Copper(I) Catalyzed Azide-Alkyne Click Reaction: Synthesis and Metal-Ion Binding Studies of Some 1,2,3-Triazole Derivatives

Harinder Singh; Vinod Kumar

doi:10.14233/ajchem.2016.19431

Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Issue Published : December 5, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Copper(I) Catalyzed Azide-Alkyne Click Reaction: Synthesis and Metal-Ion Binding Studies of Some 1,2,3-Triazole Derivatives

https://doi.org/10.14233/ajchem.2016.19431

Harinder Singh

Department of Chemistry, Maharishi Markandeshwar University, Mullana, Ambala-133 207, India

Vinod Kumar

Department of Chemistry, Maharishi Markandeshwar University, Mullana, Ambala-133 207, India

Corresponding Author(s) : Vinod Kumar

vinodbatan@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 3 (2016): Vol 28 Issue 3
Article Published : December 5, 2015

Abstract

Click chemistry involving 1,3-dipolar cycloaddition reaction of an azide and a terminal alkyne has gained much attention in the field of science to design new materials for various applications. Recently, ability of 1,2,3-triazole ring to participate in complexation with metal ions has been recognized. The demand for selective receptors for specific cations especially sensors that monitor toxic heavy metal ions selectively have been continuously increasing. Therefore, we report herein, the synthesis of some 1,2,3-triazole derivatives through the click reaction. All the newly synthesized compounds thus obtained have been characterized by IR, ¹H NMR, ¹³C NMR and mass spectral studies and screened for their recognition properties towards various metal ions.

Keywords

Click reaction Binding studies Chemosensor

Singh, H., & Kumar, V. (2015). Copper(I) Catalyzed Azide-Alkyne Click Reaction: Synthesis and Metal-Ion Binding Studies of Some 1,2,3-Triazole Derivatives. Asian Journal of Chemistry, 28(3), 613–616. https://doi.org/10.14233/ajchem.2016.19431

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References

(a) E.M. Nolan and S.J. Lippard, Chem. Rev., 108, 3443 (2008); doi:10.1021/cr068000q; (b) H.N. Kim, M.H. Lee, H.J. Kim, J.S. Kim and J. Yoon, Chem. Soc. Rev., 37, 1465 (2008); doi:10.1039/b802497a; (c) E.M. Nolan and S.J. Lippard, Acc. Chem. Res., 42, 193 (2009); doi:10.1021/ar8001409; (d) R.D. Hancock, D.L. Melton, J.M. Harrington, F.C. McDonald, R.T. Gephart, L.L. Boone, S.B. Jones, N.E. Dean, J.R. Whitehead and G.M. Cockrell, Coord. Chem. Rev., 251, 1678 (2007); doi:10.1016/j.ccr.2006.10.007; (e) E. Freisinger and R.K.O. Sigel, Coord. Chem. Rev., 251, 1834 (2007); doi:10.1016/j.ccr.2007.03.008; (f) C. Bargossi, M.C. Fiorini, M. Montalti, L. Prodi and N. Zaccheroni, Coord. Chem. Rev., 208, 17 (2000); doi:10.1016/S0010-8545(00)00252-6; (g) E. Kimura and T. Koike, Chem. Soc. Rev., 27, 179 (1998); doi:10.1039/a827179z.
T.R. Chan, R. Hilgraf, K.B. Sharpless and V.V. Fokin, Org. Lett., 6, 2853 (2004); doi:10.1021/ol0493094.
R. Bronisz, Inorg. Chem., 44, 4463 (2005); doi:10.1021/ic050449z.
T.L. Mindt, H. Struthers, L. Brans, T. Anguelov, C. Schweinsberg, V. Maes, D. Tourwe and B. Schibli, J. Am. Chem. Soc., 128, 15096 (2006); doi:10.1021/ja066779f.
R.J. Detz, S.A. Heras, R. de Gelder, P.W.N.M. van Leeuwen, H. Hiemstra, J.N.H. Reek and J.H. van Maarseveen, Org. Lett., 8, 3227 (2006); doi:10.1021/ol061015q.
C. Ornelas, J. Ruiz Aranzaes, E. Cloutet, S. Alves and D. Astruc, Angew. Chem. Int. Ed., 46, 872 (2007); doi:10.1002/anie.200602858.
Y. Li, J.C. Huffman and A.H. Flood, Chem. Commun., 2692 (2007); doi:10.1039/b703301j.
O. David, S. Maisonneuve and J. Xie, Tetrahedron Lett., 48, 6527 (2007); doi:10.1016/j.tetlet.2007.07.071.
K.-C. Chang, I.-H. Su, A. Senthilvelan and W.-S. Chung, Org. Lett., 9, 3363 (2007); doi:10.1021/ol071337+.
K.-C. Chang, I.-H. Su, G.-H. Lee and W.-S. Chung, Tetrahedron Lett., 48, 7274 (2007); doi:10.1016/j.tetlet.2007.08.045.
B. Colasson, M. Save, P. Milko, J. Roithova, D. Schroder and O. Reinaud, Org. Lett., 9, 4987 (2007); doi:10.1021/ol701850t.
S. Huang, R.J. Clark and L. Zhu, Org. Lett., 9, 4999 (2007); doi:10.1021/ol702208y.
R.M. Meudtner, M. Ostermeier, R. Goddard, C. Limberg and S. Hecht, Chem. Eur. J., 13, 9834 (2007); doi:10.1002/chem.200701240.
T. Ziegler and C. Hermann, Tetrahedron Lett., 49, 2166 (2008); doi:10.1016/j.tetlet.2008.01.081.
D. Schweinfurth, K.I. Hardcastle and U.H.F. Bunz, Chem. Commun., 2203 (2008); doi:10.1039/b800284c.
K. Varazo, F. Xie, D. Gulledge and Q. Wang, Tetrahedron Lett., 49, 5293 (2008); doi:10.1016/j.tetlet.2008.06.092.
M. Obata, A. Kitamura, A. Mori, C. Kameyama, J.A. Czaplewska, R. Tanaka, I. Kinoshita, T. Kusumoto, H. Hashimoto, M. Harada, Y. Mikata, T. Funabiki and S. Yano, Dalton Trans., 3292 (2008); doi:10.1039/b718538c.
S.Y. Park, J.H. Yoon, C.S. Hong, R. Souane, J.S. Kim, S.E. Matthews and J. Vicens, J. Org. Chem., 73, 8212 (2008); doi:10.1021/jo8012918.
E. Tamanini, A. Katewa, L.M. Sedger, M.H. Todd and M. Watkinson, Inorg. Chem., 48, 319 (2009); doi:10.1021/ic8017634.
V. Steinmetz, F. Couty and O.R.P. David, Chem. Commun., 343 (2009); doi:10.1039/B816628E.
M. Juricek, P.H.J. Kouwer, J. Rehak, J. Sly and A.E. Rowan, J. Org. Chem., 74, 21 (2009); doi:10.1021/jo802078f.
J. Zhang, J. Luo, X.X. Zhu, M.J.N. Junk and D. Hinderberger, Langmuir, 26, 2958 (2010); doi:10.1021/la9028996.
S.H. Kim, H.S. Choi, J. Kim, S.J. Lee, D.T. Quang and J.S. Kim, Org. Lett., 12, 560 (2010); doi:10.1021/ol902743s.
R. Huisgen, G. Szeimies and L. Mobius, Chem. Ber., 100, 2494 (1967); doi:10.1002/cber.19671000806.
C.M. Tornoe, C. Christensen and M. Meldal, J. Org. Chem., 67, 3057 (2002); doi:10.1021/jo011148j.
V.V. Rostovtsev, L.G. Green, V.V. Fokin and K.B. Sharpless, Angew. Chem. Int. Ed., 41, 2596 (2002);
doi:10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4.
(a) A.K. Ganai, R. Bhardwaj, S. Hotha, S.S. Gupta and B.L.V. Prasad, New J. Chem., 34, 2662 (2010); doi:10.1039/c0nj00292e; (b) C. Li, X. Liu, M. Yuan, J. Li, Y. Guo, J. Xu, M. Zhu, J. Lv, H. Liu and Y. Li, Langmuir, 23, 6754 (2007); doi:10.1021/la070110k; (c) E.-D. Chenot, J.C. Rodríguez-Domínguez, A. Comel, G. Kirsch and P. Hannewald, J. Heterocycl. Chem., 45, 1429 (2008); doi:10.1002/jhet.5570450528.
H. Benesi and J.H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1949); doi:10.1021/ja01176a030.

References

(a) E.M. Nolan and S.J. Lippard, Chem. Rev., 108, 3443 (2008); doi:10.1021/cr068000q; (b) H.N. Kim, M.H. Lee, H.J. Kim, J.S. Kim and J. Yoon, Chem. Soc. Rev., 37, 1465 (2008); doi:10.1039/b802497a; (c) E.M. Nolan and S.J. Lippard, Acc. Chem. Res., 42, 193 (2009); doi:10.1021/ar8001409; (d) R.D. Hancock, D.L. Melton, J.M. Harrington, F.C. McDonald, R.T. Gephart, L.L. Boone, S.B. Jones, N.E. Dean, J.R. Whitehead and G.M. Cockrell, Coord. Chem. Rev., 251, 1678 (2007); doi:10.1016/j.ccr.2006.10.007; (e) E. Freisinger and R.K.O. Sigel, Coord. Chem. Rev., 251, 1834 (2007); doi:10.1016/j.ccr.2007.03.008; (f) C. Bargossi, M.C. Fiorini, M. Montalti, L. Prodi and N. Zaccheroni, Coord. Chem. Rev., 208, 17 (2000); doi:10.1016/S0010-8545(00)00252-6; (g) E. Kimura and T. Koike, Chem. Soc. Rev., 27, 179 (1998); doi:10.1039/a827179z.

T.R. Chan, R. Hilgraf, K.B. Sharpless and V.V. Fokin, Org. Lett., 6, 2853 (2004); doi:10.1021/ol0493094.

R. Bronisz, Inorg. Chem., 44, 4463 (2005); doi:10.1021/ic050449z.

T.L. Mindt, H. Struthers, L. Brans, T. Anguelov, C. Schweinsberg, V. Maes, D. Tourwe and B. Schibli, J. Am. Chem. Soc., 128, 15096 (2006); doi:10.1021/ja066779f.

R.J. Detz, S.A. Heras, R. de Gelder, P.W.N.M. van Leeuwen, H. Hiemstra, J.N.H. Reek and J.H. van Maarseveen, Org. Lett., 8, 3227 (2006); doi:10.1021/ol061015q.

C. Ornelas, J. Ruiz Aranzaes, E. Cloutet, S. Alves and D. Astruc, Angew. Chem. Int. Ed., 46, 872 (2007); doi:10.1002/anie.200602858.

Y. Li, J.C. Huffman and A.H. Flood, Chem. Commun., 2692 (2007); doi:10.1039/b703301j.

O. David, S. Maisonneuve and J. Xie, Tetrahedron Lett., 48, 6527 (2007); doi:10.1016/j.tetlet.2007.07.071.

K.-C. Chang, I.-H. Su, A. Senthilvelan and W.-S. Chung, Org. Lett., 9, 3363 (2007); doi:10.1021/ol071337+.

K.-C. Chang, I.-H. Su, G.-H. Lee and W.-S. Chung, Tetrahedron Lett., 48, 7274 (2007); doi:10.1016/j.tetlet.2007.08.045.

B. Colasson, M. Save, P. Milko, J. Roithova, D. Schroder and O. Reinaud, Org. Lett., 9, 4987 (2007); doi:10.1021/ol701850t.

S. Huang, R.J. Clark and L. Zhu, Org. Lett., 9, 4999 (2007); doi:10.1021/ol702208y.

R.M. Meudtner, M. Ostermeier, R. Goddard, C. Limberg and S. Hecht, Chem. Eur. J., 13, 9834 (2007); doi:10.1002/chem.200701240.

T. Ziegler and C. Hermann, Tetrahedron Lett., 49, 2166 (2008); doi:10.1016/j.tetlet.2008.01.081.

D. Schweinfurth, K.I. Hardcastle and U.H.F. Bunz, Chem. Commun., 2203 (2008); doi:10.1039/b800284c.

K. Varazo, F. Xie, D. Gulledge and Q. Wang, Tetrahedron Lett., 49, 5293 (2008); doi:10.1016/j.tetlet.2008.06.092.

M. Obata, A. Kitamura, A. Mori, C. Kameyama, J.A. Czaplewska, R. Tanaka, I. Kinoshita, T. Kusumoto, H. Hashimoto, M. Harada, Y. Mikata, T. Funabiki and S. Yano, Dalton Trans., 3292 (2008); doi:10.1039/b718538c.

S.Y. Park, J.H. Yoon, C.S. Hong, R. Souane, J.S. Kim, S.E. Matthews and J. Vicens, J. Org. Chem., 73, 8212 (2008); doi:10.1021/jo8012918.

E. Tamanini, A. Katewa, L.M. Sedger, M.H. Todd and M. Watkinson, Inorg. Chem., 48, 319 (2009); doi:10.1021/ic8017634.

V. Steinmetz, F. Couty and O.R.P. David, Chem. Commun., 343 (2009); doi:10.1039/B816628E.

M. Juricek, P.H.J. Kouwer, J. Rehak, J. Sly and A.E. Rowan, J. Org. Chem., 74, 21 (2009); doi:10.1021/jo802078f.

J. Zhang, J. Luo, X.X. Zhu, M.J.N. Junk and D. Hinderberger, Langmuir, 26, 2958 (2010); doi:10.1021/la9028996.

S.H. Kim, H.S. Choi, J. Kim, S.J. Lee, D.T. Quang and J.S. Kim, Org. Lett., 12, 560 (2010); doi:10.1021/ol902743s.

R. Huisgen, G. Szeimies and L. Mobius, Chem. Ber., 100, 2494 (1967); doi:10.1002/cber.19671000806.

C.M. Tornoe, C. Christensen and M. Meldal, J. Org. Chem., 67, 3057 (2002); doi:10.1021/jo011148j.

V.V. Rostovtsev, L.G. Green, V.V. Fokin and K.B. Sharpless, Angew. Chem. Int. Ed., 41, 2596 (2002);

doi:10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4.

(a) A.K. Ganai, R. Bhardwaj, S. Hotha, S.S. Gupta and B.L.V. Prasad, New J. Chem., 34, 2662 (2010); doi:10.1039/c0nj00292e; (b) C. Li, X. Liu, M. Yuan, J. Li, Y. Guo, J. Xu, M. Zhu, J. Lv, H. Liu and Y. Li, Langmuir, 23, 6754 (2007); doi:10.1021/la070110k; (c) E.-D. Chenot, J.C. Rodríguez-Domínguez, A. Comel, G. Kirsch and P. Hannewald, J. Heterocycl. Chem., 45, 1429 (2008); doi:10.1002/jhet.5570450528.

H. Benesi and J.H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1949); doi:10.1021/ja01176a030.

Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Copper(I) Catalyzed Azide-Alkyne Click Reaction: Synthesis and Metal-Ion Binding Studies of Some 1,2,3-Triazole Derivatives

Corresponding Author(s) : Vinod Kumar

Abstract

Keywords

Full Article

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References

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