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Year 2005, Month 12 (Section Full Articles, Page 2846)

Synthesis and some properties of 6-di(tri)f luoromethyl- and 5-di(tri)f luoroacetyl-3-methyl-1-phenylpyrano[2,3-c]pyrazol-4(1H)-ones

V. Ya. Sosnovskikh, M. A. Barabanov, B. I. Usachev, R. A. Irgashev, and V. S. Moshkin

Condensation of 4-acetyl-5-hydroxy-3-methyl-1-phenylpyrazole with RFCO2Et (RF = CF2H, CF3) in the presence of LiH affords 4-di(tri)fluoroacetoacetyl-5-hydroxy-3-methyl-1-phenylpyrazoles from which 6-di(tri)fluoromethyl- and 5-di(tri)fluoroacetyl-3-methyl-1-phenylpyrano[2,3-c]pyrazol-4(1H )-ones were synthesized. The reactions of pyranopyrazoles with hydrazine hydrate, ethyl mercaptoacetate, or aromatic amines proceed at the C(6) atom with pyrone ring opening and formation of aminoenones, pyrazoles, or thiophenes with the 5-hydroxy-3-methyl-1-phenyl-4-pyrazolyl fragment.

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