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Using pyrazolones and amino pyrazole as precursors, many pyranopyrazole and bis-pyrazole derivatives were prepared. Among these, the following pyranopyrazoles have been synthesized by three components, one pot condensation reactions of aryl aldehydes, malononitrile and 3-Methyl-1-Phenyl pyrazoline-5-one: In case of bis-pyrazoles, two different synthetic approaches have been investigated. One with arylaldehydes and active methylene compounds (cyanoacetamide, ethyl cyanoacetate or diethyl malonate) using triethylamine as base. In second approach, (Z)-2-cyano-3-arylacrylamide reacts with two moles of 3-Methyl-1-Phenyl pyrazoline-5-one to give the bis-pyrazole derivatives
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