Three-component condensation of 4-piperidinones (7), 5-pyrazolones (8), and malononitrile (4) proceeds chemically and electrochemically and is a convenient one-step means of synthesis of substituted 6-amino-5-cyanospiro-4-(piperidine-4')-2H,4H-dihydropyrazolo[3,4-b]pyrans (12). The electrochemical reactions proceed under milder conditions and with yields 12-15% greater than those of the reactions catalyzed by chemical bases.
2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles. -The potentially physiologically active title compounds (IV) are prepared by a three-component condensation reaction using three different methods. The electrochemical method is more regioselective and gives analytically pure products which do not require further recrystallization. -(SHESTOPALOV, A. M.; EMELIYANOVA, Y. M.; SHESTOPALOV, A. A.; RODINOVSKAYA, L. A.; NIAZIMBETOVA, Z. I.; EVANS*, D. H.; Tetrahedron 59 (2003) 38, 7491-7496; Dep. Chem. Biochem., Univ. Del., Newark, DE 19716, USA; Eng.) -Kieslich 01-103
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