Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
ZrO2 Nanoparticles-Supported Cu2(II)-β-Cyclodextrin Mediated Synthesis of N-2 Substituted Tetrazoles by [2+3] Cycloaddition and Post Tetrazole Alkylation
Corresponding Author(s) : Sheena Shashikanth
Asian Journal of Chemistry,
Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018
Abstract
An efficient one-pot ZrO2 nanoparticles-supported Cu2(II)-β-cyclodextrin promoted [2+3] cycloaddition of benzonitriles and sodium azide followed by post tetrazole alkylation using aralkyl esters for the synthesis of N-2-substituted tetrazoles has been presented. One-pot operation, atom-economical, regioselectivity and good yields are the main advantages of this protocol. From the atom economy, it is clear that, catalyst can be reused up to four times without any appreciable changes in catalytic activity
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- R.J. Herr, Bioorg. Med. Chem., 10, 3379 (2002); https://doi.org/10.1016/S0968-0896(02)00239-0.
- G. Aromí, L.A. Barrios, O. Roubeau and P. Gamez, Coord. Chem. Rev., 255, 485 (2011); https://doi.org/10.1016/j.ccr.2010.10.038.
- T.M. Klapotke, C. Miro Sabate and M. Rasp, J. Mater. Chem., 19, 2240 (2009); https://doi.org/10.1039/b818925k.
- T.M. Klapotke, C.M. Sabate and J. Stierstorfer, New J. Chem., 33, 136 (2009); https://doi.org/10.1039/B812529E.
- L.M. Frija, I.V. Khmelinskii, C. Serpa, I.D. Reva, R. Fausto and M.L. Cristiano, Org. Biomol. Chem., 6, 1046 (2008); https://doi.org/10.1039/b718104c.
- L. Liu and J. Zhang, Macromol. Rapid Commun., 34, 1833 (2013); https://doi.org/10.1002/marc.201300741.
- W.H. Ding, W. Cao, X.J. Zheng, W.J. Ding, J.P. Qiao and L.P. Jin, Dalton Trans., 43, 6429 (2014); https://doi.org/10.1039/C4DT00009A.
- A. Salimbeni, R. Canevotti, F. Paleari, D. Poma, S. Caliari, F. Fici, R. Cirillo, A.R. Renzetti and A. Subissi, J. Med. Chem., 38, 4806 (1995); https://doi.org/10.1021/jm00024a008.
- C. Biot, H. Bauer, R.H. Schirmer and E. Davioud-Charvet, J. Med. Chem., 47, 5972 (2004); https://doi.org/10.1021/jm0497545.
- A.S. Gundugola, K.L. Chandra, E.M. Perchellet, A.M. Waters, J.P. Perchellet and S. Rayat, Bioorg. Med. Chem. Lett., 20, 3920 (2010); https://doi.org/10.1016/j.bmcl.2010.05.012.
- T.R. Swaroop, K.S. Sharath Kumar, M. Palanivelu, S. Chaitanya and K.S. Rangappa, J. Heterocycl. Chem., 51, 1866 (2014); https://doi.org/10.1002/jhet.1864.
- K.H. Narasimhamurthy, S. Chandrappa, K.S. Sharath Kumar, K.B. Harsha, H. Ananda and K.S. Rangappa, RSC Adv., 4, 34479 (2014); https://doi.org/10.1039/C4RA02312A.
- K.H. Narasimhamurthy, S. Chandrappa, K.S.S. Kumar, T.R. Swaroop and K.S. Rangappa, Chem. Lett., 42, 1073 (2013); https://doi.org/10.1246/cl.130432.
- K.S. Sharath Kumar, A. Hanumappa, M. Vetrivel, M. Hegde, Y.R. Girish, T.R. Byregowda, S. Rao, S.C. Raghavan and K.S. Rangappa, Bioorg. Med. Chem. Lett., 25, 3616 (2015); https://doi.org/10.1016/j.bmcl.2015.06.069.
- Y.R. Girish, K.S. Sharath Kumar, K.N. Thimmaiah, K.S. Rangappa and S. Shashikanth, RSC Adv., 5, 75533 (2015); https://doi.org/10.1039/C5RA13891D.
- Y.R. Girish, K.S.S. Kumar, H.S. Manasa and S. Shashikanth, J. Chin. Chem. Soc., 61, 1175 (2014); https://doi.org/10.1002/jccs.201400170.
- Y.R. Girish, K.R. Raghavendra, D. Nagaraja, K.S.S. Kumar and S. Shashikanth, Chin. J. Chem., 33, 181 (2015); https://doi.org/10.1002/cjoc.201400684.
- B. Kaboudin, Y. Abedi and T. Yokomatsu, Eur. J. Org. Chem., 6656 (2011); https://doi.org/10.1002/ejoc.201100994.
- B. Kaboudin, Y. Abedi and T. Yokomatsu, Org. Biomol. Chem., 10, 4543 (2012); https://doi.org/10.1039/c2ob25061f.
- Y.R. Girish, K.S. Sharath Kumar, U. Muddegowda, N.K. Lokanath, K.S. Rangappa and S. Shashikanth, RSC Adv., 4, 55800 (2014); https://doi.org/10.1039/C4RA09970B.
- Z.P. Demko and K.B. Sharpless, J. Org. Chem., 66, 7945 (2001); https://doi.org/10.1021/jo010635w.
- H.F. Klare, M. Oestreich, J. Ito, H. Nishiyama, Y. Ohki and K. Tatsumi, J. Am. Chem. Soc., 133, 3312 (2011); https://doi.org/10.1021/ja111483r.
- D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo and L. Vaccaro, J. Org. Chem., 69, 2896 (2004); https://doi.org/10.1021/jo0499468.
- M.L. Kantam, K.B. Shiva Kumar and K. Phani Raja, J. Mol. Catal. Chem., 247, 186 (2006); https://doi.org/10.1016/j.molcata.2005.11.046.
- G. Qi and Y. Dai, Chin. Chem. Lett., 21, 1029 (2010); https://doi.org/10.1016/j.cclet.2010.05.003.
- M.L. Kantam, V. Balasubrahmanyam and K.B.S. Kumar, Synth. Commun., 36, 1809 (2006); https://doi.org/10.1080/00397910600619630.
- T.M. Potewar, S.A. Siddiqui, R.J. Lahoti and K.V. Srinivasan, Tetrahedron Lett., 48, 1721 (2007); https://doi.org/10.1016/j.tetlet.2007.01.050.
- M. Nasrollahzadeh, Y. Bayat, D. Habibi and S. Moshaee, Tetrahedron Lett., 50, 4435 (2009); https://doi.org/10.1016/j.tetlet.2009.05.048.
- T. Jin, F. Kitahara, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 49, 2824 (2008); https://doi.org/10.1016/j.tetlet.2008.02.115.
- B. Sreedhar, A.S. Kumar and D. Yada, Tetrahedron Lett., 52, 3565 (2011); https://doi.org/10.1016/j.tetlet.2011.04.094.
- R. Shelkar, A. Singh and J. Nagarkar, Tetrahedron Lett., 54, 106 (2013); https://doi.org/10.1016/j.tetlet.2012.10.116.
- U. Yapuri, S. Palle, O. Gudaparthi, S.R. Narahari, D.K. Rawat, K. Mukkanti and J. Vantikommu, Tetrahedron Lett., 54, 4732 (2013); https://doi.org/10.1016/j.tetlet.2013.06.107.
- P. Mani, A.K. Singh and S.K. Awasthi, Tetrahedron Lett., 55, 1879 (2014); https://doi.org/10.1016/j.tetlet.2014.01.117.
- P. Sivaguru, K. Bhuvaneswari, R. Ramkumar and A. Lalitha, Tetrahedron Lett., 55, 5683 (2014); https://doi.org/10.1016/j.tetlet.2014.08.066.
- J. Roh, K. Vávrová and A. Hrabálek, Tetrahedron Lett., 51, 1411 (2010); https://doi.org/10.1016/j.tetlet.2010.01.021.
- Y.S. Gyoung, J.-G. Shim and Y. Yamamoto, Tetrahedron Lett., 41, 4193 (2000); https://doi.org/10.1016/S0040-4039(00)00563-3.
- T. Imai, R. Harigae, K. Moriyama and H. Togo, J. Org. Chem., 81, 3975 (2016); https://doi.org/10.1021/acs.joc.6b00606.
- Y.A. Efimova, T.V. Artamonova and G.I. Koldobskii, Russ. J. Org. Chem., 45, 725 (2009); https://doi.org/10.1134/S1070428009050133.
- R.S. Stepanov and L.A. Kruglyakova, Russ. J. Gen. Chem., 85, 1040 (2015); https://doi.org/10.1134/S1070363215050059.
References
R.J. Herr, Bioorg. Med. Chem., 10, 3379 (2002); https://doi.org/10.1016/S0968-0896(02)00239-0.
G. Aromí, L.A. Barrios, O. Roubeau and P. Gamez, Coord. Chem. Rev., 255, 485 (2011); https://doi.org/10.1016/j.ccr.2010.10.038.
T.M. Klapotke, C. Miro Sabate and M. Rasp, J. Mater. Chem., 19, 2240 (2009); https://doi.org/10.1039/b818925k.
T.M. Klapotke, C.M. Sabate and J. Stierstorfer, New J. Chem., 33, 136 (2009); https://doi.org/10.1039/B812529E.
L.M. Frija, I.V. Khmelinskii, C. Serpa, I.D. Reva, R. Fausto and M.L. Cristiano, Org. Biomol. Chem., 6, 1046 (2008); https://doi.org/10.1039/b718104c.
L. Liu and J. Zhang, Macromol. Rapid Commun., 34, 1833 (2013); https://doi.org/10.1002/marc.201300741.
W.H. Ding, W. Cao, X.J. Zheng, W.J. Ding, J.P. Qiao and L.P. Jin, Dalton Trans., 43, 6429 (2014); https://doi.org/10.1039/C4DT00009A.
A. Salimbeni, R. Canevotti, F. Paleari, D. Poma, S. Caliari, F. Fici, R. Cirillo, A.R. Renzetti and A. Subissi, J. Med. Chem., 38, 4806 (1995); https://doi.org/10.1021/jm00024a008.
C. Biot, H. Bauer, R.H. Schirmer and E. Davioud-Charvet, J. Med. Chem., 47, 5972 (2004); https://doi.org/10.1021/jm0497545.
A.S. Gundugola, K.L. Chandra, E.M. Perchellet, A.M. Waters, J.P. Perchellet and S. Rayat, Bioorg. Med. Chem. Lett., 20, 3920 (2010); https://doi.org/10.1016/j.bmcl.2010.05.012.
T.R. Swaroop, K.S. Sharath Kumar, M. Palanivelu, S. Chaitanya and K.S. Rangappa, J. Heterocycl. Chem., 51, 1866 (2014); https://doi.org/10.1002/jhet.1864.
K.H. Narasimhamurthy, S. Chandrappa, K.S. Sharath Kumar, K.B. Harsha, H. Ananda and K.S. Rangappa, RSC Adv., 4, 34479 (2014); https://doi.org/10.1039/C4RA02312A.
K.H. Narasimhamurthy, S. Chandrappa, K.S.S. Kumar, T.R. Swaroop and K.S. Rangappa, Chem. Lett., 42, 1073 (2013); https://doi.org/10.1246/cl.130432.
K.S. Sharath Kumar, A. Hanumappa, M. Vetrivel, M. Hegde, Y.R. Girish, T.R. Byregowda, S. Rao, S.C. Raghavan and K.S. Rangappa, Bioorg. Med. Chem. Lett., 25, 3616 (2015); https://doi.org/10.1016/j.bmcl.2015.06.069.
Y.R. Girish, K.S. Sharath Kumar, K.N. Thimmaiah, K.S. Rangappa and S. Shashikanth, RSC Adv., 5, 75533 (2015); https://doi.org/10.1039/C5RA13891D.
Y.R. Girish, K.S.S. Kumar, H.S. Manasa and S. Shashikanth, J. Chin. Chem. Soc., 61, 1175 (2014); https://doi.org/10.1002/jccs.201400170.
Y.R. Girish, K.R. Raghavendra, D. Nagaraja, K.S.S. Kumar and S. Shashikanth, Chin. J. Chem., 33, 181 (2015); https://doi.org/10.1002/cjoc.201400684.
B. Kaboudin, Y. Abedi and T. Yokomatsu, Eur. J. Org. Chem., 6656 (2011); https://doi.org/10.1002/ejoc.201100994.
B. Kaboudin, Y. Abedi and T. Yokomatsu, Org. Biomol. Chem., 10, 4543 (2012); https://doi.org/10.1039/c2ob25061f.
Y.R. Girish, K.S. Sharath Kumar, U. Muddegowda, N.K. Lokanath, K.S. Rangappa and S. Shashikanth, RSC Adv., 4, 55800 (2014); https://doi.org/10.1039/C4RA09970B.
Z.P. Demko and K.B. Sharpless, J. Org. Chem., 66, 7945 (2001); https://doi.org/10.1021/jo010635w.
H.F. Klare, M. Oestreich, J. Ito, H. Nishiyama, Y. Ohki and K. Tatsumi, J. Am. Chem. Soc., 133, 3312 (2011); https://doi.org/10.1021/ja111483r.
D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo and L. Vaccaro, J. Org. Chem., 69, 2896 (2004); https://doi.org/10.1021/jo0499468.
M.L. Kantam, K.B. Shiva Kumar and K. Phani Raja, J. Mol. Catal. Chem., 247, 186 (2006); https://doi.org/10.1016/j.molcata.2005.11.046.
G. Qi and Y. Dai, Chin. Chem. Lett., 21, 1029 (2010); https://doi.org/10.1016/j.cclet.2010.05.003.
M.L. Kantam, V. Balasubrahmanyam and K.B.S. Kumar, Synth. Commun., 36, 1809 (2006); https://doi.org/10.1080/00397910600619630.
T.M. Potewar, S.A. Siddiqui, R.J. Lahoti and K.V. Srinivasan, Tetrahedron Lett., 48, 1721 (2007); https://doi.org/10.1016/j.tetlet.2007.01.050.
M. Nasrollahzadeh, Y. Bayat, D. Habibi and S. Moshaee, Tetrahedron Lett., 50, 4435 (2009); https://doi.org/10.1016/j.tetlet.2009.05.048.
T. Jin, F. Kitahara, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 49, 2824 (2008); https://doi.org/10.1016/j.tetlet.2008.02.115.
B. Sreedhar, A.S. Kumar and D. Yada, Tetrahedron Lett., 52, 3565 (2011); https://doi.org/10.1016/j.tetlet.2011.04.094.
R. Shelkar, A. Singh and J. Nagarkar, Tetrahedron Lett., 54, 106 (2013); https://doi.org/10.1016/j.tetlet.2012.10.116.
U. Yapuri, S. Palle, O. Gudaparthi, S.R. Narahari, D.K. Rawat, K. Mukkanti and J. Vantikommu, Tetrahedron Lett., 54, 4732 (2013); https://doi.org/10.1016/j.tetlet.2013.06.107.
P. Mani, A.K. Singh and S.K. Awasthi, Tetrahedron Lett., 55, 1879 (2014); https://doi.org/10.1016/j.tetlet.2014.01.117.
P. Sivaguru, K. Bhuvaneswari, R. Ramkumar and A. Lalitha, Tetrahedron Lett., 55, 5683 (2014); https://doi.org/10.1016/j.tetlet.2014.08.066.
J. Roh, K. Vávrová and A. Hrabálek, Tetrahedron Lett., 51, 1411 (2010); https://doi.org/10.1016/j.tetlet.2010.01.021.
Y.S. Gyoung, J.-G. Shim and Y. Yamamoto, Tetrahedron Lett., 41, 4193 (2000); https://doi.org/10.1016/S0040-4039(00)00563-3.
T. Imai, R. Harigae, K. Moriyama and H. Togo, J. Org. Chem., 81, 3975 (2016); https://doi.org/10.1021/acs.joc.6b00606.
Y.A. Efimova, T.V. Artamonova and G.I. Koldobskii, Russ. J. Org. Chem., 45, 725 (2009); https://doi.org/10.1134/S1070428009050133.
R.S. Stepanov and L.A. Kruglyakova, Russ. J. Gen. Chem., 85, 1040 (2015); https://doi.org/10.1134/S1070363215050059.