Abstract
In this research, an acid-modified biochar catalyst was developed for the synthesis of perimidine derivatives, utilizing the bark of the Ficus religiosa (peepal) tree as a carbon source for the biochar formation. The catalyst was produced through pyrolysis at 550 °C followed by treatment with chlorosulfonic acid. The synthesized catalyst, biochar sulfonic acid (BCSA) was characterized by fourier-transform infrared spectroscopy, X-ray diffraction, scanning electron microscope, and energy-disperse X-ray spectroscopy. A diverse collection of perimidine derivatives was prepared in a short reaction time (< 1 h) with high to excellent yields (72–95%) by the cyclocondensation reaction of 1,8-diaminonaphthalene with a variety of carbonyl compounds (ketones and aldehydes). Our newly developed protocol showcases a range of eco-friendly attributes, including metal-free synthesis, one-pot single-step operation, catalyst recyclability, a broad substrate scope, and the capability for gram-scale synthesis. This work marks a significant advancement in sustainable catalysis and green chemical processes.
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P. Arora, V. Arora, H. Lamba, D. Wadhwa, Int. J. Pharm. Sci. Res. 3, 2947 (2012)
N. Sahiba, S. Agarwal, Top. Curr. Chem. 378, 1 (2020)
T.A. Farghaly, M.A. Abdallah, Z.A. Muhammad, Res. Chem. Intermed. 41, 3937 (2015)
H.-J. Zhang, X.-Z. Wang, Q. Cao, G.-H. Gong, Z.-S. Quan, Bioorganic Med Chem. Lett. 27, 4409 (2017)
K. Arya, A. Dandia, Lett. Org. Chem. 4, 378 (2007)
M. Brana, M. Garrido, M.L. Rodriguez, M. Morcillo, Y. Alvarez, Y. Valladares, G. Klebe, Eur. J. Med. Chem. 25, 209 (1990)
V.A. Kharlanov, J. Photochem. Photobiol. A: Chem. 122, 191 (1999)
M. Azam, I. Warad, S.I. Al-Resayes, N. Alzaqri, M.R. Khan, R. Pallepogu, S. Dwivedi, J. Musarrat, M. Shakir, J. Mol. Struct. 1047, 48 (2013)
R.F. Malherbe, U.S. Patent. US 4, 389, 321, 6(Google Patents, 1983)
S.Y. Hsueh, K.W. Cheng, C.C. Lai, S.H. Chiu, Angew. Chem. Int. Ed. 47, 4436 (2008)
B. Alıcı, İ Özdemir, K. Karaaslan, E. Çetinkaya, B. Çetinkaya, J Mol Catal A Chem. 231, 261 (2005)
S. Ernst, J. Mistol, B. Senns, L. Hennig, D. Keil, Dyes Pigm. 154, 216 (2018)
M. Azam, I. Warad, S. Al-Resayes, M. Zahin, I. Ahmad, M. Shakir, Z. Anorg. Allg. Chem. 638, 881 (2012)
F.A. Bassyouni, S.M. Abu-Bakr, K.H. Hegab, W. El-Eraky, A.A. El Beih, M.E.A. Rehim, Res. Chem. Intermed. 38, 1527 (2012)
A. Mobinikhaledi, M. Bodaghi Fard, F. Sasani, M. Amrollahi, Bulg. Chem. Commun. 45, 353 (2013)
N. Nagasundaram, C. Govindhan, S. Sumitha, N. Sedhu, K. Raguvaran, S. Santhosh, A. Lalitha, J. Mol. Struct. 1248, 131437 (2022)
W. Wasulko, A.C. Noble, F.D. Popp, J. Med. Chem. 9, 599 (1966)
W.-L. Wang, D.-L. Yang, L.-X. Gao, C.-L. Tang, W.-P. Ma, H.-H. Ye, S.-Q. Zhang, Y.-N. Zhao, H.-J. Xu, Z. Hu, Molecules 19, 102 (2013)
V. Paragamian, M. Baker, B. Puma, J. Reale Jr., J. Heterocycl. Chem. 5, 591 (1968)
N.A. Harry, S. Radhika, M. Neetha, G. Anilkumar, J. Heterocycl. Chem. 57, 375 (2020)
J. Zhang, S.L. Zhang, J.M. Zhang, Chin. Chem. Lett. 18, 1057 (2007)
Z. Yasaei, P. Mirzaei, A. Bazgir, C. R. Chim. 13, 1308 (2010)
S.L. Zhang, J.M. Zhang, Chinese J. Chem. 26, 185 (2008)
J. Zhang, S. Zhang, Synth. Commun. 37, 2615 (2007)
M.A. Bodaghifard, N. Ahadi, Iran. J. Catal. 6, 377 (2016)
P.B. Shelke, S.N. Mali, H.K. Chaudhari, A.P. Pratap, J. Heterocycl. Chem. 56, 3048 (2019)
S. Khopkar, G. Shankarling, J. Chem. Sci. 132, 1 (2020)
N.A. Harry, T. Shilpa, S.M. Ujwaldev, G. Anilkumar, J. Heterocycl. Chem. 58, 375 (2021)
S.B. Phadtare, R. Vijayraghavan, G.S. Shankarling, D.R. MacFarlane, Aust. J. Chem. 65, 86 (2011)
G.S. Prakash, F. Paknia, A. Narayan, T. Mathew, G.A. Olah, J. Fluor. Chem. 152, 99 (2013)
T. Xie, K.R. Reddy, C. Wang, E. Yargicoglu, K. Spokas, Crit. Rev. Environ. Sci. Technol. 45, 939 (2015)
S.K. Das, G.K. Ghosh, R. Avasthe, Biomass Convers. Biorefin. 13, 1 (2020)
W.-J. Liu, H. Jiang, H.-Q. Yu, Energy Environ. Sci. 12, 1751 (2019)
R. Shan, J. Han, J. Gu, H. Yuan, B. Luo, Y. Chen, Resour. Conserv. Recycl. 162, 105036 (2020)
S.S. Karbasaki, G. Bagherzade, B. Maleki, M. Ghani, Org. Prep. Proced. Int. 53, 498 (2021)
S.S. Karbasaki, G. Bagherzade, B. Maleki, M. Ghani, J. Taiwan Inst. Chem. Eng. 118, 342–354 (2021)
H. Alinezhad, M. Tarahomi, B. Maleki, A. Amiri, Appl. Organomet. Chem. 33, e4661 (2019)
B. Maleki, O. Reiser, E. Esmaeilnezhad, H.J. Choi, Polyhedron 162, 129 (2019)
L.-N. Dong, S.-Z. Zhang, W.-L. Zhang, Y. Dong, L.-P. Mo, Z.-H. Zhang, Res. Chem. Intermed. 48, 1249 (2022)
C. Peiris, O. Nayanathara, C.M. Navarathna, Y. Jayawardhana, S. Nawalage, G. Burk, A.G. Karunanayake, S.B. Madduri, M. Vithanage, M. Kaumal, RSC Adv. 9, 17612 (2019)
C. Zhao, P. Lv, L. Yang, S. Xing, W. Luo, Z. Wang, Energy Convers. Manag. 160, 477 (2018)
S. Dechakhumwat, P. Hongmanorom, C. Thunyaratchatanon, S.M. Smith, S. Boonyuen, A. Luengnaruemitchai, Renew. Energ. 148, 897 (2020)
A.S. Yusuff, K.A. Thompson-Yusuff, J. Porwal, RSC Adv. 12, 10237 (2022)
M.A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. Soc. 14, 365 (2017)
V.V. Patil, G.S. Shankarling, Catal. Commun. 57, 138 (2014)
H. Alinezhad, M. Zare, J. Chil. Chem. Soc. 58, 1840 (2013)
A. Lapkin, D. Constable, Green chemistry metrics: measuring and monitoring sustainable processes (Wiley, Hoboken, 2008), p.91
J. Soni, A. Sethiya, N. Sahiba, D. Joshi, S. Agarwal, Polycycl. Aromat. Compd. 43, 674 (2023)
K.M. Salih, D. Ameen, A.N. Hamad, A.R. Ganjo, S. Muhammed, Zanco J Med. Sci. 24, 68 (2020)
N. Chakraborty, S. Banik, A. Chakraborty, S.K. Bhattacharya, S. Das, J. Photochem. Photobiol. A: Chem. 377, 236 (2019)
I. Yavari, H. Mostafavi, D. Tahmassebi, R. Hekmat-Shoar, Monatsh. Chem. 128, 675 (1997)
Acknowledgements
The authors are thankful to Department of Chemistry, MLSU, Udaipur for providing research facilities, and Department of Physics, MLSU, Udaipur, and PU, Chandigarh for IR, XRD, SEM, and EDX studies respectively. P. Teli wish to acknowledge CSIR, India (09/172(0099)2019-EMR-I) for senior research fellowship as financially support. S. Agarwal sincerely acknowledges Ministry of Education, SPD-RUSA Rajasthan for providing NMR facility under RUSA 2.0, Research, and Innovation project (F/RUSA/GEN/MLSU/2020).
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S.T. performed the experiment and wrote the main manuscript text, S.S., P.T., and N.S. helped in data interpretation and reviewing of the manuscript, and S. A. for writing, revising, overall reviewing of the manuscript and supervision.
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Teli, S., Soni, S., Teli, P. et al. Unlocking the potential of Ficus religiosa tree bark-derived biochar sulfonic acid: a journey from synthesis and characterization to its astonishing catalytic role in green synthesis of perimidines. Res Chem Intermed 50, 1475–1495 (2024). https://doi.org/10.1007/s11164-023-05199-w
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DOI: https://doi.org/10.1007/s11164-023-05199-w