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BF 3 -Mediated Acetylation of Pyrazolo[1,5- a ]pyrimidines and Other π-Excedent ( N -Hetero)arenes

2022; American Chemical Society; Volume: 87; Issue: 15 Linguagem: Inglês

10.1021/acs.joc.2c00881

1520-6904

Sandra‐L. Aranzazu, Alexis Tigreros, Andres Arias-Gómez, Jhon Zapata‐Rivera, Jaime Portilla,

Synthesis of heterocyclic compounds

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.