Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Zirconium(IV) Oxychloride: A Simple and Efficient Catalyst for the Synthesis of Chromen-2-one Derivatives
Corresponding Author(s) : S. Tasqeeruddin
Asian Journal of Chemistry,
Vol. 32 No. 10 (2020): Vol 32 Issue 10
Abstract
The present work explores a highly efficient, environmental friendly, green protocol for the synthesis of chromen-2-one derivatives (3a-m) by the condensation of salicylaldehydes with various active methylene compounds using zirconium(IV) oxychloride as catalyst. This is a convenient and rapid method for Knoevenagel condensation and this methodology offers several advantages including shorter reaction time, milder conditions, inexpensive catalyst, simple operational procedure and allowed to achieve the desired products in excellent yields. The structures of all the synthesized compounds were confirmed by spectral data.
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- N.T. Patil and Y. Yamamoto, Chem. Rev., 108, 3395 (2008); https://doi.org/10.1021/cr050041j
- H.A. El-Wahab, M.A. El-Fattah, N.A. El-Khalik, H.S. Nassar and M.M. Abdelall, Prog. Org. Coat., 77, 1506 (2014); https://doi.org/10.1016/j.porgcoat.2014.04.026
- Y.K. Al-Majedy, A.A.H. Kadhum, A.A. Al-Amiery and A.B. Mohamad, Sys. Rev. Pharm., 8, 62 (2017); https://doi.org/10.5530/srp.2017.1.11
- R.S. Keri, K.M. Hosamani, H.S. Reddy and R.V. Shingalapur, Arch. Pharm., 343, 237 (2010); https://doi.org/10.1002/ardp.200900188
- F. Chimenti, B. Bizzarri, A. Bolasco, D. Secci, P. Chimenti, A. Granese, S. Carradori, D. Rivanera, A. Zicari, M.M. Scaltrito and F. Sisto, Bioorg. Med. Chem. Lett., 20, 4922 (2010); https://doi.org/10.1016/j.bmcl.2010.06.048
- K.V. Sashidhara, A. Kumar, M. Chatterjee, K.B. Rao, S. Singh, A.K. Verma and G. Palit, Bioorg. Med. Chem. Lett., 21, 1937 (2011); https://doi.org/10.1016/j.bmcl.2011.02.040
- I. Kostova, S. Bhatia, P. Grigorov, S. Balkansky, V. S. Parmar, A. K. Prasad and L. Saso, Curr. Med. Chem., 18, 3929 (2001); https://doi.org/10.2174/092986711803414395
- S.J. Lee, U.S. Lee, W.J. Kim and S.K. Moon, Mol. Med. Rep., 4, 337 (2011); https://doi.org/10.3892/mmr.2011.420
- T.A. De Almeida Barros, L.A.R. De Freitas, J.M.B. Filho, X.P. Nunes, A.M. Giulietti, G.E. De Souza, R.R. Dos Santos, M.B.P. Soares and C.F. Villarreal, J. Pharm. Pharmacol., 62, 205 (2010); https://doi.org/10.1211/jpp.62.02.0008
- X.Y. Huang, Z.J. Shan, H.L. Zhai, L. Su and X.Y. Zhang, Chem. Biol. Drug Des., 78, 651 (2011); https://doi.org/10.1111/j.1747-0285.2011.01195.x
- J.F. Vasconcelos, M.M. Teixeira, J.M. Barbosa-Filho, M.F. Agra, X.P. Nunes, A.M. Giulietti, R. Ribeiro-Dos-Santos and M.B.P. Soares, Eur. J. Pharmacol., 609, 126 (2009); https://doi.org/10.1016/j.ejphar.2009.03.027
- J. Neyts, E.D. Clercq, R. Singha, Y.H. Chang, A.R. Das, S.K. Chakraborty, S.C. Hong, S.-C. Tsay, M.-H. Hsu and J.R. Hwu, J. Med. Chem., 52,1486 (2009); https://doi.org/10.1021/jm801240d
- T.O. Olomola, R. Klein, N. Mautsa, Y. Sayed and P.T. Kaye, Bioorg. Med. Chem., 21, 1964 (2013); https://doi.org/10.1016/j.bmc.2013.01.025
- A. Manvar, A. Bavishi, A. Radadiya, J. Patel, V. Vora, N. Dodia, K. Rawal and A. Shah, Bioorg. Med. Chem. Lett., 21, 4728 (2011); https://doi.org/10.1016/j.bmcl.2011.06.074
- J.-Y. Yeh, M.S. Coumar, J.-T. Horng, H.-Y. Shiao, F.-M. Kuo, H.-L. Lee, I.-C. Chen, C.-W. Chang, W.-F. Tang, S.-N. Tseng, C.-J. Chen, S.-R. Shih, J.T.-A. Hsu, C.-C. Liao, Y.-S. Chao and H.-P. Hsieh, J. Med. Chem., 53, 1519 (2010); https://doi.org/10.1021/jm901570x
- Q. Sun, D. Peng, S. Yang, X. Zhu, W. Yang and G. Yang, Bioorg. Med. Chem., 22, 4784 (2014); https://doi.org/10.1016/j.bmc.2014.06.057
- L. Piazzi, A. Cavalli, F. Colizzi, F. Belluti, M. Bartolini, F. Mancini, M. Recanatini, V. Andrisano and A. Rampa, Bioorg. Med. Chem. Lett., 18, 423 (2008); https://doi.org/10.1016/j.bmcl.2007.09.100
- B. Yuce, O. Danis, A. Ogan, G. Sener, M. Bulut and A. Yarat, Arzneimittelforschung, 59, 129 (2009); https://doi.org/10.1055/s-0031-1296375
- R.S. Keri, K.M. Hosamani, R.V. Shingalapur and M.H. Hugar, Eur. J. Med. Chem., 45, 2597 (2010); https://doi.org/10.1016/j.ejmech.2010.02.048
- N. Ueberschaar, Z. Xu, K. Scherlach, M. Metsa-Ketela, T. Bretschneider, H.M. Dahse, H. Gorls and C. Hertweck, J. Am. Chem. Soc., 135, 17408 (2013); https://doi.org/10.1021/ja4080024
- M.M. Liu, X.Y. Chen, Y.Q. Huang, P. Feng, Y.L. Guo, G. Yang and Y. Chen, J. Med. Chem., 57, 9343 (2014); https://doi.org/10.1021/jm500613m
- S.-C. Tsay, J.R. Hwu, R. Singha, W.-C. Huang, Y.H. Chang, M.-H.Hsu, F. Shieh, C.-C. Lin, K.C. Hwang, J.-C. Horng, E. De Clercq, I.Vliegen and J. Neyts, Eur. J. Med. Chem., 63, 290 (2013); https://doi.org/10.1016/j.ejmech.2013.02.008
- H. Kamiyama, Y. Kubo, H. Sato, N. Yamamoto, T. Fukuda, F. Ishibashi and M. Iwao, Bioorg. Med. Chem., 19, 7541 (2011); https://doi.org/10.1016/j.bmc.2011.10.030
- J.B. Shaik, B.K. Palaka, M. Penumala, K.V. Kotapati, S.R. Devineni, S. Eadlapalli, M.M. Darla, D.R. Ampasala, R. Vadde and G.D. Amooru, Eur. J. Med. Chem., 107, 219 (2016); https://doi.org/10.1016/j.ejmech.2015.10.046
- K.V. Sashidhara, A. Kumar, R.P. Dodda, N.N. Krishna, P. Agarwal, K. Srivastava and S.K. Puri, Bioorg. Med. Chem. Lett., 22, 3926 (2012); https://doi.org/10.1016/j.bmcl.2012.04.100
- R. Pingaew, A. Saekee, P. Mandi, C. Nantasenamat, S. Prachayasittikul, S. Ruchirawat and V. Prachayasittikul, Eur. J. Med. Chem., 85, 65 (2014); https://doi.org/10.1016/j.ejmech.2014.07.087
- I.A. Yule, L.G. Czaplewski, S. Pommier, D.T. Davies, S.K. Narramore and C.W.G. Fishwick, Eur. J. Med. Chem., 86, 31 (2014); https://doi.org/10.1016/j.ejmech.2014.08.025
- H.B. Lad, R.R. Giri and D.I. Brahmbhatt, Chin. Chem. Lett., 24, 227 (2013); https://doi.org/10.1016/j.cclet.2013.01.041
- S.S. Panda, R. Malik, M. Chand and S.C. Jain, Med. Chem. Res., 21, 3750 (2012); https://doi.org/10.1007/s00044-011-9881-0
- K.B. Puttaraju, K. Shivashankar, Chandra, M. Mahendra, V.P. Rasal, P.N. Venkata Vivek, K. Rai and M.B. Chanu, Eur. J. Med. Chem., 69, 316 (2013); https://doi.org/10.1016/j.ejmech.2013.07.015
- R. Nagamallu, B. Srinivasan, M.B. Ningappa and A.K. Kariyappa, Bioorg. Med. Chem. Lett., 26, 690 (2016); https://doi.org/10.1016/j.bmcl.2015.11.038
- K.M. Amin, D.E.A. Rahman and Y.A. Al-Eryani, Bioorg. Med. Chem., 16, 5377 (2008); https://doi.org/10.1016/j.bmc.2008.04.021
- R. Aggarwal, S. Kumar, P. Kaushik, D. Kaushik and G.K. Gupta, Eur. J. Med. Chem., 62, 508 (2013);https://doi.org/10.1016/j.ejmech.2012.11.046
- Y.Q. Hu, S. Zhang, F. Zhao, C. Gao, L.S. Feng, Z.S. Lv, Z. Xu and X. Wu, Eur. J. Med. Chem., 133, 255 (2017); https://doi.org/10.1016/j.ejmech.2017.04.002
- H.P. Lakum, D.R. Shah and K.H. Chikhalia, Lett. Drug Des. Discov., 12, 324341 (2015); https://doi.org/10.2174/1570180811666141009234835
- R. O’Kennedy and R.D. Thornes, Coumarins: Biology, Applications, and Mode of Action, Wiley & Sons: Chichester (1997).
- M. Zabradnik, The Production and Application of Fluorescent Brightening Agents, John Wiley & Sons: New York (1992).
- J.K. Augustine, A. Bombrun, B. Ramappa and C. Boodappa, Tetrahedron Lett., 53, 4422 (2012); https://doi.org/10.1016/j.tetlet.2012.06.037
- M.S. Manhas, S.N. Ganguly, S. Mukherjee, A.K. Jain and A.K. Bose, Tetrahedron Lett., 47, 2423 (2006); https://doi.org/10.1016/j.tetlet.2006.01.147
- J. Li, H. Chen, D. Zhang-Negrerie, Y. Du and K. Zhao, RSC Adv., 3, 4311 (2013); https://doi.org/10.1039/c3ra23188g
- P.T. Kaye, S. Afr. J. Sci., 100, 545 (2004).
- T. Sugino and K. Tanaka, Chem. Lett., 30, 110 (2001); https://doi.org/10.1246/cl.2001.110
- G. Smitha and C.S. Reddy, Synth. Commun., 34, 3997 (2004); https://doi.org/10.1081/SCC-200034821
- L. Wang, J. Xia, H. Tian, C. Qian and Y. Ma, Indian J. Chem., 42B, 2097 (2003).
- A.J. Naddkarni and N.A. Kudav, Indian J. Chem., 20B, 719 (1981).
- S.B. Patil, R.P. Bhat, V.P. Raje and S.D. Samant, Synth. Commun., 36, 525 (2006); https://doi.org/10.1080/00397910500385241
- D.S. Bose, A.P. Rudradas and M.H. Babu, Tetrahedron Lett., 43, 9195 (2002); https://doi.org/10.1016/S0040-4039(02)02266-9
References
N.T. Patil and Y. Yamamoto, Chem. Rev., 108, 3395 (2008); https://doi.org/10.1021/cr050041j
H.A. El-Wahab, M.A. El-Fattah, N.A. El-Khalik, H.S. Nassar and M.M. Abdelall, Prog. Org. Coat., 77, 1506 (2014); https://doi.org/10.1016/j.porgcoat.2014.04.026
Y.K. Al-Majedy, A.A.H. Kadhum, A.A. Al-Amiery and A.B. Mohamad, Sys. Rev. Pharm., 8, 62 (2017); https://doi.org/10.5530/srp.2017.1.11
R.S. Keri, K.M. Hosamani, H.S. Reddy and R.V. Shingalapur, Arch. Pharm., 343, 237 (2010); https://doi.org/10.1002/ardp.200900188
F. Chimenti, B. Bizzarri, A. Bolasco, D. Secci, P. Chimenti, A. Granese, S. Carradori, D. Rivanera, A. Zicari, M.M. Scaltrito and F. Sisto, Bioorg. Med. Chem. Lett., 20, 4922 (2010); https://doi.org/10.1016/j.bmcl.2010.06.048
K.V. Sashidhara, A. Kumar, M. Chatterjee, K.B. Rao, S. Singh, A.K. Verma and G. Palit, Bioorg. Med. Chem. Lett., 21, 1937 (2011); https://doi.org/10.1016/j.bmcl.2011.02.040
I. Kostova, S. Bhatia, P. Grigorov, S. Balkansky, V. S. Parmar, A. K. Prasad and L. Saso, Curr. Med. Chem., 18, 3929 (2001); https://doi.org/10.2174/092986711803414395
S.J. Lee, U.S. Lee, W.J. Kim and S.K. Moon, Mol. Med. Rep., 4, 337 (2011); https://doi.org/10.3892/mmr.2011.420
T.A. De Almeida Barros, L.A.R. De Freitas, J.M.B. Filho, X.P. Nunes, A.M. Giulietti, G.E. De Souza, R.R. Dos Santos, M.B.P. Soares and C.F. Villarreal, J. Pharm. Pharmacol., 62, 205 (2010); https://doi.org/10.1211/jpp.62.02.0008
X.Y. Huang, Z.J. Shan, H.L. Zhai, L. Su and X.Y. Zhang, Chem. Biol. Drug Des., 78, 651 (2011); https://doi.org/10.1111/j.1747-0285.2011.01195.x
J.F. Vasconcelos, M.M. Teixeira, J.M. Barbosa-Filho, M.F. Agra, X.P. Nunes, A.M. Giulietti, R. Ribeiro-Dos-Santos and M.B.P. Soares, Eur. J. Pharmacol., 609, 126 (2009); https://doi.org/10.1016/j.ejphar.2009.03.027
J. Neyts, E.D. Clercq, R. Singha, Y.H. Chang, A.R. Das, S.K. Chakraborty, S.C. Hong, S.-C. Tsay, M.-H. Hsu and J.R. Hwu, J. Med. Chem., 52,1486 (2009); https://doi.org/10.1021/jm801240d
T.O. Olomola, R. Klein, N. Mautsa, Y. Sayed and P.T. Kaye, Bioorg. Med. Chem., 21, 1964 (2013); https://doi.org/10.1016/j.bmc.2013.01.025
A. Manvar, A. Bavishi, A. Radadiya, J. Patel, V. Vora, N. Dodia, K. Rawal and A. Shah, Bioorg. Med. Chem. Lett., 21, 4728 (2011); https://doi.org/10.1016/j.bmcl.2011.06.074
J.-Y. Yeh, M.S. Coumar, J.-T. Horng, H.-Y. Shiao, F.-M. Kuo, H.-L. Lee, I.-C. Chen, C.-W. Chang, W.-F. Tang, S.-N. Tseng, C.-J. Chen, S.-R. Shih, J.T.-A. Hsu, C.-C. Liao, Y.-S. Chao and H.-P. Hsieh, J. Med. Chem., 53, 1519 (2010); https://doi.org/10.1021/jm901570x
Q. Sun, D. Peng, S. Yang, X. Zhu, W. Yang and G. Yang, Bioorg. Med. Chem., 22, 4784 (2014); https://doi.org/10.1016/j.bmc.2014.06.057
L. Piazzi, A. Cavalli, F. Colizzi, F. Belluti, M. Bartolini, F. Mancini, M. Recanatini, V. Andrisano and A. Rampa, Bioorg. Med. Chem. Lett., 18, 423 (2008); https://doi.org/10.1016/j.bmcl.2007.09.100
B. Yuce, O. Danis, A. Ogan, G. Sener, M. Bulut and A. Yarat, Arzneimittelforschung, 59, 129 (2009); https://doi.org/10.1055/s-0031-1296375
R.S. Keri, K.M. Hosamani, R.V. Shingalapur and M.H. Hugar, Eur. J. Med. Chem., 45, 2597 (2010); https://doi.org/10.1016/j.ejmech.2010.02.048
N. Ueberschaar, Z. Xu, K. Scherlach, M. Metsa-Ketela, T. Bretschneider, H.M. Dahse, H. Gorls and C. Hertweck, J. Am. Chem. Soc., 135, 17408 (2013); https://doi.org/10.1021/ja4080024
M.M. Liu, X.Y. Chen, Y.Q. Huang, P. Feng, Y.L. Guo, G. Yang and Y. Chen, J. Med. Chem., 57, 9343 (2014); https://doi.org/10.1021/jm500613m
S.-C. Tsay, J.R. Hwu, R. Singha, W.-C. Huang, Y.H. Chang, M.-H.Hsu, F. Shieh, C.-C. Lin, K.C. Hwang, J.-C. Horng, E. De Clercq, I.Vliegen and J. Neyts, Eur. J. Med. Chem., 63, 290 (2013); https://doi.org/10.1016/j.ejmech.2013.02.008
H. Kamiyama, Y. Kubo, H. Sato, N. Yamamoto, T. Fukuda, F. Ishibashi and M. Iwao, Bioorg. Med. Chem., 19, 7541 (2011); https://doi.org/10.1016/j.bmc.2011.10.030
J.B. Shaik, B.K. Palaka, M. Penumala, K.V. Kotapati, S.R. Devineni, S. Eadlapalli, M.M. Darla, D.R. Ampasala, R. Vadde and G.D. Amooru, Eur. J. Med. Chem., 107, 219 (2016); https://doi.org/10.1016/j.ejmech.2015.10.046
K.V. Sashidhara, A. Kumar, R.P. Dodda, N.N. Krishna, P. Agarwal, K. Srivastava and S.K. Puri, Bioorg. Med. Chem. Lett., 22, 3926 (2012); https://doi.org/10.1016/j.bmcl.2012.04.100
R. Pingaew, A. Saekee, P. Mandi, C. Nantasenamat, S. Prachayasittikul, S. Ruchirawat and V. Prachayasittikul, Eur. J. Med. Chem., 85, 65 (2014); https://doi.org/10.1016/j.ejmech.2014.07.087
I.A. Yule, L.G. Czaplewski, S. Pommier, D.T. Davies, S.K. Narramore and C.W.G. Fishwick, Eur. J. Med. Chem., 86, 31 (2014); https://doi.org/10.1016/j.ejmech.2014.08.025
H.B. Lad, R.R. Giri and D.I. Brahmbhatt, Chin. Chem. Lett., 24, 227 (2013); https://doi.org/10.1016/j.cclet.2013.01.041
S.S. Panda, R. Malik, M. Chand and S.C. Jain, Med. Chem. Res., 21, 3750 (2012); https://doi.org/10.1007/s00044-011-9881-0
K.B. Puttaraju, K. Shivashankar, Chandra, M. Mahendra, V.P. Rasal, P.N. Venkata Vivek, K. Rai and M.B. Chanu, Eur. J. Med. Chem., 69, 316 (2013); https://doi.org/10.1016/j.ejmech.2013.07.015
R. Nagamallu, B. Srinivasan, M.B. Ningappa and A.K. Kariyappa, Bioorg. Med. Chem. Lett., 26, 690 (2016); https://doi.org/10.1016/j.bmcl.2015.11.038
K.M. Amin, D.E.A. Rahman and Y.A. Al-Eryani, Bioorg. Med. Chem., 16, 5377 (2008); https://doi.org/10.1016/j.bmc.2008.04.021
R. Aggarwal, S. Kumar, P. Kaushik, D. Kaushik and G.K. Gupta, Eur. J. Med. Chem., 62, 508 (2013);https://doi.org/10.1016/j.ejmech.2012.11.046
Y.Q. Hu, S. Zhang, F. Zhao, C. Gao, L.S. Feng, Z.S. Lv, Z. Xu and X. Wu, Eur. J. Med. Chem., 133, 255 (2017); https://doi.org/10.1016/j.ejmech.2017.04.002
H.P. Lakum, D.R. Shah and K.H. Chikhalia, Lett. Drug Des. Discov., 12, 324341 (2015); https://doi.org/10.2174/1570180811666141009234835
R. O’Kennedy and R.D. Thornes, Coumarins: Biology, Applications, and Mode of Action, Wiley & Sons: Chichester (1997).
M. Zabradnik, The Production and Application of Fluorescent Brightening Agents, John Wiley & Sons: New York (1992).
J.K. Augustine, A. Bombrun, B. Ramappa and C. Boodappa, Tetrahedron Lett., 53, 4422 (2012); https://doi.org/10.1016/j.tetlet.2012.06.037
M.S. Manhas, S.N. Ganguly, S. Mukherjee, A.K. Jain and A.K. Bose, Tetrahedron Lett., 47, 2423 (2006); https://doi.org/10.1016/j.tetlet.2006.01.147
J. Li, H. Chen, D. Zhang-Negrerie, Y. Du and K. Zhao, RSC Adv., 3, 4311 (2013); https://doi.org/10.1039/c3ra23188g
P.T. Kaye, S. Afr. J. Sci., 100, 545 (2004).
T. Sugino and K. Tanaka, Chem. Lett., 30, 110 (2001); https://doi.org/10.1246/cl.2001.110
G. Smitha and C.S. Reddy, Synth. Commun., 34, 3997 (2004); https://doi.org/10.1081/SCC-200034821
L. Wang, J. Xia, H. Tian, C. Qian and Y. Ma, Indian J. Chem., 42B, 2097 (2003).
A.J. Naddkarni and N.A. Kudav, Indian J. Chem., 20B, 719 (1981).
S.B. Patil, R.P. Bhat, V.P. Raje and S.D. Samant, Synth. Commun., 36, 525 (2006); https://doi.org/10.1080/00397910500385241
D.S. Bose, A.P. Rudradas and M.H. Babu, Tetrahedron Lett., 43, 9195 (2002); https://doi.org/10.1016/S0040-4039(02)02266-9