P. Golubev, E.A. Karpova, A.S. Pankova, M. Sorokina, M.A. Kuznetsov
“Regioselective Synthesis of 7‑(Trimethylsilylethynyl) pyrazolo [1,5‑a] pyrimidines via Reaction of Pyrazolamines with Enynones”
J. Org. Chem., 2016, 81, 11268-11275
DOI:10.1021/acs.joc.6b02217
Condensation of enynones readily available from cheap starting material with pyrazolamines provides easy access to fluorescent 7-(trimethylsilylethynyl)pyrazolo[1,5-a]pyrimidines. The reaction is straightforward, does not require the use of any additional reagents or catalysts, and can be performed without inert atmosphere. Various substituents and functional groups in both enynone and pyrazolamine are tolerated. The presented method features full regioselectivity, high isolated yields, and simplicity of both setup and product purification. Fluorescent properties of the obtained pyrazolopyrimidines were studied.