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A Novel and Green Method for the Synthesis of Benzo-15-crown-5 Containing Sulphonylthiourea-Based Receptors
Corresponding Author(s) : Cong-Wen Ding
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
The nucleophilic reaction of 4'-aminobenzo-15-crown-5 and carbon disulphide in aqueous KOH afforded corresponding dithiocarbamate salt. Subsequent nucleophilic substitution reactions with sulfonamides aqueous NaOH provided benzo-15-crown-5-containing sulphonylthioureas. This novel, green method has the advantages of simple operation, high yields, easy product-isolation and environmental friendliness.
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- A.-F. Li, J.-H. Wang, F. Wang and Y.-B. Jiang, Chem. Soc. Rev., 39, 3729 (2010).
- S. Nishizawa, K. Shigemori and N. Teramae, Chem. Lett., 1185 (1999).
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- B. Wu, G.-G. Liu, M.-Q. Li, Y. Zhang, S.-Y. Zhang, J.-R. Qiu, X.-P. Xu, S.-J. Ji and X.-W. Wang, Chem. Commun., 3992 (2011).
- Z. Ning, C. Yuan, H. Tian, Y. Fu, L. Li, L. Sun and H. Ågren, J. Mater. Chem., 22, 6032 (2012).
- M.G. Babashkina, D.A. Safin, K. Robeyns and Y. Garcia, J. Chem Soc., Dalton Trans., 41, 1451 (2012).
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- J.W. McFarland and R.W. Houser, J. Org. Chem., 33, 340 (1968).
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- A.M. Bowser and J.S. Madalengoitia, Org. Lett., 6, 3409 (2004).
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References
A.-F. Li, J.-H. Wang, F. Wang and Y.-B. Jiang, Chem. Soc. Rev., 39, 3729 (2010).
S. Nishizawa, K. Shigemori and N. Teramae, Chem. Lett., 1185 (1999).
F.D. Sokolov, D.A. Safin, M.G. Babashkina, N.G. Zabirov, V.V. Brusko, N.A. Mironov, D.B. Krivolapov, I.A. Litvinov, R.A. Cherkasov and B.N. Solomonov, Polyhedron, 26, 1550 (2007).
T. Hayashita, T. Onodera, R. Kato, S. Nishizawa and N. Terarnae, Chem. Commun., 755 (2000).
B. Wu, G.-G. Liu, M.-Q. Li, Y. Zhang, S.-Y. Zhang, J.-R. Qiu, X.-P. Xu, S.-J. Ji and X.-W. Wang, Chem. Commun., 3992 (2011).
Z. Ning, C. Yuan, H. Tian, Y. Fu, L. Li, L. Sun and H. Ågren, J. Mater. Chem., 22, 6032 (2012).
M.G. Babashkina, D.A. Safin, K. Robeyns and Y. Garcia, J. Chem Soc., Dalton Trans., 41, 1451 (2012).
W.-X. Liu, R. Yang and A.-F. Li, Z. Li, Y.F. Gao, X.X. Luo, Y.B. Ruan and Y.B. Jiang, Org. Biomol. Chem., 7, 4021 (2009).
J.W. McFarland and R.W. Houser, J. Org. Chem., 33, 340 (1968).
J.W. McFarland, T.H. Kozel, K.R. Stuhlmacher and T.S. Chevalier, J. Heterocycl. Chem., 17, 273 (1980).
C. Levallet, J. Lerpiniere and S.Y. Ko, Tetrahedron, 53, 5291 (1997).
A.M. Bowser and J.S. Madalengoitia, Org. Lett., 6, 3409 (2004).
I.-J. Kang, L.-W. Wang, S.-J. Hsu, C.-C. Lee, Y.-C. Lee, Y.-S. Wu, T.-A. Hsu, A. Yueh, Y.-S. Chao and J.-H. Chern, Bioorg. Med. Chem. Lett., 19, 4134 (2009).
H.-B. Zhang, Y.-A. Zhang, G.-Z. Wu, J.-P. Zhou, W.-L. Huang and X.-W. Hu, Bioorg. Med. Chem. Lett., 19, 1740 (2009).
K.-H. König, C. Holzner and J. Boßlet, Chem. Ber., 121, 1771 (1988).
J. Li, G. Zhang, Z. Zhang and E. Fan, J. Org. Chem., 68, 1611 (2003).
S.A.F. Rostom, Bioorg. Med. Chem., 14, 6475 (2006).
C.-W. Ding, M.-J. Zhang and N. Ma, Youji Huaxue, 30, 173 (2010).
C.-W. Ding, M.-J. Zhang and N. Ma, Chin. Chem. Lett., 20, 1166 (2009).
Z. Aksac, E. Pinar and S. Icli, Org. Magn. Reson., 21, 548 (1983).