Abstract
A variety of new pyrazolo[1,5-a]pyrimidines has been prepared as potential drugs for the treatment of insomnia. The general synthetic route used for this purpose involves the condensation of substituted cyanoacetamides 5a-c, prepared by reaction of cyanoacetic acid with amines in presence of acetic anhydride, with dimethylformamide dimethylacetal and subsequent treatment of the formed enamines 6 with hydrazine hydrate. This process affords the corresponding aminopyrazole carboxamides 9 that react with the enaminonitrile 12 to generate the targets. Structures of the substance prepared in these sequences were established by using spectroscopic methods, including N HMBC and NOE difference experiments, as well as X-raycrystallographic analysis.
Highlights
Almost 40% of adults between ages [40-70] suffer from insomnia at least one time during their lives
The results of the study described above have led to the development of a simple approach for synthesis of 5-aminopyrazole-4-carboxamides and methodology for the conversion of these compounds into pyrazolo[1,5-a]pyrimidines, substances that potentially interesting biological and medicinal properties
The observations made during this work showed that the reaction of hydrazine hydrate with enamines can afford cyanopyrazoles or aminopyrazoles, depending on the reaction conditions used
Summary
Almost 40% of adults between ages [40-70] suffer from insomnia at least one time during their lives.
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