Pyrazolo[1,5-a]pyrimidine (PP) derivatives are an enormous family of N-heterocyclic compounds that possess a high impact in medicinal chemistry and have attracted a great deal of attention in material science recently due to their significant photophysical properties. Consequently, various researchers have developed different synthesis pathways for the preparation and post-functionalization of this functional scaffold. These transformations improve the structural diversity and allow a synergic effect between new synthetic routes and the possible applications of these compounds. This contribution focuses on an overview of the current advances (2015–2021) in the synthesis and functionalization of diverse pyrazolo[1,5-a]pyrimidines. Moreover, the discussion highlights their anticancer potential and enzymatic inhibitory activity, which hopefully could lead to new rational and efficient designs of drugs bearing the pyrazolo[1,5-a]pyrimidine core.
An operably simple microwave-assisted BF3-mediated
acetylation
reaction of pyrazolo[1,5-a]pyrimidines and a plausible
mechanism based on density functional theory (DFT) theoretical calculations
for this transformation are reported. Remarkably, and to the best
of our knowledge, this is the first example of the direct acetylation
for the functional pyrazolo[1,5-a]pyrimidine (PP)
core. The synthesis of this essential building block is reported in
high yields using mild reaction conditions, inexpensive reagents,
and even substrates with electron-deficient or highly hindered groups.
In addition, one of the new methyl ketones was successfully used as
a substrate for producing novel and valuable bis-electrophilic compounds
with yields of up to 90%. Notably, the discovered acetylation method
was successfully applied in other π-excedent (N-hetero)aromatic substrates.
NaF/Al2O3 and SiO2-mediated solvent-free syntheses of Reversan and similar compounds, first cyclizing chalcones with 5-aminopyrazoles under fusion heating and then by the direct amidation reaction of esters under microwaves conditions, are reported.
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