RSC Advances
Paper
4 D. Kumar, N. M. Kumar, K. H. Chang, R. Gupta and K. Shah,
Bioorg. Med. Chem. Lett., 2011, 21, 5897–5900.
5 L. M. T. Frija, A. J. L. Pombeiro and M. N. Kopylovich, Eur. J.
Org. Chem., 2017, 2017, 2670–2682.
6 O. A. Attanasi, S. Berretta, L. D. Crescentini, G. Favi,
P. Filippone, G. Giorgi, S. Lillini and F. Mantellini,
Tetrahedron Lett., 2007, 48, 2449–2451.
Reaction mechanism
A plausible pathway was outlined in Scheme 5. The [DBUH]+
made the cyanide activated, the S2À with the nitrile to yield
intermediate A. Finally, the nal product thioamides are ob-
tained from the intermediate A.
7 A. S. Gurjar, V. Andrisano, A. D. Simone and V. S. Velingkar,
Bioorg. Chem., 2014, 57, 90–98.
Conclusion
8 G. L. Perlovich, A. N. Proshin, T. V. Volkova, L. N. Petrova and
S. O. Bachurin, Mol. Pharmaceutics, 2012, 9, 2156–2167.
9 A. S. Mayhoub, L. Marler, T. P. Kondratyuk, E. J. Park,
J. M. Pezzuto and M. Cushman, Bioorg. Med. Chem., 2012,
20, 510–520.
10 Y. Sun, W. Wu and H. Jiang, Eur. J. Org. Chem., 2014, 2014,
4239–4243.
11 H. Xu, H. Deng, Z. Li, H. Xiang and X. Zhou, Eur. J. Org.
Chem., 2013, 7054–7057.
In summary, we have developed an efficient [DBUH][OAc]-
promoted the reaction of different aryl nitriles with Na2S$9H2-
O as an inexpensive, conveniently available and easy-to-handle
sulde surrogate under solvent-free conditions at room
temperature. The generated products were easily separated
from the ILs which could be reclaimed at least ve times. The
operational environmental friendliness and simplicity of this
method highlights its potential application in organic synthesis
and pharmaceutical industry.
12 K. A. Mahammed, V. P. Jayashankar, N. Premsai Rai,
K. Mohana Raju and P. N. Arunachalam, Synlett, 2009, 14,
2338–2340.
Experimental
13 M. L. Boys and V. L. Downs, Synth. Commun., 2006, 36, 295–
298.
14 T. Kanbara, K. Okamoto and T. Yamamoto, Synlett, 2007,
2007, 2687–2690.
15 C. K. Khatri, A. S. Mali and G. U. Chaturbhuj, Monatsh.
Chem., 2017, 148, 1463–1468.
General procedure for preparation of ionic liquid [DBUH][OAc]:
to a 250 mL three-necked ask was added 40 mmol of DBU.
Acetic acid (40 mmol) was then added slowly dropwise in ice
bath. Aer dropwise addition, the ice bath was removed and the
reaction mixture was stirred at room temperature for 24 h. The
ꢀ
oil residue was dried in vacuo at 60 C for 24 h to afford [DBU]
16 A. Manaka and M. Sato, Synth. Commun., 2005, 35, 761–764.
17 S. Ray, A. Bhaumik, A. Dutta, R. J. Butcher and
C. Mukhopadhyay, Tetrahedron Lett., 2013, 54, 2164–2170.
18 Z. Yin and B. Zheng, J. Sulfur Chem., 2013, 34, 527–531.
[OAc] as a light yellow, viscous liquid. The characteristic data is
accord with the literature.36
The general procedure of preparing all products is similar.
Taking the model reaction as an example: benzonitrile 1a (1
mmol) and [DBUH][OAc] (3 mmol) were added into a 10 mL
bottle. Aer 2.0 h, by adding about 4 mL H2O aer the reaction
to disperse the solid product, the reaction mixture was extracted
with ethyl acetate (3 Â 4 mL) followed by H2O (5 mL), and the
mixture was puried by column chromatography.
´
´
¨
´
´
19 Z. Kaleta, G. Tarkanyi, A. Gormory, F. Kalman, T. Nagy and
´
T. Soos, Org. Lett., 2006, 8, 1093–1095.
20 U. Pathak, L. Pandey, S. Mathur and M. Suryanarayana,
Synthesis, 2011, 44, 377–379.
21 C.-H. Yang, G.-J. Li, C.-J. Gong and Y.-M. Li, Tetrahedron,
2015, 71, 637–642.
22 T. J. Curphe, J. Org. Chem., 2002, 67, 6461–6473.
23 J. Bergman, B. Pettersson, V. Hasimbegovic and
P. H. Svensson, J. Org. Chem., 2011, 76, 1546–1553.
24 D. Cho, J. Ahn, K. A. De Castro, H. Ahn and H. Rhee,
Tetrahedron, 2010, 66, 5583–5588.
Conflicts of interest
There are no conicts to declare.
Acknowledgements
25 L. Doszczak and J. Rachon, Chem. Commun., 2000, 2093–
2094.
We are grateful to the Major scientic and technological inno-
vation projects of Hangzhou City (No. 20162011A036) and the 26 S. Goswami, A. C. Maity and N. K. Das, J. Sulfur Chem., 2007,
Program for Changjiang Scholars and Innovative Research
28, 233–237.
Team in Chinese University (IRT 1231) for providing nancial 27 B. Kaboudin and D. Elhamifar, Synthesis, 2006, 224–226.
support.
28 B. Kaboudin and L. Malekzadeh, Synlett, 2011, 2011, 2807–
2810.
29 B. Kaboudin, V. Yarahmadi, J.-y. Kato and T. Yokomatsu,
RSC Adv., 2013, 3, 6435.
References
1 F. Wang, R. Langley, G. Gulten, L. G. Dover, G. S. Besra, 30 H. R. Lagiakos, A. Walker, M.-I. Aguilar and P. Perlmutter,
W. R. Jacobs Jr and J. C. Sacchettini, J. Exp. Med., 2007,
204, 73–78.
2 T. S. Jagodzinski, Chem. Rev., 2003, 103, 197–228.
Tetrahedron Lett., 2011, 52, 5131–5132.
31 A. K. Yadav, V. P. Srivastava and L. D. S. Yadav, Synth.
Commun., 2013, 44, 408–416.
3 P. Wipf and S. A. Venkatraman, J. Org. Chem., 1996, 61, 8004– 32 W. Lu, J. Ma, J. Hu, J. Song, Z. Zhang, G. Yang and B. Han,
8005.
Green Chem., 2014, 16, 221–225.
174 | RSC Adv., 2018, 8, 170–175
This journal is © The Royal Society of Chemistry 2018