Citation: Yin Ke, Duan Zhengkang, Zhang Lei, Zhu Hongwen. Advance in the Application of Novel Cyanides in Synthesizing α-Aminonitriles through the Strecker Reaction[J]. Chemistry, ;2018, 81(3): 209-216. shu

Advance in the Application of Novel Cyanides in Synthesizing α-Aminonitriles through the Strecker Reaction

School of Chemical Engineering, Xiangtan University, Xiangtan 411105

Corresponding author: Duan Zhengkang, dzk0607@163.com
Received Date: 19 September 2017
Accepted Date: 21 November 2017

Figures(16)

α-Aminonitriles are significantly important intermediates for the syntheses of numerous amino acids. At present, α-aminonitriles have been widely used in chemistry, biology, medicine and other fields. As one of the most important methods for synthesizing α-aminonitriles, the Strecker reaction has been attracting the great attention of the researchers. However, the traditional Strecker reaction takes highly toxic HCN as cyanide source, it is dangerous and requires harsh operating conditions, which severely limits the development of this reaction. Therefore, to find a non-toxic and eco-friendly cyanide is the key to solve this problem. In this paper, the new cyanide species reported in the past decade are divided into TMSCN (trimethylsilyl cyanide), metal cyanides and organic cyanides. Then, the progress of these three cyanide compounds in the synthesis of α-aminonitrile by Strecker reaction is reviewed. Particularly, the catalyst development and catalytic mechanism of Strecker reaction with TMSCN as cyanide source are expounded. The application of some commonly used metal cyanides and organic cyanides in the Strecker reaction is also introduced. Moreover, the research trends of Strecker reaction are prospected.
- α-Aminonitriles,
- Strecker reaction,
- Novel cyanides
1. [1]
  R O Duthaler. Tetrahedron, 1994, 50(22):1539~1650.
2. [2]
  K S Indalkar, C K Khatri, G U Chaturbhuj. Tetrahed. Lett., 2017, 58(22):2144~2148.
3. [3]
  J Wang, X Liu, X Feng. Chem. Rev., 2011, 111(11):6947~83.
4. [4]
5. [5]
6. [6]
  J J Li. Name reation:a collection of detailed reaction mecharisms, 3rd ed. Heidelberg:Springer-Verlag, 2006.
7. [7]
  X H Cai, B Xie. Arkivoc, 2014, (1):205~248.
8. [8]
9. [9]
10. [10]
  P Li, Y Zhang, Z Chen et al. Tetrahed. Lett., 2017, 58(19):1854~1858.
11. [11]
  S S Mansoor, K Aswin, K Logaiya et al. J. Saudi Chem. Soc., 2016, 20(1):S202~S210.
12. [12]
  S M Vahdat, S Khaksar, M Khavarpour. Chin. Chem. Lett., 2011, 42(5):543~546.
13. [13]
  H Ghafuri, M Roshani. RSC Adv., 2014, 4(102):58280~58286.
14. [14]
  A Sengupta, C Su, C Bao et al. ChemCatChem, 2015, 6(9):2507~2511.
15. [15]
16. [16]
  M G Dekamin, Z Mokhtari. Cheminform, 2012, 68(3):922~930.
17. [17]
  A K Shah, N U H Khan, G Sethia et al. Appl. Catal. A, 2012, s419-420(420):22~30.
18. [18]
  Pamar, M Geetagovender, P Pillay et al. Ind. J. Chem., 2015, 54:110~116.
19. [19]
  A Teimouri, L Ghorbanian, A Moatari. Bull. Chem. Soc. Ethiopia, 2014, 28(3):441.
20. [20]
21. [21]
  M G Dekamin, M Azimoshan, L Ramezani. Green Chem., 2013, 44(27):811~820.
22. [22]
  A Maleki, R F Haji, M Ghassemi et al. J. Chem. Sci., 2017, 129(4):1~6.
23. [23]
  B Nammalwar, C Fortenberry, R A Bunce. Tetrahed. Lett., 2014, 55(2):379~381.
24. [24]
  S S Reddy, B R P Reddy, P V G Reddy. Chin. Chem. Lett., 2015, 26(6):739~743.
25. [25]
  Y Pérez-Fuertes, J E Taylor, D A Tickell et al. J. Org. Chem., 2011, 76(15):6038~6047.
26. [26]
  T Ooi, Y Uematsu, K Maruoka. J. Am. Chem. Soc., 2006, 37(25):2548~2549.
27. [27]
  S J Zuend, M P Coughlin, M P Lalonde et al. Nature, 2009, 461(7266):968~970.
28. [28]
29. [29]
  H S Wang, L F Zhao, Z M Du. Chin. J. Chem., 2006, 37(1):135~137.
30. [30]
  S Shah, B Singh. Cheminform, 2012, 53(2):151~156.
31. [31]
  Z Li, Y H Ma, J Xu et al. Cheminform, 2010, 51(30):3922~3926.
32. [32]
  X Hu, Y Ma, Z Li. J. Organomet. Chem., 2012, 43(34):70~74.
33. [33]
  P Kaur, S Pindi, W Wever et al. J. Org. Chem., 2010, 41(49):5144~5150.
34. [34]
  A S Paraskar, A Sudalai. Cheminform, 2006, 47(32):5759~5762.
35. [35]
  T Sakai, T Soeta, K Endo et al. Org. Lett., 2013, 44(35):2422~2425.
36. [36]
  S Saravanan, A Sadhukhan, N U Khan et al. J. Org. Chem., 2012, 77(9):4375~4384.
37. [37]
38. [38]
  F Cruz-Acosta, A Santos-Exposito, P D Armas et al. Chem. Commun., 2010, 41(12):6839~6841.
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