Abstract
In this study, phosphotungstic acid (H3PW12O40)-supported melamine–terephthalaldehyde Covalent Organic Framework (COF-PTA) has been prepared as a novel solid acid catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine trions under solvent-free conditions. The catalyst was characterized by X-ray diffraction (XRD), thermogravimetric analysis (TGA), Fourier-transform infrared spectroscopy (FT-IR), scanning electron microscope (SEM) and Brunauer–Emmett–Teller (BET) surface area analysis. The advantages of using this ecofriendly protocol include: excellent yield in a shorter time period, inexpensive chemicals without any use of solvents, simple experimental and work-up procedure. The catalyst was readily separated and was recycled for several runs with no significant loss of catalytic property.
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J.B. Zimmerman, P.T. Anastas, H.C. Erythropel, W. Leitner, Science 367, 397 (2020)
V. Polshettiwar, R.S. Varma, Green. Chem. 12, 743 (2010)
J. Li, Z. Yang, G. Hu, J. Zhao, Chem. Eng. J. 388, 124388 (2020)
F. Esmi, V. B. Borugadda, A. K. Dalai, Catal. Today (in press)
M.M. Heravi, S. Sadjadi, J. Iran. Chem. Soc. 6, 1–54 (2009)
C.G.S. Lima, N.M. Moreira, M.W. Paixao, A.G. Correa, Curr. Opin. Green Sustain. Chem. 15, 7 (2019)
B. Changmai, G. Pathak, J.M.H. Anal, L. Rokhum, Mini Rev. Org. Chem. 17, 740 (2020)
M.N. Timofeeva, Appl. Catal. A: Gen. 256, 19 (2003)
J. Li, Z. Yang, S. Li, Q. Jin, J. Zhao, J. Ind. Eng. Chem. 82, 1 (2020)
Q. Zhang, X. Liu, T. Deng, Y. Zhang, P. Ma, Curr. Green. Chem. 7, 267 (2020)
N.A. Khan, B.N. Bhadra, S.H. Jhung, Chem. Eng. J. 334, 2215 (2018)
L. Chen, B. Nohair, D. Zhao, S. Kaliaguine, ChemCatChem 10, 1918 (2018)
R. Ghubayra, C. Nuttall, S. Hodgkiss, M. Craven, E.F. Kozhevnikova, I.V. Kozhevnikov, Appl. Catal., B. 253, 309 (2019)
IVe. Kozhevnikov, K.I. Matveev, Russ. Chem. Rev. 51, 1075 (1982)
N. Lucas, L. Gurrala, A. Athawale, J. Porous Mater. 26, 1335 (2019)
S.W. Li, R.M. Gao, W. Zhang, Y. Zhang, J.S. Zhao, Fuel 221, 1 (2018)
L. Wu, S. An, Y.-F. Song, Engineering 7, 94 (2021)
J. Alcañiz-Monge, B. El Bakkali, G. Trautwein, S. Reinoso, Appl. Catal. B. 224, 194 (2018)
M.D. Morales, A. Infantes-Molina, J.M. Lázaro-Martínez, G.P. Romanelli, L.R. Pizzio, E. Rodríguez-Castellón, Mol. Catal. 485, 110842 (2020)
A. Kurhade, A.K. Dalai, Asia-Pac. J. Chem. Eng. 13, e2249 (2018)
A. Talebian-Kiakalaieh, S. Tarighi, J. Ind. Eng. Chem. 79, 452 (2019)
Q. Zhang, Q. Luo, Y. Wu, R. Yu, J. Cheng, Y. Zhang, RSC. Adv. 11, 33416 (2021)
H.Y. Cheng, T. Wang, Adv. Synth. Catal. 363, 144 (2021)
X. Feng, X. Ding, D. Jiang, Chem. Soc. Rev. 41, 6010 (2012)
C.S. Diercks, O.M. Yaghi, Science 355, eaa11585 (2017)
J.L. Segura, S. Royuela, M.M. Ramos, J. Chem. Soc. Rev. 48, 3903 (2019)
K. Geng, T. He, R. Liu, S. Dalapati, K.T. Tan, Z. Li, S. Tao, Y. Gong, Q. Jiang, D. Jiang, Chem. Rev. 120, 8814 (2020)
S. Kandambeth, K. Dey, R. Banerjee, J. Am. Chem. Soc. 141, 1807 (2018)
J.L. Segura, M.J. Mancheño, F. Zamora, Chem. Soc. Rev. 45, 5635 (2016)
S. Dalapati, S. Jin, J. Gao, Y. Xu, A. Nagai, D. Jiang, J. Am. Chem. Soc. 135, 17310 (2013)
R. Farsi, M.K. Mohammadi, S.J. Saghanezhad, Res. Chem. Intermed. 47, 1161 (2021)
G.M. Ziarani, F. Mohajer, R. Moradi, P. Mofatehnia, Curr. Org. Synth. 16, 953 (2019)
N. Demirbas, A. Demirbas, Curr. Org. Catal. 8, 27 (2021)
F. Masihpour, A. Zare, M. Merajoddin, A. Hasaninejad, J. Chem. Technol. Metall. 54, 23 (2019)
A.R. Kiasat, S. Noorizadeh, M. Ghahremani, S.J. Saghanejad, J. Mol. Struct. 1036, 216 (2013)
A.R. Kiasat, A. Mouradezadegun, S.J. Saghanezhad, J. Serbian Chem. Soc. 78, 469 (2013)
R. Ghahremanzadeh, G.I. Shakibaei, A. Bazgir, Synlett 2008, 1129 (2008)
J.M. Khurana, D. Magoo, Tetrahedron Lett. 50, 7300 (2009)
X. Wang, W.W. Ma, L.Q. Wu, F.L. Yan, J. Chin. Chem. Soc. 57, 1341 (2010)
S.J. Saghanezhad, S. Sayyahi, Res. Chem. Intermed. 43, 2491 (2017)
H.R. Tavakoli, S.M. Moosavi, A. Bazgir, J. Korean. Chem. Soc. 57, 472 (2013)
A. Varghese, A. Nizam, R. Kulkarni, L. George European, J. Chim. 4, 132 (2013)
A. Hasaninejed, M.R. Kazerooni, A. Zare, Catal. Today. 196, 148 (2012)
G. Krishnamurthy, K. Jagannath, J. Chem. Sci. 125, 807 (2013)
W. Scheeren, Bulg. Chem. Commun. 45, 64 (2013)
M. Kidwai, A. Jahan, R. Chauhan, N.K. Mishra, Tetrahedron Lett. 53, 1728 (2012)
M.G. Schwab, B. Fassbender, H.W. Spiess, A. Thomas, X. Feng, K. Mullen, J. Am. Chem. Soc. 131, 7216 (2009)
X. Zhao, N. Yan, RSC Adv. 5, 69955 (2015)
M. Shunmughanathan, P. Puthiaraj, K. Pitchumani, ChemCatChem 7, 666 (2015)
J. Ge, J. Xiao, L. Liu, L. Qiu, X. Jiang, J. Porous Mater. 23, 791 (2016)
Y. Zhuang, H. Shan, Z. Zhang, S. Li, Q. Zhu, Z. Si, S. Yang, Z. Yang, D. Cai, P. Qin, Dyes Pigm. 192, 109421 (2021)
Z. Li, Y. Zhi, Y. Ni, H. Su, Y. Miao, S. Shan, Polymer 217, 123434 (2021)
B. He, W.-C. Li, A.-H. Lu, J. Mater. Chem. A. 3, 13920 (2015)
M. Senthilkumaran, C. Saravanan, P.M. Mareeswaran, Mater. Today: Proc. 40, 5117 (2021)
L. You, K. Xu, G. Ding, X. Shi, J. Li, S. Wang, J. Wang, J. Mol. Liq. 320, 114456 (2020)
M. Pakizeh, P. May, M. Matthias, M. Ulbricht, J. Appl. Polym. Sci. 137, 49595 (2020)
Y. Liu, H. Ou, S. Li, Q. You, H. Liu, G. Liao, D. Wang, J. Environ. Sci. 78, 215 (2019)
K.V. Avramidou, F. Zaccheria, S.A. Karakoulia, K.S. Triantafyllidis, N. Ravasio, Mol. Catal. 439, 60 (2017)
C.S. Maheswari, C. Shanmugapriya, K. Revathy, A. Lalitha, J. Nanostruct. Chem. 7, 283 (2017)
N. Iravani, M. Keshavarz, A. Parhami, Res. Chem. Intermed. 45, 5045 (2019)
J. Albadi, M. Jalali, A. Momeni, Res. Chem. Intermed. 44, 2395 (2018)
M. Esmaeilpour, J. Javidi, F.N. Dodeji, S. Zahmatkesh, Res. Chem. Intermed. 47, 2629 (2021)
F. Arian, M. Keshavarz, H. Sanaeishoar, N. Hasanzadeh, J. Mol. Struct. 1229, 129599 (2021)
S. Karhale, V. Helavi, S.N. Appl, Sci. 2, 1227 (2020)
A.R. Kiasat, J. Davarpanah, J. Mol. Catal. A: Chem. 373, 46 (2013)
G. Sabitha, C. Srinivas, A. Raghavendar, J.S. Yadav, Helv. Chim. Acta. 93, 1375 (2010)
R. Tayebee, M.F. Abdizadeh, B. Maleki, E. Shahri, J. Mol. Liq. 241, 447 (2017)
B. Atashkar, A. Rostami, H. Gholami, B. Tahmasbi, Res. Chem. Intermed. 41, 3675 (2015)
R. Tayebee, M. Jomei, B. Maleki, M.K. Razi, H. Veisi, M. Bakherad, J. Mol. Liq. 206, 119 (2015)
A. Mulik, D. Chandam, P. Patil, D. Patil, S. Jagdale, S. Sankpal, M. Deshmukh, J. Heterocycl. Chem. 52, 931 (2015)
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The authors disclosed receipt of financial support for the research, from Vice-Chancellor for Research Affairs of Ahvaz Jundishapur University of Medical Sciences (grant number: N-0006).
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Seyyed Jafar Saghanezhad contributed to conceptualization, methodology, validation, writing and editing the manuscript. Luigi Vaccaro contributed to methodology, validation, editing and supervision. Amanollah Zarei Ahmady contributed to conceptualization, methodology, validation, supervision, editing the final draft. Razieh Farsi contributed to experimental work assistance, writing original draft.
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Saghanezhad, S.J., Vaccaro, L., Zarei Ahmady, A. et al. Phosphotungstic acid-supported melamine–terephthalaldehyde covalent organic framework as a novel and reusable nanostructured catalyst in three-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives. Res Chem Intermed 48, 3851–3865 (2022). https://doi.org/10.1007/s11164-022-04776-9
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DOI: https://doi.org/10.1007/s11164-022-04776-9