BF3‑Mediated Acetylation of Pyrazolo[1,5‑a]pyrimidines and Other π‑Excedent (N‑Hetero)arenes

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 ex...

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Veröffentlicht in:Journal of organic chemistry 2022-08, Vol.87 (15), p.9839-9850
Hauptverfasser: Aranzazu, Sandra-L., Tigreros, Alexis, Arias-Gómez, Andres, Zapata-Rivera, Jhon, Portilla, Jaime
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00881