3-(pyridin-3-yl)pyrazoles. When the acetylenic hydrogen atom is replaced by an electron-accepting carboxyl group, the polarization of the triple bond interferes with the reaction, which then leads to a mixture of 3- and 4-(pyridin-3-yl)pyrazoles with the simultaneous methylation of the nitrogen of the pyrazole ring.
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Terent'ev, P.B., Moskvina, T.P., Moshentseva, L.V. et al. The addition of diazomethane to β-ethynylpyridines. Chem Heterocycl Compd 6, 460–464 (1970). https://doi.org/10.1007/BF00478392
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DOI: https://doi.org/10.1007/BF00478392