Abstract
New green one-pot four-component reactions of thiourea, malononitrile halohydrocarbon, aldehydes and alkyl halide have been successfully developed in eco-friendly water solvent through available phase-transfer catalyst, to access high yields of 2-amino-3-cyano-4-aryl-6-sulfanepyrimidines.
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References
A. Domling, W. Wang, K. Wang, Chem. Rev. 112, 3083–3135 (2012)
W. M. Nau, G. Ghale, A. Henning, H. Bakirci, D. M. Bailey, J. Am. Chem. Soc. 131, 11558–11570 (2009)
Z. Chen, A. M. Venkatesan, C. M. Dehnhardt, S. Ayral-Kaloustian, N. Brooijmans, R. Mallon, L. Feldberg, I. Hollander, J. Lucas, Y. Ker, F. Kong, T. S. Mansour, J. Med. Chem. 53, 3169–3182 (2010)
D. H. Slee, Y. Chen, X. Zhang, M. Moorjani, M. C. Lanier, E. Lin, J. K. Rueter, J. P. Williams, S. M. Lechner, S. Markison, S. Malany, M. Santos, R. S. Gross, K. Jalali,Y. Sai, Z. Zuo, C. Yang, J. C. Castro-Palomino, M. I. Crespo, M. Prat, S. Gual, J-L Díaz, and J. Saunders, J. Med. Chem, 2008, 51, 1719–1729
K. Danel, E. B. Pedersen, C. Nielsen, J. Med. Chem. 41, 191–198 (1998)
A. Kamal, J. S. Reddy, M. J. Ramaiah, E. V. Bharathi, D. Dastagiri, M. Kashi Reddy, Bopprganic Med. Chem. Lett., 2010, 20, 5232–5236
T. Tan, M. Wang, N. Chen, Chinese J. Chem., 2012, 386–390
Z. Wang, Y. Wang, W. -X. Zhang, Z. Hou, Z. Xi, J. Am. Chem. Soc. 131, 15108–15109 (2009)
M. Movassaghi, M. D. Hill, J. Am. Chem. Soc. 128, 14254–14255 (2008)
S. Majumder, A. L. Odom, Tetrahedron 66, 3152–3158 (2010)
M. Wende and J. A. Gladysz, J. Am. Chem. Soc. 2003, 125, 5861-5872
A. C. Donovan, J. F. Valliant, J. Am. Chem. Soc. 74, 8133–8138 (2009)
L. Rong, S. Xia, S. Yin et al., Res. Chem. Intermed. 39, 3699–3707 (2013)
S. Crestina, Consorti, Markus Jurisch (Organic Letter, John A. Gladysz, 2007), pp. 2309–2312
I. Komoto, S. Kobayashi, J. Org. Chem., 2004, 680–88
S. Wang, C. Guo, K. Cui, Y. Zhu, J. Ding, Xingyue, Zou, Y. Li, Ultrasonics Sonochemistry, 2015, 81–86
S. Rostamizadeh, M. Nojavan, J. Heterocycl. Chem. 51, 418–422 (2014)
T. Wang, S. Liu, C. H. Zheng, and H. W. He, J. Chem. Res., 2008, 11, 619–621
Acknowledgments
Financial support from National Natural Science Foundation of China (No. 21262018, 20862007), the Natural Science Foundation of Jiangxi Province in China (No. 2010GZH0070), and the Science and Technology Project of the Education Department of Jiangxi Province (No. GJJ13213).
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Xu, L., Gu, C., Li, R. et al. A green four-component synthesis of 2-amino-3-cyano-4-aryl-6-sulfanepyrimidine in water solvent using phase-transfer catalyst. J IRAN CHEM SOC 13, 597–604 (2016). https://doi.org/10.1007/s13738-015-0770-1
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DOI: https://doi.org/10.1007/s13738-015-0770-1