Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Water-Mediated Ceric Ammonium Nitrate Catalyzed C-C/C-N Bond Formation: Convenient Access to Polyfunctionalized Pyrazoles via Multicomponent Reaction
Corresponding Author(s) : Raghunath B. Bhosale
Asian Journal of Chemistry,
Vol. 31 No. 5 (2019): Vol 31 Issue 5
Abstract
An efficient multicomponent approach has been developed in the environmentally green aqueous medium for synthesis of substituted polyfunctionalized pyrazoles. The simple and readily available aldehydes, malononitrile and phenylhydrazines substrates afforded polysubstituted imidazoles (15 examples) up to 96 % yield. The polyethylene glycol is playing the dual role of solvent and promoter with water in this reaction catalyzed by ceric ammonium nitrate.
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- J.-J. Liu, M. Zhao, X. Zhang, X. Zhao and H.-L. Zhu, Mini Rev. Med. Chem., 13, 1957 (2013); https://doi.org/10.2174/13895575113139990078.
- V. Kumar, K. Kaur, G.K. Gupta and A.K. Sharma, Eur. J. Med. Chem., 69, 735 (2013); https://doi.org/10.1016/j.ejmech.2013.08.053.
- J. Dwivedi, S. Sharma, S. Jain and A. Singh, Mini Rev. Med. Chem., 18, 918 (2018); https://doi.org/10.2174/1389557517666170927160919.
- S. Ganguly and S.K. Jacob, Mini Rev. Med. Chem., 17, 959 (2017); https://doi.org/10.2174/1389557516666151120115302.
- M.F. Khan, M.M. Alam, G. Verma, W. Akhtar, M. Akhter and M. Shaquiquzzaman, Eur. J. Med. Chem., 120, 170 (2016); https://doi.org/10.1016/j.ejmech.2016.04.077.
- T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997); https://doi.org/10.1021/jm960803q.
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- H.A. DeWald, S. Lobbestael and B.P.H. Poschel, J. Med. Chem., 24, 982 (1981); https://doi.org/10.1021/jm00140a013.
- M. Kim, C. Sim, D. Shin, E. Suh and K. Cho, Crop Prot., 25, 542 (2006); https://doi.org/10.1016/j.cropro.2005.08.010.
- R.E. Sammelson and J.E. Casida, J. Org. Chem., 68, 8075 (2003); https://doi.org/10.1021/jo034520z.
- D. Marcic, Exp. Appl. Acarol., 36, 177 (2005); https://doi.org/10.1007/s10493-005-3579-2.
- V. Nair, J. Mathew, J. Prabhakaran and R. Ruzziconi, Chem. Soc. Rev., 26, 127 (1997); https://doi.org/10.1039/CS9972600127.
- V. Nair, L. Balagopal, R. Rajan and J. Mathew, Acc. Chem. Res., 37, 21 (2004); https://doi.org/10.1021/ar030002z.
- S.B. Panicker, L.G. Nair, T.G. George and A. Augustine, Synlett., 2003, 156 (2003); https://doi.org/10.1055/s-2003-36775.
- A. Dhakshinamoorthy, Synlett, 2005, 3014 (2005); https://doi.org/10.1055/s-2005-921893.
- G.A. Molander, Chem. Rev., 92, 29 (1992); https://doi.org/10.1021/cr00009a002.
- B.B. Nayak, S. Sahu, S. Patel, S. Dash and B.K. Mishra, Indian J. Chem., 47A, 1486 (2008).
- V. Nair, L. Balagopal, R. Rajan and J. Mathew, Acc. Chem. Res., 37, 21 (2004); https://doi.org/10.1021/ar030002z.
- V. Nair and A. Deepthi, Chem. Rev., 107, 1862 (2007); https://doi.org/10.1021/cr068408n.
- T.J. Demars, M.K. Bera, S. Seifert, M.R. Antonio and R.J. Ellis, Angew. Chem. Int. Ed., 54, 7534 (2015); https://doi.org/10.1002/anie.201502336.
- X. Zeng, S. Ji and S. Wang, Tetrahedron, 61, 10235 (2005); https://doi.org/10.1016/j.tet.2005.08.040.
- S.Y. Wang and S.J. Ji, Tetrahedron, 62, 1527 (2006); https://doi.org/10.1016/j.tet.2005.11.011.
- G. Savitha and P.T. Perumal, Tetrahedron Lett., 47, 3589 (2006); https://doi.org/10.1016/j.tetlet.2006.03.046.
- V. Nair, K. Mohanan, T.D. Suja and E. Suresh, Tetrahedron Lett., 47, 705 (2006); https://doi.org/10.1016/j.tetlet.2005.11.115.
- R. Varala, R. Enugala, S. Nuvula and S.R. Adapa, Synlett, 2006, 1009 (2006); https://doi.org/10.1055/s-2006-939066.
- V. Sridharan, C. Avendaño and J.C. Menéndez, Tetrahedron, 63, 673 (2007); https://doi.org/10.1016/j.tet.2006.11.002.
- D.E. Bergbreiter, J. Tian and C. Hongfa, Chem. Rev., 109, 530 (2009); https://doi.org/10.1021/cr8004235.
- N.R. Candeias, L.C. Branco, P.M.P. Gois, C.A.M. Afonso and A.F. Trindade, Chem. Rev., 109, 2703 (2009); https://doi.org/10.1021/cr800462w.
- Z. Andrade and L. Alves, Curr. Org. Chem., 9, 195 (2005); https://doi.org/10.2174/1385272053369178.
- J. Chen, S.K. Spear, J.G. Huddleston and R.D. Rogers, Green Chem., 7, 64 (2005); https://doi.org/10.1039/b413546f.
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- R.D. Rogers, A.H. Bond and C.B. Bauer, Sep. Sci. Technol, 28, 139 (1993); https://doi.org/10.1080/01496399308019483.
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- R.D. Rogers, A.H. Bond and J.L. Wolff, J. Coord. Chem., 29, 187 (1993); https://doi.org/10.1080/00958979308037425.
- R.D. Rogers, A.H. Bond, S. Aguinaga and A. Reyes, J. Am. Chem. Soc., 114, 2967 (1992); https://doi.org/10.1021/ja00034a032.
- R.D. Rogers, A.H. Bond and D.M. Roden, Inorg. Chem., 35, 6964 (1996); https://doi.org/10.1021/ic960587b.
- R.D. Rogers, J. Zhang and C.B. Bauer, J. Alloys Compd., 249, 41 (1997); https://doi.org/10.1016/S0925-8388(96)02640-0.
- H.D. Willauer, J.G. Huddleston and R.D. Rogers, Ind. Eng. Chem. Res., 41, 1892 (2002); https://doi.org/10.1021/ie010598z.
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- H.D. Willauer, J.G. Huddleston, S.T. Griffin and R.D. Rogers, Sep. Sci. Technol., 34, 1069 (1999); https://doi.org/10.1080/01496399908951081.
- H.D. Willauer, J.G. Huddleston and R.D. Rogers, Ind. Eng. Chem. Res., 41, 2591 (2002); https://doi.org/10.1021/ie0107800.
- J.G. Huddleston, H.D. Willauer, R.D. Rogers, R.D. Rogers, P. Gaillard, P.-A. Carrupt, B. Testa and M.H. Abraham, Phys. Chem. Chem. Phys., 4, 4065 (2002); https://doi.org/10.1039/B203018G.
References
J.-J. Liu, M. Zhao, X. Zhang, X. Zhao and H.-L. Zhu, Mini Rev. Med. Chem., 13, 1957 (2013); https://doi.org/10.2174/13895575113139990078.
V. Kumar, K. Kaur, G.K. Gupta and A.K. Sharma, Eur. J. Med. Chem., 69, 735 (2013); https://doi.org/10.1016/j.ejmech.2013.08.053.
J. Dwivedi, S. Sharma, S. Jain and A. Singh, Mini Rev. Med. Chem., 18, 918 (2018); https://doi.org/10.2174/1389557517666170927160919.
S. Ganguly and S.K. Jacob, Mini Rev. Med. Chem., 17, 959 (2017); https://doi.org/10.2174/1389557516666151120115302.
M.F. Khan, M.M. Alam, G. Verma, W. Akhtar, M. Akhter and M. Shaquiquzzaman, Eur. J. Med. Chem., 120, 170 (2016); https://doi.org/10.1016/j.ejmech.2016.04.077.
T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997); https://doi.org/10.1021/jm960803q.
N.K. Terrett, A.S. Bell, D. Brown and P. Ellis, Bioorg. Med. Chem. Lett., 6, 1819 (1996); https://doi.org/10.1016/0960-894X(96)00323-X.
H.A. DeWald, S. Lobbestael and B.P.H. Poschel, J. Med. Chem., 24, 982 (1981); https://doi.org/10.1021/jm00140a013.
M. Kim, C. Sim, D. Shin, E. Suh and K. Cho, Crop Prot., 25, 542 (2006); https://doi.org/10.1016/j.cropro.2005.08.010.
R.E. Sammelson and J.E. Casida, J. Org. Chem., 68, 8075 (2003); https://doi.org/10.1021/jo034520z.
D. Marcic, Exp. Appl. Acarol., 36, 177 (2005); https://doi.org/10.1007/s10493-005-3579-2.
V. Nair, J. Mathew, J. Prabhakaran and R. Ruzziconi, Chem. Soc. Rev., 26, 127 (1997); https://doi.org/10.1039/CS9972600127.
V. Nair, L. Balagopal, R. Rajan and J. Mathew, Acc. Chem. Res., 37, 21 (2004); https://doi.org/10.1021/ar030002z.
S.B. Panicker, L.G. Nair, T.G. George and A. Augustine, Synlett., 2003, 156 (2003); https://doi.org/10.1055/s-2003-36775.
A. Dhakshinamoorthy, Synlett, 2005, 3014 (2005); https://doi.org/10.1055/s-2005-921893.
G.A. Molander, Chem. Rev., 92, 29 (1992); https://doi.org/10.1021/cr00009a002.
B.B. Nayak, S. Sahu, S. Patel, S. Dash and B.K. Mishra, Indian J. Chem., 47A, 1486 (2008).
V. Nair, L. Balagopal, R. Rajan and J. Mathew, Acc. Chem. Res., 37, 21 (2004); https://doi.org/10.1021/ar030002z.
V. Nair and A. Deepthi, Chem. Rev., 107, 1862 (2007); https://doi.org/10.1021/cr068408n.
T.J. Demars, M.K. Bera, S. Seifert, M.R. Antonio and R.J. Ellis, Angew. Chem. Int. Ed., 54, 7534 (2015); https://doi.org/10.1002/anie.201502336.
X. Zeng, S. Ji and S. Wang, Tetrahedron, 61, 10235 (2005); https://doi.org/10.1016/j.tet.2005.08.040.
S.Y. Wang and S.J. Ji, Tetrahedron, 62, 1527 (2006); https://doi.org/10.1016/j.tet.2005.11.011.
G. Savitha and P.T. Perumal, Tetrahedron Lett., 47, 3589 (2006); https://doi.org/10.1016/j.tetlet.2006.03.046.
V. Nair, K. Mohanan, T.D. Suja and E. Suresh, Tetrahedron Lett., 47, 705 (2006); https://doi.org/10.1016/j.tetlet.2005.11.115.
R. Varala, R. Enugala, S. Nuvula and S.R. Adapa, Synlett, 2006, 1009 (2006); https://doi.org/10.1055/s-2006-939066.
V. Sridharan, C. Avendaño and J.C. Menéndez, Tetrahedron, 63, 673 (2007); https://doi.org/10.1016/j.tet.2006.11.002.
D.E. Bergbreiter, J. Tian and C. Hongfa, Chem. Rev., 109, 530 (2009); https://doi.org/10.1021/cr8004235.
N.R. Candeias, L.C. Branco, P.M.P. Gois, C.A.M. Afonso and A.F. Trindade, Chem. Rev., 109, 2703 (2009); https://doi.org/10.1021/cr800462w.
Z. Andrade and L. Alves, Curr. Org. Chem., 9, 195 (2005); https://doi.org/10.2174/1385272053369178.
J. Chen, S.K. Spear, J.G. Huddleston and R.D. Rogers, Green Chem., 7, 64 (2005); https://doi.org/10.1039/b413546f.
R.D. Rogers, A.H. Bond, C.B. Bauer, J. Zhang, M.L. Jezl, D.M. Roden, S.D. Rein and R.R. Chomko, eds.: R.D. Rogers and M.A. Eiteman, Aqueous Biphasic Separations: Biomolecules to Metal Ions, Plenum: New York (1995).
J.G. Huddleston, H.D. Willauer, K.R. Boaz and R.D. Rogers, J. Chromatogr. B: Biomed. Appl., 711, 237 (1998); https://doi.org/10.1016/S0378-4347(97)00662-2.
R.D. Rogers, H.D. Willauer, S.T. Griffin and J.G. Huddleston, J. Chromatogr. B: Biomed. Appl., 711, 255 (1998); https://doi.org/10.1016/S0378-4347(97)00661-0.
R.D. Rogers, A.H. Bond, J. Zhang and C.B. Bauer, Appl. Radiat. Isot., 47, 497 (1996); https://doi.org/10.1016/0969-8043(95)00335-5.
R.D. Rogers, A.H. Bond, C.B. Bauer, J. Zhang, S.D. Rein, R.R. Chomko and D.M. Roden, Solvent Extr. Ion Exch., 13, 689 (1995); https://doi.org/10.1080/07366299508918298.
R.D. Rogers, A.H. Bond and C.B. Bauer, Sep. Sci. Technol, 28, 139 (1993); https://doi.org/10.1080/01496399308019483.
R.D. Rogers, C.B. Bauer and A.H. Bond, Sep. Sci. Technol., 30, 1203 (1995); https://doi.org/10.1080/01496399508010341.
R.D. Rogers, A.H. Bond and J.L. Wolff, J. Coord. Chem., 29, 187 (1993); https://doi.org/10.1080/00958979308037425.
R.D. Rogers, A.H. Bond, S. Aguinaga and A. Reyes, J. Am. Chem. Soc., 114, 2967 (1992); https://doi.org/10.1021/ja00034a032.
R.D. Rogers, A.H. Bond and D.M. Roden, Inorg. Chem., 35, 6964 (1996); https://doi.org/10.1021/ic960587b.
R.D. Rogers, J. Zhang and C.B. Bauer, J. Alloys Compd., 249, 41 (1997); https://doi.org/10.1016/S0925-8388(96)02640-0.
H.D. Willauer, J.G. Huddleston and R.D. Rogers, Ind. Eng. Chem. Res., 41, 1892 (2002); https://doi.org/10.1021/ie010598z.
J.G. Huddleston, H.D. Willauer and R.D. Rogers, J. Chromatogr. B: Biomed. Sci. Appl., 743, 137 (2000); https://doi.org/10.1016/S0378-4347(00)00230-9.
H.D. Willauer, J.G. Huddleston, S.T. Griffin and R.D. Rogers, Sep. Sci. Technol., 34, 1069 (1999); https://doi.org/10.1080/01496399908951081.
H.D. Willauer, J.G. Huddleston and R.D. Rogers, Ind. Eng. Chem. Res., 41, 2591 (2002); https://doi.org/10.1021/ie0107800.
J.G. Huddleston, H.D. Willauer, R.D. Rogers, R.D. Rogers, P. Gaillard, P.-A. Carrupt, B. Testa and M.H. Abraham, Phys. Chem. Chem. Phys., 4, 4065 (2002); https://doi.org/10.1039/B203018G.