Citation: Meng Tuanjie, Feng Cuilan, Liu Lantao, Wang Tao, Xu Kai, Zhao Wenxian. Palladium Catalyzed Oxidation of Ynamides Using Dimethyl Sulfoxide as Oxidant: A Facile Way to Synthesize α-Ketoamide Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(6): 1382-1388. doi: 10.6023/cjoc201601003 shu

Palladium Catalyzed Oxidation of Ynamides Using Dimethyl Sulfoxide as Oxidant: A Facile Way to Synthesize α-Ketoamide Derivatives

1.
Engineering Laboratory of Henan Province for Green Synthesis of Medicine, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000

Corresponding author: Liu Lantao, liult05@iccas.ac.cn Zhao Wenxian, zhwx2595126@163.com
Received Date: 3 January 2016
Revised Date: 4 February 2016

Fund Project: the Science and Technology Key Project of Henan Province No. 142102210635and the Program for University Key Young Teachers of Henan Province No. 2015GGJS-126Project supported by the National Natural Science Foundation of China Nos. U1204204, 21172139, 21202095

Figures(2)

A series of α-ketoamide derivatives were obtained from the palladium catalyzed oxidation of ynamides using cheap and readily available dimethyl sulfoxide as oxidant and solvent under room temperature. The structures of all products were characterized by ¹H NMR, ¹³C NMR, IR and HRMS. This protocol has some distinct advantages of mild conditions, simple work-up, readily available starting materials and fast reaction rate.
- dimethyl sulfoxide,
- ynamides,
- α-ketoamides,
- synthesis,
- oxidation
1. [1]
  Kher, S. S.; Penzo, M.; Fulle, S.; Finn, P. W.; Blackman, M. J.; Jirgensons, A. Bioorg. Med. Chem. Lett. 2014, 24, 4486.
2. [2]
  Korukonda, R.; Guan, N.; Dalton, J. T.; Liu, J.; Donkor, I. O. J. Med. Chem. 2006, 49, 5282. (b) Donkor, I. O.; Han, J.; Zheng, X. J. Med. Chem. 2004, 47, 72. (c) Yoo, Y. J.; Nam, D. H.; Jung, S. Y.; Jang, J. W.; Kim, H. J.; Jin, C.; Pae, A. N.; Lee, Y. S. Bioorg. Med. Chem. Lett. 2011, 21, 2850. (d) Ovat, A.; Li, Z. Z.; Hampton, C. Y.; Asress, S. A.; Fernández, F. M.; Glass, J. D.; Powers, J. C. J. Med. Chem. 2010, 53, 6326.
3. [3]
  Mandadapu, S. R.; Weerawarna, P. M.; Gunnam, M. R.; Alliston, K. R.; Lushington, G. H.; Kim, Y.; Chang, K.-O.; Groutas, W. C. Bioorg. Med. Chem. Lett. 2012, 22, 4820.
4. [4]
  Steuer, C.; Gege, C.; Fischl, W.; Heinonen, K. H.; Bartenschlager, R.; Klein, C. D. Bioorg. Med. Chem. 2011, 19, 4067.
5. [5]
  Chen, J.-C.; Uang, B.-J.; Lyu, P.-C.; Chang, J.-Y.; Liu, K.-J.; Kuo, C.-C.; Hsieh, H.-P.; Wang, H.-C.; Cheng, C.-S.; Chang, Y.-H.; Chang, M. D.-T.; Chang, W.-S. W.; Lin, C.-C. J. Med. Chem. 2010, 53, 4545.
6. [6]
  Chiou, A.; Markidis, T.; Constantinou-Kokotou, V.; Verger, R.; KoKotos, G. Org. Lett. 2000, 2, 347.
7. [7]
  Bennett, F.; Huang, Y.; Hendrata, S.; Lovey, R.; Bogen, S. L.; Pan, W.; Guo, Z.; Prongay, A.; Chen, K. X.; Arasappan, A.; Venkatraman, S.; Velazquez, F.; Nair, L.; Sannigrahi, M.; Tong, X.; Pichardo, J.; Cheng, K.-C.; Girijavallabhan, V. M.; Saksena, A. K.; Njoroge, F. G. Bioorg. Med. Chem. Lett. 2010, 20, 2617.
8. [8]
  Lin, C.; Kwong, A. D.; Perni, R. B. Infect. Disord.: Drug Targets 2006, 6, 3.
9. [9]
  Schnopp, C.; Remling, R.; Möhrenschlager, M.; Weigl, L.; Ring, J.; Abeck, D. J. Am. Acad. Dermtol. 2002, 46, 73.
10. [10]
  Stella, S.; Chadha, A. Catal. Today 2012, 198, 345. (b) Singh, R. P.; Shreeve, J. M. J. Org. Chem. 2003, 68, 6063. (c) Guin, S.; Rout, S. K.; Gogoi, A.; Ali, W.; Patel, B. K. Adv. Synth. Catal. 2014, 356, 2559. (d) Zhang, X.; Yang, W.; Wang, L. Org. Biomol. Chem. 2013, 11, 3649. (e) Wang, H.; Guo, L.-N.; Duan, X.-H. Org. Biomol. Chem. 2013, 11, 4573.
11. [11]
12. [12]
13. [13]
  Dutta, S.; Kotha, S. S.; Sekar, G. RSC Adv. 2015, 5, 47265.
14. [14]
  Du, B.; Jin, B.; Sun, P. Org. Biomol. Chem. 2014, 12, 4586.
15. [15]
  Zhang, C.; Zong, X.; Zhang, L.; Jiao, N. Org. Lett. 2012, 14, 3280. (b) Mupparapu, N.; Khan, S.; Battula, S.; Kushwaha, M.; Gupta, A. P.; Ahmed, Q. N.; Vishwakarma, R. A. Org. Lett. 2014, 16, 1152.
16. [16]
  Zhang, C.; Xu, Z.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 11088.
17. [17]
18. [18]
  Xing, Q.; Shi, L.; Lang, R.; Xia, C.; Li, F. Chem. Commun. 2012, 48, 11023.
19. [19]
  Al-Rashid, Z. F.; Johnson, W. L.; Hsung, R. P.; Wei, Y.; Yao, P.-Y.; Liu, R.; Zhao, K. J. Org. Chem. 2008, 73, 8780.
20. [20]
  Huang, H.; He, G.; Zhu, X.; Jin, X.; Qiu, S.; Zhu, H. Eur. J. Org. Chem. 2014, 7174.
21. [21]
  Chikugo, T.; Yauchi, Y.; Ide, M.; Iwasawa, T. Tetrahedron 2014, 70, 3988.
22. [22]
  Xu, C.-F.; Xu, M.; Jia, Y.-X.; Li, C.-Y. Org. Lett. 2011, 13, 1556. (b) Wang, K.-B.; Ran, R.-Q.; Xiu, S.-D.; Li, C.-Y. Org. Lett. 2013, 15, 2374.
23. [23]
  Zuo, J.-F.; Huang, W.-S.; Li, L.; Xu, Z.; Zheng, Z.-J.; Yang, K.-F.; Xu, L.-W. RSC Adv. 2015, 5, 30389. (b) Liu, F.-L.; Chen, J.-R.; Zuo, Y.-Q.; Wei, Q.; Xiao, W.-J. Org. Lett. 2014, 16, 3768. (c) Le, H. V.; Ganem, B. Org. Lett. 2011, 13, 2584. (d) Vieira, A. A.; Azeredo, J. B.; Godoi, M.; Santi, C.; Júnior, E. N. S.; Braga, A. L. J. Org. Chem. 2015, 80, 2120. (e) Prasad, P. K.; Reddi, R. N.; Sudalai, A. Org. Lett. 2016, 18, 500.
24. [24]
  Gao, A.; Yang, F.; Li, J.; Wu, Y. Tetrahedron 2012, 68, 4950.
25. [25]
  Dekorver, K. A.; Hsung, R. P.; Song, W.-Z.; Wang, X.-N.; Walton, M. C. Org. Lett. 2012, 14, 3214. (b) Wang, X.-N.; Winston-Mcpherson, G. N.; Walton, M. C.; Zhang, Y.; Hsung, R. P.; Dekorver, K. A. J. Org. Chem. 2013, 78, 6233. (c) Dekorver, K. A.; Johnson, W. L.; Zhang, Y.; Hsung, R. P.; Dai, H.; Deng, J.; Lohse, A. G.; Zhang, Y.-S. J. Org. Chem. 2011, 76, 5092.
26. [26]
  Huang, H.; He, G.; Zhu, G.; Zhu, X.; Qiu, S.; Zhu, H. J. Org. Chem. 2015, 80, 3480. (b) Istrate, F. M.; Buzas, A. K.; Jurberg, I. D.; Odabachian, Y.; Gagosz, F. Org. Lett. 2008, 10, 925. (c) Lu, Z.; Cui, W.; Xia, S.; Bai, Y.; Luo, F.; Zhu, G. J. Org. Chem. 2012, 77, 9871. (d) Lu, Z.; Xu, X.; Yang, Z.; Kong, L.; Zhu, G. Tetrahedron Lett. 2012, 53, 3433. (e) Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763.
27. [27]
1. [1]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
2. [2]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
3. [3]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
4. [4]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
5. [5]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
6. [6]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
7. [7]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
8. [8]
  Peiyu Zhang , Aixin Song , Jingcheng Hao , Jiwei Cui . 高频超声法制备聚多巴胺薄膜综合实验. University Chemistry, 2025, 40(6): 210-214. doi: 10.12461/PKU.DXHX202407081
9. [9]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
10. [10]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
11. [11]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
12. [12]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
13. [13]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
14. [14]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 2309041-0. doi: 10.3866/PKU.WHXB202309041
15. [15]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
16. [16]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
17. [17]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
18. [18]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
19. [19]
  Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
20. [20]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(914)
HTML views(130)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142