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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1737 - 1744

DOI: https://doi.org/10.6023/cjoc202001020

Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source

  • Zhang Pengpeng ,
  • Han Shenghua ,
  • Chen Jianxin
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  • College of Chemistry and Material Science, Shanxi Normal University, Linfen, Shanxi 041004;
    College of Chemistry and Engineering, Shanxi Datong University, Datong, Shanxi 037009

Received date: 2019-11-14

  Revised date: 2020-03-04

  Online published: 2020-03-31

Supported by

Project supported by the Shanxi Provincal Foundation for Returnees Overseas Scientists (No. 0713), and the Natural Science Foundation of Shanxi Province (No. 2012011046-9).

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Abstract

The selective aminocarbonylation of vicinal diketones using carbamoylsilane as an amide source affords β-keto-α-siloxyamide derivatives in 62%~90% yields under mild conditions without using any oxidants and catalysts. The steric hindrance, which is both from the groups of vicinal diketones and the carbamoylsilanes, affects reaction selectivity on two carbonyl groups. The methoxymethyl or benzyl used as an amino protecting group, can be easily converted into hydrogen atom leading to β-keto-α-hydroxy secondary or primary amides. The simple procedure allows the preparation of various β-keto-α-hydroxy amide derivatives including primary, secondary and tertiary β-keto-α-hydroxy amide derivatives. The reaction has the advantages of mild conditions, less by-products, high selectivity, good yield and simple post-treatment, and it is a new method for the efficient preparation of β-keto-α-hydroxyamides.

Key words： carbamoylsilanes; β-keto-α-hydroxyamides; aminocarbonylation; nucleophilic addition; vicinal diketones

Cite this article

Zhang Pengpeng , Han Shenghua , Chen Jianxin . Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1737 -1744 . DOI: 10.6023/cjoc202001020

References

[1] Wellington, K. D.; Cambie, R. C.; Rutledge, P. S.; Bergquist, P. R. J. Nat. Prod. 2000, 63, 79.
[2] Park, J.-H.; Chang, J.-S.; El-Gamal, M. I.; Choi, W.-K.; Lee, W. S.; Chung, H. J.; Kim, H.-I.; Cho, Y.-J.; Lee, B.-S.; Jeon, H. R.; Lee, Y. S.; Choi, Y. W.; Lee, J.; Oh, C. H. Bioorg. Med. Chem. Lett. 2010, 20, 5895.
[3] Pritchard, d. R.; Wilden, J. D. Tetrahedron Lett. 2010, 51, 1819.
[4] Amada, H.; Matsuda, D.; Bohno, A. WO 2011034215, 2011[Chem. Abstr. 2011, 154, 385279].
[5] Yang, K.; Huang, J.; Eisele, F. WO 2013163889, 2013[Chem. Abstr. 2013, 159, 699243].
[6] Hu, X.; Xia, Q.; Zhao, Y.; Zheng, Q.; Liu, Q.; Chen, L.; Zhang, Q. Chem. Pharm. Bull. 2014, 62, 942.
[7] Mahiuddin, B.; Kimberly, A. G.; Hisashi, Y. J. Am. Chem. Soc. 2012, 134, 18566.
[8] Lv, X.-J.; Chen, Y.-H.; Liu, Y.-K. Org. Lett. 2019, 21, 190.
[9] Zhu, J.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1994, 35, 2787.
[10] Christoffers, J.; Werner, T.; Frey, W.; Baro, A. Chem.-Eur. J. 2004, 10, 1042.
[11] Wellington, K. D.; Cambie, R. C.; Rutledge, P. S.; Bergquist, P. R. J. Nat. Prod. 2000, 63, 79.
[12] Christoffers, J.; Baro, A.; Werner, T. Adv. Synth. Catal, 2004, 346, 143.
[13] Chooi, Y.; Hong, Y. J.; Cacho, R. A.; Tantillo, D. J.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 16805.
[14] Hayakawa, Y.; Kobayashi, T.; Izawa, M. J. Antibiot. 2013, 66, 731.
[15] Ding, G.-Z.; Liu, J.; Wang, J.-M.; Fang, I.; Yu, S.-S. J. Asian Nat. Prod. Res. 2013, 15, 446.
[16] Racv, L. D.; Frey, W.; Ivanov, I. C. Synlett 2004, 1584.
[17] Li, S.; Wang, S.-J. Heterocycl. Chem. 2008, 45, 1875.
[18] Wang, J.-W.; Yuan, Y.-C.; Xiong, R.; Zhang, D.; Du, Y.-F.; Zhao, K. Org. Lett. 2012, 14, 2210.
[19] Li, D.-M.; Schroder, K.; Bitterlich, B.; Tse, M. K.; Beller, M. Tetrahedron Lett. 2008, 49, 5976.
[20] Duschek, A.; Kirsch, S. F. Chem.-Eur. J. 2009, 15, 10713.
[21] Yu, J.; Cui, J.-A.; Zhang, C. Eur. J. Org. Chem. 2010, 7020.
[22] Takechi, S.; Kumagai, N.; Shibasaki, M. Tetrahedron Lett. 2011, 52, 2140.
[23] Asahara, H.; Nishiwaki, N. J. Org. Chem. 2014, 79, 11735.
[24] Miao, C.-B.; Wang, Y.-H.; Xing, M.-L.; Lu, X.-W.; Sun, X.-Q.; Yang, H.-T. J. Org. Chem. 2013, 78, 11584.
[25] Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. Org. React. 2003, 62, 1.
[26] Smith, A. M. R.; Billen, D.; Hii, K. K. Chem. Commun. 2009, 3925.
[27] Christoffers, J.; Werner, T.; Unger, S.; Frey, W. Eur. J. Org. Chem. 2003, 425.
[28] Baucherel, X.; Levoirier, E.; Uziel, J.; Juge, S. Tetrahedron Lett. 2000, 41, 1385.
[29] Zou, L.; Wang, B.; Mu, H.; Zhang, H.; Song, Y.; Qu, J. Org. Lett. 2013, 15, 3106.
[30] Nair, V.; Deepthi, A. Chem. Rev. 2007, 107, 1862.
[31] Wang, Y.-K.; Xiong, T.; Meng, Q. W. Tetrahedron 2015, 71, 85.
[32] Yu, S.-M.; Cui, K.; Lv, F.; Yang, Z.-Y.; Yao, Z.-J. Tetrahedron Lett. 2016, 57, 2818.
[33] Yao, Y.; Li, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2014, 34, 2124(in Chinese). (姚远, 李伟东, 陈建新, 有机化学, 2014, 34, 2124.)
[34] Yao, Y.; Li, W.-T.; Tong, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2015, 35, 223(in Chinese). (姚远, 李伟东, 仝文婷, 陈建新, 有机化学, 2015, 35, 223.)
[35] Chen, X.-J.; Chen, J.-X. Mendeleev Commun. 2013, 23, 106.
[36] Li, W.-D.; Han, S.-H.; Liu, Y.-H.; Chen, J.-X. Chin. J. Org. Chem. 2017, 37, 2423(in Chinese). (李伟东, 韩生华, 刘艳红, 陈建新, 有机化学, 2017, 37, 2423.)
[37] Zhang, W.-J.; Cao, P.; Guo, Q.-L.; Chen, J.-X. Curr. Org. Synth. 2017, 14, 1067.
[38] Ma, F.; Liu, H.; Chen, J.-X. Tetrahedron Lett. 2016, 57, 5246.
[39] Han, Y.-L.; Tong, W.-T.; Liu, H.; Chen, J.-X. Chin. J. Org. Chem. 2018, 38, 1993(in Chinese). (韩宇玲, 仝文婷, 刘慧, 陈建新, 有机化学, 2018, 38, 1993.)
[40] Tong, W.-T.; Cao, P.; Liu, Y.-H. Chen, J.-X. J. Org. Chem. 2017, 82, 11603.
[41] Cao, P.; Wen, X.-P.; Chen, J.-X. Synlett 2017, 28, 353.
[42] Ruan, L.; Shi, M.; Li, N.; Ding, X.; Yang, F.; Tang, J. Org. Lett. 2014, 16, 733.
[43] Cunico, R. F.; Chen, J.-X. Synth. Commun. 2003, 33, 1963.
[44] Reeves, J. T.; Lorenc, C.; Camara, K.; Li, Z.-B.; Lee, H. W.; Busacca, C. A.; Senanayake, C. H. J. Org. Chem. 2014, 79, 589.
[45] Schollkopt, U.; Beckhaus, H. Angew. Chem. Int. Ed. Engl. 1976, 15, 293.
[46] Davies, S. G.; Ichihara, O. Tetrahedron Lett. 1998, 39, 6045.
[47] Cunico, R. F.; Motta, A. R. Org. Lett. 2005, 7, 771.
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