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Synlett 2015; 26(12): 1744-1748
DOI: 10.1055/s-0034-1380751
DOI: 10.1055/s-0034-1380751
letter
Synthesis of 2-Quinolinones through Palladium(II) Acetate Catalyzed Cyclization of N-(2-Formylaryl)alkynamides
Weitere Informationen
Publikationsverlauf
Received: 26. März 2015
Accepted after revision: 20. April 2015
Publikationsdatum:
01. Juni 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201512/lookinside/thumbnails/st-2015-w0217-l_10-1055_s-0034-1380751-1.jpg)
Abstract
A Pd(OAc)2-catalyzed cyclization of N-(2-formylaryl)alkynamides initiated by the oxypalladation of alkynes was developed. The method provides a new approach for the efficient and atom-economical synthesis of 2-quinolinone derivatives.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380751.
- Supporting Information
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- 12 Synthesis of 2-Quinolinones; General Procedure: Pd(OAc)2 (5 mol%), 4,4′-(MeO)2bpy (10 mol%), and MS (20% w/w) were suspended in AcOH–DCE (1:2, 2 mL) and stirred at room temperature for 5 min under N2. Substrate 1 (0.2 mmol) was added and the mixture was stirred at 80 °C. The progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was purified by silica gel column chromatography to afford the corresponding product. 3-Acetylquinolin-2(1H)-one (2a) Yield: 31 mg (82%); white solid; 1H NMR (400 MHz, DMSO-d 6): δ = 12.09 (s, 1 H), 8.43 (s, 1 H), 7.85 (dd, J = 1.0, 7.8 Hz, 1 H), 7.62–7.58 (m, 1 H), 7.33 (d, J = 8.4 Hz, 1 H), 7.23–7.19 (m, 1 H), 2.61 (s, 3 H); 13C NMR (100 MHz, DMSO-d 6): δ = 197.8, 160.9, 143.5, 140.9, 133.3, 130.6, 129.8, 122.8, 118.5, 115.4, 31.1.
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For reviews, see:
For reviews on palladium-catalyzed formation of heterocyclic compounds, see:
For selected examples, see:
For recent reviews on biological studies of 2-quinolinones, see:
For recent selected examples on medicinal activities of 2-quinolinones, see:
For reviews, see:
For recent examples, see:
For examples of N-transacylation reactions of amides with carboxylic acids, see: