Ultrasound Assisted α‐Arylation of Ketones: A Rapid Access to Isoquinolinone Derivatives
In the current study we have demonstrated the effectiveness of ultrasound, a source of green energy, in accessing various isoquinolin‐1(2H)‐one derivatives via the sequential two‐step reaction in a single pot. The methodology involved ultrasound assisted Cu‐catalyzed α‐arylation of ketones with 2‐io...
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Veröffentlicht in: | ChemistrySelect (Weinheim) 2022-10, Vol.7 (40), p.n/a |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | In the current study we have demonstrated the effectiveness of ultrasound, a source of green energy, in accessing various isoquinolin‐1(2H)‐one derivatives via the sequential two‐step reaction in a single pot. The methodology involved ultrasound assisted Cu‐catalyzed α‐arylation of ketones with 2‐iodobenzamide (via a C−C bond formation) followed by intramolecular cyclization (via the C−N bond formation) in the same pot. The role of ultrasound, catalyst, base and solvent in the current transformation was evaluated and the generality as well as scope of the methodology was examined via synthesizing a variety of compounds in acceptable to good (49–93 %) yields. The application potential of the methodology was demonstrated further via synthesizing a reported bioactive arylisoquinolinamine derivative of medicinal significance. Further, the encouraging inhibition of TNF‐α in vitro (>50 % at 10 μM) was shown by some of the synthesized compounds e. g. 3 j, 3 m and 3 p.
The construction of isoquinolin‐1(2H)‐one ring via the first usage of ultrasound in α‐arylation of ketones is described. |
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ISSN: | 2365-6549 2365-6549 |
DOI: | 10.1002/slct.202202710 |