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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp.371-383
Published online, 27th December, 2010
DOI: 10.3987/COM-10-12101
The Synthesis of Some Derivatives Based on the 4-Benzyl-1H-pyrazole-3,5-diamine Core

Lukáš Jedinák, Vladimír Kryštof, and Petr Cankař*

*Department of Organic Chemistry, Palacký University, Trida Svobody 8, 77146 Olomouc, Czech Republic

Abstract

The three-step synthesis of 4-benzyl-1H-pyrazole-3,5-diamines 2 from commercially available aldehydes 3 is given. The Knoevenagel condensation was utilized to assemble the initial carbon framework, resulting in the benzylidenemalononitriles 4 which were directly transformed by the reduction of the electron deficient C=C bond to benzylmalononitriles 5. Subsequent cycloaddition of hydrazine with 5 afforded the desired pyrazoles 2. Due to the high similarity with 4-arylazo-1H-pyrazole-3,5-diamines, the biological activities of the 4-benzyl-1H-pyrazole-3,5-diamines 2 were evaluated while focusing on the inhibition of cyclin-dependent kinases (CDKs), but no significant results were obtained.