Citation: Mohsen Ameri, Alireza Asghari, Ali Amoozadeh, Hassan Daneshinejad, Davood Nematollahi. Electrosynthesis of hydroquinonethioethers using electrochemical oxidation of hydroquinone in the presence of thiouracil derivatives[J]. Chinese Chemical Letters, ;2014, 25(05): 797-801. doi: 10.1016/j.cclet.2014.03.016 shu

Electrosynthesis of hydroquinonethioethers using electrochemical oxidation of hydroquinone in the presence of thiouracil derivatives

1.
a Department of Chemistry, Semnan University, Semnan 35195-363, Iran;
2.
b College of Chemistry, Shahrood University of Technology, Shahrood 36155-316, Iran;
3.
c Faculty of Chemistry, Bu-Ali Sina University, Hamedan 65178-38683, Iran

Corresponding author: Alireza Asghari,
Received Date: 30 September 2013
Available Online: 19 February 2014

Electrochemical oxidation of hydroquinone (1a) has been studied in the presence of 6-methyl-2- thiouracil (3a) and 6-propyl-2-thiouracil (3b) as nucleophiles in a DMF/buffer mixture, using cyclic voltammetry and controlled-potential coulometry. The results indicated that the p-quinone (2a) derived from 1a participates in a 1,4-Michael addition reaction with the thiouracil derivatives (3a-b) to form the corresponding hydroquinonethioether derivatives (6a-6b). The electrosynthesis of these compounds (6a-b) has been successfully performed on carbon rod electrodes in an undivided cell in good yield and purity.
- Electrochemical oxidation,
- Cyclic voltammetry,
- Thiouracil derivatives,
- 1,4-Michael addition,
- Hydroquinonethioether
1. [1]
  [1] M.A. Ghanem, Electrocatalytic activity and simultaneous determination of catechol and hydroquinone at mesoporous platinum electrode, Electrochem. Commun. 9 (2007) 2501-2506.
2. [2]
  [2] N.Q. Ran, D.R. Knop, K.M. Draths, J.W. Frost, Benzene-free synthesis of hydroquinone, J. Am. Chem. Soc. 123 (2001) 10927-10934.
3. [3]
  [3] S.J. Li, Y. Xing, G.F.Wang,A graphene-based electrochemical sensor for sensitive and selective determination of hydroquinone, Microchim. Acta 176 (2012) 163-168.
4. [4]
  [4] S.S.H. Davarani, A.R. Fakhari, A. Shaabani, et al., A facile electrochemical method for the synthesis of phenazine derivatives via an ECECC pathway, Tetrahedron Lett. 49 (2008) 5622-5624.
5. [5]
  [5] D. Nematollahi, B. Dadpou, Electrochemical pyridination of hydroquinone in aqueous solution, Monatsh. Chem. 142 (2011) 1235-1239.
6. [6]
  [6] D. Nematollahi, A. Amani, E. Tammari, Electrosynthesis of symmetric and highly conjugated benzofuran via a unique ECECCC electrochemical mechanism: evidence for predominance of electrochemical oxidation versus intramolecular cyclization, J. Org. Chem. 72 (2007) 3646-3651.
7. [7]
  [7] A.R. Fakhari, H. Ahmara, S.S.H. Davarania, et al., Electro-organic synthesis of 2- amino-3-cyano-benzofuran derivatives using hydroquinonesandmalononitrile, Synth. Commun. 41 (2011) 561-568.
8. [8]
  [8] S.S.H. Davarania, D. Nematollahi, M. Shamsipur, et al., Electrochemical oxidation of 2,3-dimethybydroquinone in the presence of 1,3-dicarbonyl compounds, J. Org. Chem. 71 (2006) 2139-2142.
9. [9]
  [9] S. Shahrokhian, A. Hamzehloei, Electrochemical oxidation of catechol in the presence of 2-thiouracil: application to electro-organic synthesis? Electrochem. Commun. 5 (2003) 706-710.
10. [10]
  [10] D. Nematollahi, V. Hedayatfar, Diversity in electrochemical oxidation of dihydroxybenzenes in the presence of 1-methylindole, J. Chem. Sci. 123 (2011) 709- 717.
11. [11]
  [11] M.D. Ryan, A. Yueh, W.Y. Chen, The electrochemical oxidation of substituted catechols, J. Electrochem. Soc. 127 (1980) 1489-1495.
12. [12]
  [12] A.J. Bard, Electrochemical Methods, 2nd ed., Wiley, New York, 2001, pp. 103-497.
13. [13]
  [13] S.S.H. Davarani, F.N. Sheijooni, N.H. Arvin, F. Moradi, Electrochemical synthesis of 6-amino-5-(3,4-dihydroxyphenyl) pyrimidine, Tetrahedron Lett. 49 (2008) 710- 714.
14. [14]
  [14] S.S.H. Davarani, D. Nematollahi, M. Shamsipur, An efficient electrochemical method for synthesis of (1H-1,2,4-triazol-3-ylthio)benzen-1,2-diol derivatives, Heteroat. Chem. 18 (2007) 644-649.
15. [15]
  [15] L. Fotouhi, S. Taghavi, D. Nematollahi, M.M. Heravi, Study of the oxidation of some catechols in the presence of 4-amino-3-thio-1,2,4-triazole by digital simulation of cyclic voltammograms, Int. J. Chem. Kinet. 39 (2007) 340-345.
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1.
沈阳化工大学材料科学与工程学院沈阳 110142