Synthesis 2016; 48(12): 1920-1926
DOI: 10.1055/s-0035-1561950
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Aerobic Oxidative Cyclization of Ketoxime Acetates with Pyridines for the Synthesis of Imidazo[1,2-a]pyridines

Zhi-Hui Ren*
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China   eMail: guanzhh@nwu.edu.cn
,
Mi-Na Zhao
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China   eMail: guanzhh@nwu.edu.cn
,
Yukun Yi
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China   eMail: guanzhh@nwu.edu.cn
,
Yao-Yu Wang
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China   eMail: guanzhh@nwu.edu.cn
,
Zheng-Hui Guan*
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China   eMail: guanzhh@nwu.edu.cn
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 24. Januar 2016

Accepted after revision: 23. Februar 2016

Publikationsdatum:
29. März 2016 (online)


Abstract

A copper(I)-catalyzed aerobic oxidative coupling of ketoxime acetates with simple pyridines for the synthesis of imidazo[1,2-a]pyridines has been developed. This reaction tolerates a wide range of functional groups and it affords a series of valuable imidazo[1,2-a]pyridines in high yields under mild conditions.

Supporting Information

 
  • References

    • 1a Sukhorukov AY, Ioffe SL. Chem. Rev. 2011; 111: 5004
    • 1b Vanos CM, Lambert TH. Chem. Sci. 2010; 1: 705
    • 2a Zhang J, Dong C, Du C, Luo G. Org. Process Res. Dev. 2015; 19: 352
    • 2b Huang K, Li S, Chang M, Zhang X. Org. Lett. 2013; 15: 484
    • 3a Seechurn CC. C. J, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
    • 3b Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722
    • 3c Wu X.-F, Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
  • 4 Zaman S, Mitsuru K, Abell AD. Org. Lett. 2005; 7: 609
  • 5 Gerfaud T, Neuville L, Zhu J. Angew. Chem. Int. Ed. 2009; 48: 572
  • 6 Tan Y, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 3676
  • 7 Faulkner A, Bower JF. Angew. Chem. Int. Ed. 2012; 51: 1675
    • 8a Ran L, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Green Chem. 2014; 16: 112
    • 8b Du W, Zhao M.-N, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Chem. Commun. 2014; 50: 7437
    • 8c Zhao M.-N, Hui R.-R, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Org. Lett. 2014; 16: 3082
    • 8d Liang H, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Chem. Eur. J. 2013; 19: 9789
    • 8e Ran L, Liang H, Guan Z.-H. Youji Huaxue 2013; 33: 66
    • 8f Zhao M.-N, Liang H, Ren Z.-H, Guan Z.-H. Synthesis 2012; 44: 1501
    • 8g Ren Z.-H, Zhang Z.-Y, Yang B.-Q, Wang Y.-Y, Guan Z.-H. Org. Lett. 2011; 13: 5394
    • 8h Guan Z.-H, Zhang Z.-Y, Ren Z.-H, Wang Y.-Y, Zhang X. J. Org. Chem. 2011; 76: 339
    • 9a Liu S, Liebeskind LS. J. Am. Chem. Soc. 2008; 130: 6918
    • 9b Huang H, Ji X, Wu W, Jiang H. Chem. Soc. Rev. 2015; 44: 1155
    • 9c Tang X, Huang L, Xu Y, Yang J, Wu W, Jiang H. Angew. Chem. Int. Ed. 2014; 53: 4205
    • 9d Ke J, Tang Y, Yi H, Li Y, Cheng Y, Liu C, Lei A. Angew. Chem. Int. Ed. 2015; 54: 6604
    • 9e Wei Y, Yoshikai N. J. Am. Chem. Soc. 2013; 135: 3756
  • 10 Chernyak N, Gevorgyan V. Angew. Chem. Int. Ed. 2010; 49: 2743
    • 11a Gueiffier A, Mavel S, Lhassani M, Elhakmaoui A, Snoeck R, Andrei G, Chavignon O, Teulade J.-C, Witvrouw M, Balzarini J, De Clercq E, Chapat J.-P. J. Med. Chem. 1998; 41: 5108
    • 11b Hand ES, Paudler WW. J. Org. Chem. 1978; 43: 2900
    • 12a Cai Z.-J, Wang S.-Y, Ji S.-J. Adv. Synth. Catal. 2013; 355: 2686
    • 12b Mohan DC, Donthiri RR, Rao SN, Adimurthy S. Adv. Synth. Catal. 2013; 355: 2217
    • 12c Bagdi AK, Rahman M, Santra S, Majee A, Hajra A. Adv. Synth. Catal. 2013; 355: 1741
    • 12d Zhang Y, Chen Z, Wu W, Zhang Y, Su W. J. Org. Chem. 2013; 78: 12494
    • 12e Huang H, Ji X, Tang X, Zhang M, Li X, Jiang H. Org. Lett. 2013; 15: 6254