Synthesis of 2-Quinolinones through Palladium(II) Acetate Catalyzed Cyclization of N-(2-Formylaryl)alkynamides

Jianbo Zhang; Xiuling Han; Xiyan Lu

doi:10.1055/s-0034-1380751

Synlett, Table of Contents

Synlett 2015; 26(12): 1744-1748
DOI: 10.1055/s-0034-1380751

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Synthesis of 2-Quinolinones through Palladium(II) Acetate Catalyzed Cyclization of N-(2-Formylaryl)alkynamides

Jianbo Zhang

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Email: xlhan@mail.sioc.ac.cn Email: xylu@mail.sioc.ac.cn

,

Xiuling Han*

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Email: xlhan@mail.sioc.ac.cn Email: xylu@mail.sioc.ac.cn

,

Xiyan Lu*

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Email: xlhan@mail.sioc.ac.cn Email: xylu@mail.sioc.ac.cn

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Abstract

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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.

Key words

cascade reaction - cyclization - oxypalladation - palladium - quinolinones

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References

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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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