Despite prior reports of several really effective catalytic and non-catalytic approaches towards Biginelli's 3,4-dihydropyrimidin-2(1H)-ones, an overwhelming number of new catalysts for the Biginelli reaction have been recently published. Most of the catalysts are somewhat exotic, expensive, harmful and even uneffective in the absence of acidic additives. Herein we reduce the "yet-another-one-catalyst" idea to absurdity by proposing NaCl promotes the reaction that actually requires no catalyst, neither rare nor expensive.
New pyrazolopyrimidines and pyrazoloquinazolines were synthesized through the uncatalyzed reaction of 5-amino-3-arylpyrazole-4-carbonitriles with aldehydes and 1,3-dicarbonyl compounds.
In DMSO solution, derivatives (III) exist in equilibrium of two tautomeric forms in various ratios depending on the nature of aryl substituents in chalcone building blocks.
4-Alkyl-3,4-dihydropyrimidin-2(1H)-ones possess a number of important properties in comparison with their 4-aryl analogues. We show that these compounds can be synthesised by a simple one-pot reaction of urea or thiourea, different aliphatic aldehydes (from acetaldehyde to valeraldehyde) and various dicarbonyl compounds (ethyl acetoacetate, pentane-2,4-dione, N-(4-chlorophenyl)-3-oxobutanamide, acetoacetaldehyde dimethylacetal) in refluxing DMF or HOAc without use of any catalyst. The methylation of 4-alkyl-5-C(O)R-3,4-dihydropyrimidin-2(1H)-ones leads to 1-methyl derivatives.
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