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Synthesis of New Pyrazolo[1,5-a]pyrimidines by Reaction of β,γ-Unsaturated γ-Alkoxy-α-keto Esters with N-Unsubstituted 5-Aminopyrazoles

Oleksandr O. Stepaniuk, Vitalii O. Matviienko, Ivan S. Kondratov*, Igor V. Vitruk, Andrei O. Tolmachev

*Institute of Bioorganic Chemistry and Petrochemistry, National Ukrainian Academy of Science, Murmanska 1, 02660 Kyiv-94, Ukraine, Email: vanya_komail.ru

O. O. Stepaniuk, V. O. Matviienko, I. S. Kontratov, I. V. Vitruk, A. O. Tolmachev, Synthesis, 2013, 45, 925-930.

DOI: 10.1055/s-0032-1318329 (free Supporting Information)


Abstract

The reaction of β,γ-unsaturated γ-alkoxy-α-keto esters with 5-aminopyrazoles proceeds with high regioselectivity to yield new pyrazolo[1,5-a]pyrimidines bearing an ester function in the 7-position. The obtained drug-like compounds have a great potential for medicinal chemistry as they closely resemble the structure of several marketed pharmaceuticals.

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Key Words

heterocycles, esters, regioselectivity, pyrazolo[1,5-a]pyrimidines, 5-aminopyrazoles, benzo-fused N-heterocycles


ID: J66-Y2013-0730