Abstract
In the present investigation, we have developed an efficient and eco-friendly protocol for the synthesis of pyrazole anchored 1,4-dihydropyridine analogs using pumice-based sulfonic acid (pumice@SO3H) as a recyclable solid acid catalyst under simple stirring at room temperature. The present protocol proceeded smoothly with 1,3-diaryl pyrazole-4-carbaldehydes, ethyl acetoacetate, and NH4OAc in ethanol as a solvent with excellent yield. The pumice-based sulfonic acid catalyst is easily prepared from naturally occurring pumice by simple agitation with chlorosulfonic acid. The key features of this catalyst are its heterogeneous nature, high porosity, non-corrosive and non-toxic nature, recyclability, stable and highly efficient at room temperature. The application of this catalyst makes the protocol more environmentally benign.
Graphical abstract
Similar content being viewed by others
References
A. Maleki, S. Gharibi, K. Valadi, R. Taheri-Ledari, J. Phys. Chem. Solids. 142, 109443 (2020)
A. Tambe, A. Gadhave, A. Pathare, G. Shirole, Sustain. Chem. Pharm. 22, 100485 (2021)
K. Valadi, S. Gharibi, R.T. Ledari, A. Maleki, Solid State Sci. 101, 106141 (2020)
A. Alver, M. Karaarslan, A. Kilic, Environ. Technol. 37, 2040 (2016)
G.S. Kumar, Y. Poornachandra, S.K. Gunda, K.R. Reddy, J. Mohmed, K. Shaik, C.G. Kumar, B. Narsaiah, Bioorg. Med. Chem. Lett. 28, 2328 (2018)
E.R. Kotb, H.S. Abbas, E.M. Flefel, H.H. Sayed, N.A.M. Abdelwahed, J. Heterocycl. Chem. 52, 1531 (2015)
P. Swiatek, M. Strzelecka, R. Urniaz, K. Gebczak, T. Gebarowski, K. Gasiorowski, W. Malinka, Bioorg. Med. Chem. 25, 316 (2017)
D. Anand, P.K. Yadav, O.P. Patel, N. Parmar, R.K. Maurya, P. Vishwakarma, K.S. Raju, I. Taneja, M. Wahajuddin, S. Kar, P.P. Yadav, J. Med. Chem. 60, 1041 (2017)
N.H. Gokhale, S.B. Padhye, D.C. Billington, D.L. Rathbone, S.L. Croft, H.D. Kendrick, C.E. Anson, A.K. Powell, Inorg. Chim. Acta. 49, 23 (2003)
E.H. El-Sayed, A.A. Fadda, J. Heterocycl. Chem. 55, 2251 (2018)
E. Baydar, M.G. Gunduz, V.S. Krishna, R. Simsek, D. Sriram, S.O. Yıldırım, R.J. Butcher, C. Safak, Res. Chem. Intermed. 43, 7471 (2017)
R. Ghorbani-Vaghei, S.M. Malaekehpoor, P. Hasanein, R. Karamyan, M. Asadbegy, Res. Chem. Intermed. 42, 4715 (2016)
Q. Tang, Y. Duan, L. Wang, M. Wang, Y. Ouyang, C. Wang, H. Mei, S. Tang, Y. Xiong, P. Zheng, P. Gong, W. Zhu, Eur. J. Med. Chem. 143, 266 (2018)
M.A. Abdelrahman, I. Salama, M.S. Gomaa, M.M. Elaasser, M.M. Abdel-Aziz, D.H. Soliman, Eur. J. Med. Chem. 138, 698 (2017)
H.A.S. Abbas, W.A. El Sayed, N.M. Fathy, Eur. J. Med. Chem. 45, 973 (2010)
N.N. El-Sayed, M.A. Abdelaziz, W.W. Wardakhan, R.M. Mohareb, Steroids 107, 98 (2016)
T. Li, J. Zhang, J. Pan, Z. Wu, D. Hu, B. Song, Eur. J. Med. Chem. 125, 657 (2017)
A.K. Kumari, V.H. Reddy, G.M. Reddy, Y.V.R. Reddy, S. Leelavathi, J. Heterocycl. Chem 56, 1661 (2019)
G.B. Dharma Rao, J. Heterocycl. Chem. 52, 2556 (2018)
M.R. Khumalo, S.N. Maddila, S. Maddila, S.B. Jonnalagadda, Chemistry Select 4, 12503 (2019)
M. Abaszadeh, M. Seifi, A. Asadipour, Res. Chem. Intermed. 41, 5229 (2015)
S.J. Ji, Z.Q. Jiang, J. Lu, T.P. Loa, Synlett 5, 831 (2004)
N. Ahadi, A. Mobinikhaledi, M.A. Bodaghifard, Appl. Organomet. Chem. 34, e5822 (2020)
H. Alinezhad, S.M. Tavakkoli, Res. Chem. Intermed. 41, 5931 (2015)
R.A. Mekheimer, A.A. Hameed, K.U. Sadek, Green Chem. 10, 592 (2008)
J.F. Zhou, Y.Z. Song, J.S. Lv, G.X. Gong, S. Tu, Synth. Commun. 39, 8 (2009)
R. Farsi, M.K. Mohammadi, S.J. Saghanezhad, Res. Chem. Intermed. 47, 1161 (2020)
S.S. Mansoor, K. Aswin, K. Logaiya, P.N. Sudhan, S. Malik, Res. Chem. Intermed. 40, 2 (2014)
S. Zhaleh, N. Hazeri, M.R. Faghihi, M.T. Maghsoodlou, Res. Chem. Intermed. 42, 8089 (2016)
S.N. Maddila, S. Maddila, K.K. Gangu, W.E. van Zyl, S.B. Jonnalagadda, J. Fluor. Chem. 195, 79 (2017)
T. Akbarpoor, A. Khazaei, J.Y. Seyf, N. Sarmasti, M.M. Gilan, Res. Chem. Intermed. 46, 1539 (2020)
Z. Shahamat, F. Nemati, A. Elhampour, Res. Chem. Intermed. 44, 6649 (2018)
A. Shaabani, S. Shaabani, M. Seyyedhamzeh, M.H. Sangachin, F. Hajishaabanha, Res. Chem. Intermed. 42, 7247 (2016)
S.K. Singh, K.N. Singh, J. Heterocycl. Chem. 47, 194 (2010)
A.G. Sathicq, G.P. Romanelli, A. Ponzinibbio, G.T. Baronetti, H.J. Thomas, Lett. Org. Chem. 7, 511 (2010)
A. Kumar, R.A. Maurya, Tetrahedron 63, 1946 (2007)
A. Maleki, M. Kamalzare, M. Aghaei, J. Nanostruct. Chem. 5, 95 (2015)
M.G. Dehbalaei, N. Foroughifar, A. Khajeh-Amiri, H. Pasdar, J. Chin. Chem. Soc. 65, 1356 (2018)
C.G. Evans, J.E. Gestwicki, Org. Lett. 11, 2957 (2009)
A. Khojastehnezhad, F. Moeinpour, A. Davoodnia, Chin. Chem. Lett. 22, 807 (2011)
A. Kumar, R.A. Maurya, Synlett 6, 883 (2008)
S. Ko, C.F. Yao, Tetrahedron 62, 7293 (2006)
S. Wu, J. Wang, W. Zhang, X. Ren, Catal. Lett. 125, 3 (2008)
S.S. Mansoor, K. Aswin, K. Logaiya, P.N. Sudhan, S. Malik, Res. Chem. Intermed. 40, 357 (2012)
P. Suman, H.C. Lokman, P. Tasneem, Synth. Commun. 43, 986 (2013)
G.D. Shirole, R.A. Mokal, S.N. Shelke, Lett. Org. Chem. 14, 548 (2017)
R. Murugan, K. Ramamurthy, S. Sundarrajan, S. Ramakrishna, Tetrahedron 68, 7196 (2012)
P. Kumara, K. Hussain, A. Kumar, Curr. Chem. Lett. 3, 75 (2014)
K.A. More, N.V. Gandhare, P.S. Ali, N.B. Pathan, K.M. Al-Mousa, Curr. Res. Green Sustain. Chem. 4, 100108 (2021)
J. Li, J. Qiu, H. Li, G. Zhang, Chin. J. Chem. 29, 511 (2011)
G.D. Shirole, A.S. Tambe, S.N. Shelke, Indian J. Chem. Sec B. 59B, 459 (2020)
G.D. Shirole, V.A. Kadnor, A.S. Tambe, S.N. Shelke, Res. Chem. Intermed. 43, 1089 (2017)
G.D. Shirole, S. Bhalekar, S.N. Shelke, Indian J. Chem. Sec B. 57B, 1430 (2018)
V. Kadnor, A. Tambe, G. Shirole, Heterocycl. Lett. 10, 407 (2020)
G. Shirole, V. Kadnor, S. Gaikwad, N. Kshirsagar, G. Mhaske, S. Shelke, Res. Chem. Intermed. 42, 4785 (2016)
V.A. Chornous, M.K. Bratenko, M.V. Vovk, Chem. Heterocycl. Compd. 42, 1242 (2006)
Acknowledgements
The authors are grateful to the Principal of ASC College, Rahata for providing the necessary facilities and SAIF, University of Punjab, Chandigarh for providing the spectral characterization.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Tambe, A., Sadaphal, G., Dhawale, R. et al. Pumice-based sulfonic acid: a sustainable and recyclable acidic catalyst for one-pot synthesis of pyrazole anchored 1,4-dihydropyridine derivatives at room temperature. Res Chem Intermed 48, 1273–1286 (2022). https://doi.org/10.1007/s11164-021-04649-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-021-04649-7