SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 3: 672 - 675

DOI: https://doi.org/10.6023/cjoc201412033

ARTICLE

Construction of Methylenebisamides in Aqueous Phase Using N,N-Dimethylacetamide to Provide Methylene

  • Chen Jie ,
  • Mao Jincheng ,
  • Zheng Yang
Expand
  • a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123;
    b State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, Southwest Petroleum University, Chengdu 610500

Received date: 2014-12-19

  Revised date: 2015-01-16

  Online published: 2015-01-28

Supported by

Project supported by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry, the Priority Academic Program Development of Jiangsu Higher Education Institutions, and the Key Laboratory of Organic Synthesis of Jiangsu Province.

Fold

Abstract

A variety of bisamides which are key fragments in the formation of peptidomimetic compounds were synthesized. An effective method to synthesize methylenebisamides is by the reaction of amides with N,N-dimethylacetamide (DMAC) using Na2S2O8 as the oxidant and (NH4)2Ce(NO3)6 as the catalyst in water. The structures of product were confirmed by 1H NMR, 13C NMR and LRMS. The methodology will provide new strategies for the synthesis of methylenebisamides, which has the advantage of environment-friendly, simple workup and high yield.

Key words： amides; methylenebisamides; water

Cite this article

Chen Jie , Mao Jincheng , Zheng Yang . Construction of Methylenebisamides in Aqueous Phase Using N,N-Dimethylacetamide to Provide Methylene[J]. Chinese Journal of Organic Chemistry, 2015 , 35(3) : 672 -675 . DOI: 10.6023/cjoc201412033

References

[1] Alemán, C.; Puiggali, J. J. Org. Chem. 1995, 60, 910.
[2] Pallai, P. V.; Struthers, R. S.; Goodman, M.; Moroder, L.; Wunsch, E.; Vale, W. Biochemistry. 1985, 24, 1933.
[3] Rodriguez, M.; Dubreuil, P.; Bali, J.-P.; Martinez, J. J. Med. Chem. 1987, 30, 758.
[4] Kamogawa, H.; Minoura, S.; Miyama, S. J. Polym. Sci., Polym. Chem. 1990, 28, 1435.
[5] Fernández, A. H.; Alvarez, R. M.; Abajo, T. M. Synthesis 1996, 1299.
[6] Gilbert, E. E. Synthesis 1972, 30.
[7] Magat, E. E.; Faris, B. F.; Reith, J. E.; Salisbury, L. F. J. Am. Chem. Soc. 1951, 73, 1028.
[8] Wang, Q.; Sun, L.; Jiang, Y.; Li, C. Beilstein J. Org. Chem. 2008, 4, 51.
[9] Pan, L.; Huang, L.; Xie, C. Lett. Org. Chem. 2013, 10, 770.
[10] Zhang, L.; Peng, C. Zhao, D.; Wang, Y.; Fu, H.-J.; Shen, Q.; Li, J.-X. Chem. Commun. 2012, 48, 5928.
[11] Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176.
[12] Li, Y.; Xue, D.; Lu, W.; Wang, C.; Liu, Z.-T.; Xiao, J. Org. Lett. 2014, 16, 66.
[13] Chill, S. T.; Mebane, R. C. Synth. Commun. 2010, 40, 2014.
[14] Ohashi, Y.; Terao, Y.; Sekiya, M. Chem. Pharm. Bull. 1978, 26, 653.
[15] Tanimoto, S.; Horikawa, J.; Oda, R. J. Synth. Org. Chem., Jpn. 1969, 27, 59.

Options
Outlines

/

〈 〉