Synthesis of Pyrazolo-[4́,3́:5,6]pyrido[2,3-d]pyrimidine-diones Catalyzed by a Nano-sized Surface-Grafted Neodymium Complex of the Tungstosilicate via Multicomponent Reaction
Mansoureh Daraie
Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran
Search for more papers by this authorCorresponding Author
Majid M. Heravi
Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran
Correspondence
Majid M. Heravi, Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran. Email: [email protected]; [email protected]
Masoud Mirzaei, Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran. Email: [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Masoud Mirzaei
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran
Correspondence
Majid M. Heravi, Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran. Email: [email protected]; [email protected]
Masoud Mirzaei, Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran. Email: [email protected]; [email protected]
Search for more papers by this authorNahid Lotfian
Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran
Search for more papers by this authorMansoureh Daraie
Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran
Search for more papers by this authorCorresponding Author
Majid M. Heravi
Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran
Correspondence
Majid M. Heravi, Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran. Email: [email protected]; [email protected]
Masoud Mirzaei, Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran. Email: [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Masoud Mirzaei
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran
Correspondence
Majid M. Heravi, Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran. Email: [email protected]; [email protected]
Masoud Mirzaei, Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran. Email: [email protected]; [email protected]
Search for more papers by this authorNahid Lotfian
Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran
Search for more papers by this authorAbstract
An inorganic–organic hybrid based on lanthanide clusters and Keggin type polyoxometalates (POMs) (Na[Nd (pydc-OH)(H2O)4]3}[SiW12O40]) was used the first time as trinuclear catalyst for one pot synthesis of pyrazolo[4́́,3́:5,6]pyrido[2,3-d]pyrimidine-diones, via two different four and five-component reactions involving hydrazine hydrate, ethyl acetoacetate, aryl aldehydes, and 6-amino-1,3-dimethyl uracil or barbituric acid with ammonium acetate as alternative materials in green condition. To evaluate potential application of the as-made hybrid in adsorption and separation processes, nitrogen adsorption was performed at 77 K through simulation study. The hybrid catalyst was further characterized via powder X-ray diffraction (PXRD) at room temperature which indicated the good phase purity of the catalyst. The results show that the catalytic activity of the hybrid catalyst has increased relative to each parent component due to the special interaction between Keggin anions and pydc-OH ligands.
Supporting Information
| Filename | Description |
|---|---|
| aoc5058-sup-0001-Supporting information.docxWord 2007 document , 691.3 KB |
FIGURE S1 IR spectrum of 3,6,8-Trimethyl-4-phenyl-8,9-dihydro-1H-pyrazolo[4′,3′:5,6] pyrido[2,3-d]pyrimidine-5,7-(4H,6H)-dione FIGURE S2 1HNMR spectrum of 3,6,8-Trimethyl-4-phenyl-8,9-dihydro-1H-pyrazolo[4′,3′:5,6] pyrido[2,3-d]pyrimidine-5,7-(4H,6H)-dione FIGURE S3 IR spectrum of 4-(4-Fluorophenyl)-3,6,8-trimethyl-8,9-dihydro-1H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-5,7(4H,6H)-dione FIGURE S4 1HNMR spectrum of 4-(4-Fluorophenyl)-3,6,8-trimethyl-8,9-dihydro-1H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-5,7(4H,6H)-dione FIGURE S5 13CNMR spectrum of 4-(4-Fluorophenyl)-3,6,8-trimethyl-8,9-dihydro-1H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-5,7(4H,6H)-dione FIGURE S6 IR spectrum of 3,6,8-Trimethyl-1,4-diphenyl-8,9-dihydro-1H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-5,7(4H,6H)-dione FIGURE S7 1HNMR spectrum of 3,6,8-Trimethyl-1,4-diphenyl-8,9-dihydro-1H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-5,7(4H,6H)-dione FIGURE S8 IR spectrum of 4-(4-Chlorophenyl)-3,6,8-trimethyl-8,9-dihydro-1H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-5,7(4H,6H)-dione FIGURE S9 1HNMR spectrum of 4-(4-Chlorophenyl)-3,6,8-trimethyl-8,9-dihydro-1H-pyrazolo [4′,3′:5,6]pyrido[2,3-d]pyrimidine-5,7(4H,6H)-dione FIGURE S10 13CNMR spectrum of 4-(4-Chlorophenyl)-3,6,8-trimethyl-8,9-dihydro-1H-pyrazolo [4′,3′:5,6]pyrido[2,3-d]pyrimidine-5,7(4H,6H)-dione |
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REFERENCES
- 1R. K. Arafa, M. S. Nour, N. A. El-Sayed, Eur. J. Med. Chem. 2013, 69, 498.
- 2L. Wei, S. V. Malhotra, Med. Chem. Comm. 2012, 3, 1250.
- 3M. R. Mahmoud, A. K. El-Ziaty, M. F. Ismail, S. A. Shiba, Eur. J. Chem. 2011, 2, 347.
- 4A. M. El-Agrody, F. M. Ali, F. A. Eid, M. A. El-Nassag, G. El-Sherbeny, A. H. Bedair, Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 839.
- 5N. Fujiwara, T. Nakajima, Y. Ueda, H. Fujita, H. Kawakami, Bioorg. Med. Chem. 2008, 16, 9804.
- 6A. E. Amr, N. M. Sabry, M. M. Abdulla, Monatsh. Chem. 2007, 138, 699.
- 7L. K. Adsul, B. P. Bandgar, H. V. Chavan, S. S. Jalde, V. D. Dhakane, A. L. Shirfule, J. Enzyme. Inhibit. Med. Chem. 2013, 28, 1316.
- 8L. Ballell, R. A. Field, G. A. Chung, R. J. Young, Bioorg. Med. Chem. Lett. 2007, 17, 1736.
- 9D. W. Fry, M. A. Becker, R. L. Switzer, Mol. Pharmaceutics 1995, 47, 810.
- 10M. G. Gebauer, C. McKinlay, J. E. Gready, Eur. J. Med. Chem. 2003, 38, 719.
- 11G. W. Rewcastle, A. J. Bridges, D. W. Fry, J. R. Rubin, W. A. Denny, J. Med. Chem. 1997, 40, 1820.
- 12M. Bakavoli, M. M. Heravi, H. Germaninajad, M. Rahimizadeh, M. Ghassemzadeh, Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 381.
- 13A. Shaabani, M. Seyyedhamzeh, A. Maleki, M. Behnam, F. Rezazadeh, Tetrahedron Lett. 2009, 50, 2911.
- 14S. P. Satasia, P. N. Kalaria, D. K. Raval, Org. Biomol. Chem. 2014, 12, 1751.
- 15M. T. Pope, Heteropoly and isopoly oxometalates, Springer-Verlag 1983.
10.1007/978-3-662-12004-0 Google Scholar
- 16N. Mizuno, M. Misono, Chem. Rev. 1998, 98, 199.
- 17I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171.
- 18M. M. Heravi, S. Sadjadi, J. Iran. Chem. Soc. 2009, 6, 1.
- 19S. S. Wang, G. Y. Yang, Chem. Rev. 2015, 115, 4893.
- 20I. V. Kozhevnikov, J. Mol. Catal. A: Chem. 2007, 262, 86.
- 21M. M. Heravi, M. Mirzaei, S. Y. Beheshtiha, V. Zadsirjan, F. M. Ameli, M. Bazargan, App. Organometal. Chem. 2018, 32, e4479.
- 22R. Yu, X. F. Kuang, X. Y. Wu, C. Z. Lu, J. P. Donahue, Coord. Chem. Rev. 2009, 253, 2872.
- 23M. Mirzaei, H. Eshtiagh-Hosseini, M. Alipour, A. Frontera, Coord. Chem. Rev. 2014, 275, 1.
- 24S. Taleghani, M. Mirzaei, H. Eshtiagh-Hosseini, A. Frontera, Coord. Chem. Rev. 2016, 309, 84.
- 25N. Lotfian, M. M. Heravi, M. Mirzaei, B. Heidari, Appl. Organometal. Chem. 2019, 33, e4808.
- 26M. Wei, C. He, Q. Sun, Q. Meng, C. Duan, Inorg. Chem. 2007, 46, 5957.
- 27C. M. Granadeiro, R. A. Ferreira, P. C. Soares-Santos, L. D. Carlos, H. I. Nogueira, Eur. J. Inorg. Chem. 2009, 2009, 5088.
- 28H. An, Z. Han, T. Xu, Inorg. Chem. 2010, 49, 11403.
- 29W. F. Zhao, C. Zou, L. X. Shi, J. C. Yu, G. D. Qian, C. D. Wu, Dalton Trans. 2012, 41, 10091.
- 30M. M. Heravi, T. Alishiri, Adv. Heterocycl. Chem. 2014, 113, 1.
- 31M. M. Heravi, B. Talaei, Adv. Heterocycl. Chem. 2014, 113, 143.
- 32M. M. Heravi, V. F. Vavsari, Adv. Heterocycl. Chem. 2015, 114, 77.
- 33M. M. Heravi, S. Khaghaninejad, M. Mostofi, Adv. Heterocycl. Chem. 2014, 112, 1.
- 34M. M. Heravi, B. Baghernejad, H. A. Oskooie, R. Hekmatshoar, Tetrahedron Lett. 2008, 49, 6101.
- 35M. M. Heravi, L. Ranjbar, F. Derikvand, B. Alimadadi, H. A. Oskooie, F. F. Bamoharram, Mol. Diversity 2008, 12, 181.
- 36M. M. Heravi, F. Derikvand, M. Haghighi, Monatsh. Chem. 2008, 139, 31.
- 37M. M. Heravi, G. Rajabzadeh, F. F. Bamoharram, N. Seifi, J. Mol. Catal. A: Chem. 2006, 256, 238.
- 38S. Sadjadi, M. M. Heravi, M. Daraie, Res. Chem. Intermed. 2017, 43, 2201.
- 39M. M. Heravi, S. Sadjadi, N. M. Haj, H. A. Oskooie, F. F. Bamoharram, Catal. Commun. 2009, 10, 1643.
- 40S. Sadjadi, M. M. Heravi, M. Daraie, J. Mol. Liquids. 2017, 231, 98.
- 41M. Mirzaei, H. Eshtiagh-Hosseini, N. Lotfian, A. Salimi, A. Bauzá, R. Van Deun, R. Decadt, A. F. Barceló-Oliver, Dalton Trans. 2014, 43, 1906.
- 42M. Alipour, O. Akintola, A. Buchholz, M. Mirzaei, H. Eshtiagh-Hosseini, H. Görls, W. Plass, Eur. J. Inorg. Chem. 2016, 2016, 5356.
- 43A. Najafi, M. Mirzaei, J. T. Mague, CrystEngComm 2016, 18, 6724.
- 44M. Arab. Fashapoyeh, M. Mirzaei, H. Eshtiagh-Hosseini, A. Rajagopal, M. Lechner, R. Liu, C. Streb, Chem. Commun. 2018, 54, 10427.
- 45N. Lotfian, M. Mirzaei, H. Eshtiagh-Hosseini, M. Löffler, M. Korabik, A. Salimi, Eur. J. Inorg. Chem. 2014, 2014, 5908.
- 46W. L. Xie, Z. J. C. Z. Y. Li, W. Q. Tao, Computation 2016, 4, 18.
- 47K. S. Walton, R. Q. Snurr, J. Am. Chem. Soc. 2007, 129, 8552.
- 48(a)A. Hassanpoor, M. Mirzaei, M. Niknam Shahrak, A. M. Majcher, Dalton Trans. 2018, 47, 13849. (b)B. Ramezanpour, M. Mirzaei, V. Jodaian, M. Niknam Shahrak, A. Frontera, E. Molins, Inorg. Chim. Acta 2019, 484, 264.
- 49M. Daraie, M. M. Heravi, ARKIVOC 2016, 4, 328.
- 50M. M. Heravi, M. Daraie, Molecules 2016, 21, 441.
