Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Unusual Cleavage of N-N Bond of 1-Arylamino-1,2,3-triazole Derivatives: A Simple and Alternate Approach to 4,5-Disubstituted-1H-1,2,3-triazoles
Corresponding Author(s) : L. Emmanuvel
Asian Journal of Chemistry,
Vol. 31 No. 5 (2019): Vol 31 Issue 5
Abstract
In this communication, the authors described the synthesis of 1-arylamino-1,2,3-triazole derivatives via diazo transfer reaction on active methylene hydrazones. Further, we have observed the reduction of 1-arylamino-1,2,3-triazole using Pd/C, H2 to result in unusual N-N bond cleavage to give 4,5-disubstituted-1H-1,2,3-triazole.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- W. Tuo, N. Leleu-Chavain, J. Spencer, S. Sansook, R. Millet and P. Chavatte, J. Med. Chem., 60, 4 (2017); https://doi.org/10.1021/acs.jmedchem.6b00538.
- L.M. De Coen, T.S.A. Heugebaert, D. García and C.V. Stevens, Chem. Rev., 116, 80 (2016); https://doi.org/10.1021/acs.chemrev.5b00483.
- F. Meyer, Chem. Commun., 52, 3077 (2016); https://doi.org/10.1039/C5CC09414C.
- E.A. Burakova, I.V. Saranina, N.V. Tikunova, Z.K. Nazarkina, P.P. Laktionov, L.A. Karpinskaya, V.B. Anikin, V.V. Zarubaev and V.N. Silnikov, Bioorg. Med. Chem., 24, 6012 (2016); https://doi.org/10.1016/j.bmc.2016.09.064.
- P. Martins, J. Jesus, S. Santos, L.R. Raposo, C. Roma-Rodrigues, P.V. Baptista and A.R. Fernandes, Molecules, 20, 16852 (2015); https://doi.org/10.3390/molecules200916852.
- D.F. Taber and P.K. Tirunahari, Tetrahedron, 67, 7195 (2011); https://doi.org/10.1016/j.tet.2011.06.040.
- X. Li, M. Chen, X. Xie, N. Sun, S. Li and Y. Liu, Org. Lett., 17, 2984 (2015); https://doi.org/10.1021/acs.orglett.5b01281.
- J. Li and L. Neuville, Org. Lett., 15, 6124 (2013); https://doi.org/10.1021/ol4029622.
- J. Thomas, J. John, N. Parekh and W. Dehaen, Angew. Chem. Int. Ed., 126, 10319 (2014); https://doi.org/10.1002/ange.201403453.
- V.S. Pore, M.A. Jagtap, S.G. Agalave, A.K. Pandey, M.I. Siddiqi, V. Kumar and P.K. Shukla, MedChemComm, 3, 484 (2012); https://doi.org/10.1039/c2md00205a.
- O.A. Phillips, E.E. Udo, M.E. Abdel-Hamid and R. Varghese, Eur. J. Med. Chem., 44, 3217 (2009); https://doi.org/10.1016/j.ejmech.2009.03.024.
- W.T. Li, W.H. Wu, C.H. Tang, R. Tai and S.T. Chen, ACS Comb. Sci., 13, 72 (2011); https://doi.org/10.1021/co1000234.
- M.S. Costa, N. Boechat, É.A. Rangel, F.C. da Silva, A.M.T. de Souza, C.R. Rodrigues, H.C. Castro, I.N. Junior, M.C.S. Lourenço, S.M.S.V. Wardell and V.F. Ferreira, Bioorg. Med. Chem., 14, 8644 (2006); https://doi.org/10.1016/j.bmc.2006.08.019.
- R. Huisgen, Angew. Chem., 75, 604 (1963); https://doi.org/10.1002/ange.19630751304.
- P.W. Szafrañski, P. Kasza and M.T. Cegla, Tetrahedron Lett., 56, 6244 (2015); https://doi.org/10.1016/j.tetlet.2015.09.110.
- V.D. Bock, H. Hiemstra and J.H. Van Maarseveen, Eur. J. Org. Chem., 2006, 51 (2006); https://doi.org/10.1002/ejoc.200500483.
- S.G. Hansen and H.H. Jensen, Synlett, 3275 (2009); https://doi.org/10.1055/s-0029-1218366.
- P. Thirumurugan, D. Matosiuk and K. Jozwiak, Chem. Rev., 113, 4905 (2013); https://doi.org/10.1021/cr200409f.
- I.E. Valverde, A. Bauman, C.A. Kluba, S. Vomstein, M.A. Walter and T.L. Mindt, Angew. Chem. Int. Ed., 52, 8957 (2013); https://doi.org/10.1002/anie.201303108.
- S.G. Agalave, S.R. Maujan and V.S. Pore, Chem. Asian J., 6, 2696 (2011); https://doi.org/10.1002/asia.201100432.
- G. Kaplan, G. Drake, K. Tollison, L. Hall and T. Hawkins, J. Heterocycl. Chem., 42, 19 (2005); https://doi.org/10.1002/jhet.5570420104.
- A.K. Jordão, P.P. Afonso, V.F. Ferreira, M.C.B.V. de Souza, M.C.B. Almeida, C.O. Beltrame, D.P. Paiva, S.M.S.V. Wardell, J.L. Wardell, E.R.T. Tiekink, C.R. Damaso and A.C. Cunha, Eur. J. Med. Chem., 44, 3777 (2009); https://doi.org/10.1016/j.ejmech.2009.04.046.
- R. Nagarajan, J. Jayashankaran and L. Emmanuvel, Tetrahedron Lett., 57, 2612 (2016); https://doi.org/10.1016/j.tetlet.2016.04.112.
- K. Sarker, R. Patel, C. Dadida, and D. J. Sen, World. J. Pharm. Res., 4, 2191 (2015).
- T. Schabel, C. Belger and B. Plietker, Org. Lett., 15, 2858 (2013); https://doi.org/10.1021/ol401185t.
- C.W. Cheung and X. Hu, Nat. Commun., 7, 12494 (2016); https://doi.org/10.1038/ncomms12494.
- F. Li, B. Frett and H. Li, Synlett, 25, 1403 (2014); https://doi.org/10.1055/s-0033-1339025.
- R. Adams, F.L. Cohen and O.W. Rees, J. Am. Chem. Soc., 49, 1093 (1927); https://doi.org/10.1021/ja01403a035.
- T.L. Gilchrist, D. Hughes and R. Wasson, Tetrahedron Lett., 28, 1573 (1987); https://doi.org/10.1016/S0040-4039(01)81045-5.
- P.A. Jacobi, M.J. Martinelli and S. Polanc, J. Am. Chem. Soc., 106, 5594 (1984); https://doi.org/10.1021/ja00331a032.
- P. Magnus, N. Garizi, K.A. Seibert and A. Ornholt, Org. Lett., 11, 5646 (2009); https://doi.org/10.1021/ol902313v.
- Q. Tang, C. Zhang and M. Luo, J. Am. Chem. Soc., 130, 5840 (2008); https://doi.org/10.1021/ja711153b.
- Y. Tang, H. Yang, X. Ju, H. Huang, C. Lu and G. Cheng, J. Mater. Chem., 2, 4127 (2014); https://doi.org/10.1039/c3ta14485b.
- I. Pogorelic, M. Filipan-Litvic, S. Merkaš, G. Ljubic, I. Cepanec and M. Litvic, J. Mol. Catal. Chem., 274, 202 (2007); https://doi.org/10.1016/j.molcata.2007.05.020.
References
W. Tuo, N. Leleu-Chavain, J. Spencer, S. Sansook, R. Millet and P. Chavatte, J. Med. Chem., 60, 4 (2017); https://doi.org/10.1021/acs.jmedchem.6b00538.
L.M. De Coen, T.S.A. Heugebaert, D. García and C.V. Stevens, Chem. Rev., 116, 80 (2016); https://doi.org/10.1021/acs.chemrev.5b00483.
F. Meyer, Chem. Commun., 52, 3077 (2016); https://doi.org/10.1039/C5CC09414C.
E.A. Burakova, I.V. Saranina, N.V. Tikunova, Z.K. Nazarkina, P.P. Laktionov, L.A. Karpinskaya, V.B. Anikin, V.V. Zarubaev and V.N. Silnikov, Bioorg. Med. Chem., 24, 6012 (2016); https://doi.org/10.1016/j.bmc.2016.09.064.
P. Martins, J. Jesus, S. Santos, L.R. Raposo, C. Roma-Rodrigues, P.V. Baptista and A.R. Fernandes, Molecules, 20, 16852 (2015); https://doi.org/10.3390/molecules200916852.
D.F. Taber and P.K. Tirunahari, Tetrahedron, 67, 7195 (2011); https://doi.org/10.1016/j.tet.2011.06.040.
X. Li, M. Chen, X. Xie, N. Sun, S. Li and Y. Liu, Org. Lett., 17, 2984 (2015); https://doi.org/10.1021/acs.orglett.5b01281.
J. Li and L. Neuville, Org. Lett., 15, 6124 (2013); https://doi.org/10.1021/ol4029622.
J. Thomas, J. John, N. Parekh and W. Dehaen, Angew. Chem. Int. Ed., 126, 10319 (2014); https://doi.org/10.1002/ange.201403453.
V.S. Pore, M.A. Jagtap, S.G. Agalave, A.K. Pandey, M.I. Siddiqi, V. Kumar and P.K. Shukla, MedChemComm, 3, 484 (2012); https://doi.org/10.1039/c2md00205a.
O.A. Phillips, E.E. Udo, M.E. Abdel-Hamid and R. Varghese, Eur. J. Med. Chem., 44, 3217 (2009); https://doi.org/10.1016/j.ejmech.2009.03.024.
W.T. Li, W.H. Wu, C.H. Tang, R. Tai and S.T. Chen, ACS Comb. Sci., 13, 72 (2011); https://doi.org/10.1021/co1000234.
M.S. Costa, N. Boechat, É.A. Rangel, F.C. da Silva, A.M.T. de Souza, C.R. Rodrigues, H.C. Castro, I.N. Junior, M.C.S. Lourenço, S.M.S.V. Wardell and V.F. Ferreira, Bioorg. Med. Chem., 14, 8644 (2006); https://doi.org/10.1016/j.bmc.2006.08.019.
R. Huisgen, Angew. Chem., 75, 604 (1963); https://doi.org/10.1002/ange.19630751304.
P.W. Szafrañski, P. Kasza and M.T. Cegla, Tetrahedron Lett., 56, 6244 (2015); https://doi.org/10.1016/j.tetlet.2015.09.110.
V.D. Bock, H. Hiemstra and J.H. Van Maarseveen, Eur. J. Org. Chem., 2006, 51 (2006); https://doi.org/10.1002/ejoc.200500483.
S.G. Hansen and H.H. Jensen, Synlett, 3275 (2009); https://doi.org/10.1055/s-0029-1218366.
P. Thirumurugan, D. Matosiuk and K. Jozwiak, Chem. Rev., 113, 4905 (2013); https://doi.org/10.1021/cr200409f.
I.E. Valverde, A. Bauman, C.A. Kluba, S. Vomstein, M.A. Walter and T.L. Mindt, Angew. Chem. Int. Ed., 52, 8957 (2013); https://doi.org/10.1002/anie.201303108.
S.G. Agalave, S.R. Maujan and V.S. Pore, Chem. Asian J., 6, 2696 (2011); https://doi.org/10.1002/asia.201100432.
G. Kaplan, G. Drake, K. Tollison, L. Hall and T. Hawkins, J. Heterocycl. Chem., 42, 19 (2005); https://doi.org/10.1002/jhet.5570420104.
A.K. Jordão, P.P. Afonso, V.F. Ferreira, M.C.B.V. de Souza, M.C.B. Almeida, C.O. Beltrame, D.P. Paiva, S.M.S.V. Wardell, J.L. Wardell, E.R.T. Tiekink, C.R. Damaso and A.C. Cunha, Eur. J. Med. Chem., 44, 3777 (2009); https://doi.org/10.1016/j.ejmech.2009.04.046.
R. Nagarajan, J. Jayashankaran and L. Emmanuvel, Tetrahedron Lett., 57, 2612 (2016); https://doi.org/10.1016/j.tetlet.2016.04.112.
K. Sarker, R. Patel, C. Dadida, and D. J. Sen, World. J. Pharm. Res., 4, 2191 (2015).
T. Schabel, C. Belger and B. Plietker, Org. Lett., 15, 2858 (2013); https://doi.org/10.1021/ol401185t.
C.W. Cheung and X. Hu, Nat. Commun., 7, 12494 (2016); https://doi.org/10.1038/ncomms12494.
F. Li, B. Frett and H. Li, Synlett, 25, 1403 (2014); https://doi.org/10.1055/s-0033-1339025.
R. Adams, F.L. Cohen and O.W. Rees, J. Am. Chem. Soc., 49, 1093 (1927); https://doi.org/10.1021/ja01403a035.
T.L. Gilchrist, D. Hughes and R. Wasson, Tetrahedron Lett., 28, 1573 (1987); https://doi.org/10.1016/S0040-4039(01)81045-5.
P.A. Jacobi, M.J. Martinelli and S. Polanc, J. Am. Chem. Soc., 106, 5594 (1984); https://doi.org/10.1021/ja00331a032.
P. Magnus, N. Garizi, K.A. Seibert and A. Ornholt, Org. Lett., 11, 5646 (2009); https://doi.org/10.1021/ol902313v.
Q. Tang, C. Zhang and M. Luo, J. Am. Chem. Soc., 130, 5840 (2008); https://doi.org/10.1021/ja711153b.
Y. Tang, H. Yang, X. Ju, H. Huang, C. Lu and G. Cheng, J. Mater. Chem., 2, 4127 (2014); https://doi.org/10.1039/c3ta14485b.
I. Pogorelic, M. Filipan-Litvic, S. Merkaš, G. Ljubic, I. Cepanec and M. Litvic, J. Mol. Catal. Chem., 274, 202 (2007); https://doi.org/10.1016/j.molcata.2007.05.020.