Synlett 2017; 28(13): 1581-1585
DOI: 10.1055/s-0036-1588171
cluster
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Aerobic Oxidation and Oxygenation of Anilines and Acetaldehydes with Dioxygen for the Concise Synthesis of 2-Aroylquinolines

Ziyuan Li*
a  Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, No. 24 South Section 1, Yihuan Road, Chengdu 610065, P. R. of China   eMail: liziyuan@scu.edu.cn
b  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   eMail: jiaoning@pku.edu.cn
,
Xiaoyang Wang
b  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   eMail: jiaoning@pku.edu.cn
,
Lifang Ma
a  Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, No. 24 South Section 1, Yihuan Road, Chengdu 610065, P. R. of China   eMail: liziyuan@scu.edu.cn
,
Ning Jiao*
b  State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China   eMail: jiaoning@pku.edu.cn
› Institutsangaben
Gefördert durch: National Basic Research Program of China (Grant / Award Number: '2015CB856600')
Gefördert durch: Peking University Health Science Center (Grant / Award Number: 'BMU20160541')
Gefördert durch: National Young Top-Notch Talent Support Program
Gefördert durch: Fundamental Research Funds for the Central Universities (Grant / Award Number: '2016SCU11020')
Gefördert durch: National Natural Science Foundation of China (Grant / Award Number: '21325206', '21632001')
Weitere Informationen

Publikationsverlauf

Received: 28. Januar 2017

Accepted after revision: 15. März 2017

Publikationsdatum:
19. April 2017 (online)


Abstract

A concise and efficient aerobic oxidation and oxygenation approach for the construction of 2-aroylquinolines has been developed through copper-catalyzed annulation of anilines, acetaldehydes, and dioxygen. 2,2,6,6-Tetramethylpiperidine-1-oxyl was employed to direct the selectivity toward the desired 2-aroyl products. Molecular oxygen was used in this transformation as an environmentally benign source of oxygen.

Supporting Information

 
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  • 15 Phenyl(3-phenylquinolin-2-yl)methanone (9a); Typical Procedure To a reaction tube charged with CuNO3·3 H2O (12.1 mg, 0.05 mmol, 20 mol%) and TEMPO (78.1 mg, 0.5 mmol, 2 equiv) under O2 (1 atm) was added a solution of aniline (2a, 0.25 mmol, 1 equiv), phenylacetaldehyde (3a, 1 mmol, 4 equiv), and H2O (135 μL, 7.5 mmol, 30 equiv) in DMF (3 mL). The mixture was stirred at 100 °C for 12 h then cooled to r.t. The mixture was diluted with EtOAc, washed with sat. aq NaHCO3, water, and brine, dried (Na2SO4), and concentrated in vacuo to give dark residue that was purified by flash chromatography [silica gel, PE–EtOAc (50:1 to 30:1)] to give an off-white oil; yield: 55 mg (71%). 1H NMR (400 MHz, CDCl3): δ = 8.28 (s, 1 H), 8.19 (d, J = 8.4 Hz, 1 H), 7.86–7.94 (m, 3 H), 7.76–7.80 (m, 1 H), 7.64–7.68 (m, 1 H), 7.52–7.56 (m, 1 H), 7.38–7.41 (m, 4 H), 7.30–7.33 (m, 3 H). 13C NMR (100 MHz, CDCl3): δ = 195.1, 156.3, 146.1, 137.7, 137.2, 136.2, 134.1, 133.5, 130.5, 130.1, 129.7, 129.0, 128.6, 128.4, 128.1, 128.0, 127.9, 127.8. HRMS (ESI): m/z [M + H]+ calcd for C22H16NO: 310.1232; found: 310.1226.