Tungstate sulfuric acid: a highly efficient catalyst in solvent-free multi-component reactions

Document Type : Research Article

Authors
1 Department of chemistry, Yasouj University, Yasouj Iran
2 Department of chemistry, Yasouj University, Yasouj , Iran
3 Department of chemistry, Yasouj University, Iran
4 Department of Applied Chemistry, Yasouj University,
5 Faculty of Chemistry, , Isfahan University of Technology, Isfahan, Iran
amnc.2022.10.40.4
Abstract
The green synthesis of 2H-indazolo[2,1-b] phthalazine-triones, as a group of phthalazine derivatives, and triazolo[1,2-a]indazole-triones, as a group of urazole derivatives by employing three-component condensation of aldehydes and dimedone with a phthalhydrazide or N-phenylurazole is an actively growing area in organic synthesis. A simple, ecofriendly method based on using tungstate sulfuric acid (TSA), as a highly efficient catalyst, is proposed for the one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-trione and triazolo[1,2-a]indazole-trione derivatives by the three-component condensation reaction of 4-phenylurazole or phthalhydrazide, dimedone, and various aromatic aldehydes under solvent-free conditions in excellent yields and very short reaction times. It was found that low amount of the catalysts is optimized amount to achieve desired products in short times (5-10 min) with high isolated yields (90-95%). Some superiorities of the introduced catalysts are their novelty, simple separation and their reusability up to six repeated runs without significant catalytic deactivation. principals such as green conditions, straightforward processes without any byproduct, no need for expensive, time consuming and tedious extraction or purification techniques which could make this catalyst favorable and superior catalysts for organic transformations.
Keywords

[1] C.V. Karunaratne, R.G. Sarkisian, J. Reeves, Y. Deng, K.A. Wheeler, H. Wang, Multicomponent reaction through cooperative trio catalysis incorporating enamine, Brønsted acid and metal Lewis acid catalysis: a concise route to access chromans, Org. Biomol. Chem., 15, 23(2017) 4933-4936.
[2] A. Hasaninejed, M.R. Kazerooni, A. Zare, Room-temperature, catalyst-free, one-pot pseudo-five-component synthesis of 4,4-(arylmethylene) bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s under ultrasonic irradiation, ACS Sustain. Chem. Eng., 1, 6(2013) 679-684.
[3] F. Masihpour, A. Zare, M. Merajoddin, A. Hasaninejad, Highly effectual protocol for the production of triazolo[1,2-a] indazole-triones and 2-indazolo[2,1-b] phthalazine-triones using 1,3-disulfonic acid imidazolium hydrogen sulfate as a dual-functional catalyst, J. Chem. Technol. Metall., 54 (2019) 23-29.
[4] M.R. Zare, D. Azarifar, O. Badalkhani, M. Jaymand, Sulfonated Magnetic Nanoparticles as Recyclable Catalyst for Facile One-Pot Green Synthesis of 3,4-Dihydro-2H-indazolo[1,2-b] phthalazine-1,6,11(13H)-trione Derivatives, Iran. J. Chem. Chem. Eng., 39, 3(2020) 13-22.
[5] E.J. Noga, G.T. Barthalmus, M.K. Mitchell, Cyclic amines are selective cytotoxic agents for pigmented cells, Cell Biol. Int., 10, 4(1986) 239-247.
[6] F.M. Awadallah, F. Müller, J. Lehmann, A.H. Abadi, Synthesis of novel lactam derivatives and their evaluation as ligands for the dopamine receptors, leading to a D4-selective ligand, Bioorg. Med. Chem., 15, 17(2007) 5811-5818.
[7] N. Hazeri, G. Marandi, M. T Maghsoodlou, S. MH Khorassani, Synthesis of 5H-pyrrolo[1,2-c] imidazoles by Intramolecular Wittig Reaction, Lett. Inorg. Chem., 8, 1(2011) 12-15.
[8] S. ElSakka, A. Soliman, A.M. Imam, Synthesis, antimicrobial activity and Electron Impactof Mass Spectra of Phthalazine-1, 4-dione Derivatives, Afinidad, 66, 540(2009) 167-172.
[9] S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappalà, G. Puja, M. Baraldi, C. De Micheli, Synthesis and anticonvulsant activity of novel and potent 6,7-methylenedioxyphthalazin-1(2H)-ones, J. Med. Chem., 43, 15(2000) 2851-2859.
[10] J. Sinkkonen, V. Ovcharenko, K. Zelenin, I. Bezhan, B. Chakchir, F. Al-Assar, K. Pihlaja, pyridazine-5,8-diones and-1H-pyrazolo[1,2-b] phthalazine-5,10-diones and Their Ring-Chain Tautomerism], Eur. J. Org. Chem, 13 (2002) 2046-2053.
[11] C.-K. Ryu, R.-E. Park, M.-Y. Ma, J.-H. Nho, Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones, Bioorg. Med. Chem. Lett., 17, 9(2007) 2577-2580.
[12] J. Li, Y.-F. Zhao, X.-Y. Yuan, J.-X. Xu, P. Gong, Synthesis and anticancer activities of novel 1,4-disubstituted phthalazines, Molecules, 11, 7(2006) 574-582.
[13] A. Zare, F. Masihpour, Novel ionic liquid N, N-diethyl-N-sulfoethanaminium hydrogen sulfate: Design, characterization, and application as a highly efficient catalyst for the production of triazolo[1,2-a] indazole-triones and 2H-indazolo[2,1-b] phthalazine-triones, Phosphorus Sulfur, 191, 8(2016) 1160-1165.
[14] A. Hasaninejed, M.R. Kazerooni, A. Zare, Solvent-free, one-pot, four-component synthesis of 2H-indazolo[2,1-b] phthalazine-triones using sulfuric acid-modified PEG-6000 as a green recyclable and biodegradable polymeric catalyst, Catal. today, 196, 1(2012) 148-155.
[15] M. Shekouhy, A.M. Sarvestani, S. Khajeh, A. Khalafi-Nezhad, Glycerol: a more benign and biodegradable promoting medium for catalyst-free one-pot multi-component synthesis of triazolo[1,2-a] indazole-triones, RSC Adv., 5, 78(2015) 63705-63710.
[16] D. Verma, V. Sharma, G.S. Okram, S. Jain, Ultrasound-assisted high-yield multicomponent synthesis of triazolo[1,2-a] indazole-triones using silica-coated ZnO nanoparticles as a heterogeneous catalyst, Green Chem., 19, 24(2017) 5885-5899.
[17] A. Bazgir, M. Seyyedhamzeh, Z. Yasaei, P. Mirzaei, A novel three-component method for the synthesis of triazolo[1,2-a] indazole-triones, Tetrahedron Lett., 48, 50(2007) 8790-8794.
[18] E. Mosaddegh, A. Hassankhani, A rapid, one-pot, four-component route to 2H-indazolo[2,1-b] phthalazine-triones, Tetrahedron Lett., 52, 4(2011) 488-490.
[19] M. Kidwai, A. Jahan, R. Chauhan, N.K. Mishra, Dodecylphosphonic acid (DPA): a highly efficient catalyst for the synthesis of 2H-indazolo [2,1-b] phthalazine-triones under solvent-free conditions, Tetrahedron Lett., 53, 14(2012) 1728-1731.
[20] O. Goli-Jolodar, F. Shirini, M. Seddighi, Introduction of a novel nano sized n-sulfonated brönsted acidic homogeneous catalyst for the promotion of the synthesis of 2H-indazolo[2,1-b] phthalazine-1,6,11(13h)-triones, J. Nanosci. Nanotechnol., 18, 1(2018) 591-603.
[21] H.R. Shaterian, M. Ghashang, M. Feyzi, Silica sulfuric acid as an efficient catalyst for the preparation of 2H-indazolo[2,1-b] phthalazine-triones, Appl. Catal. A-Gen., 345, 2(2008) 128-133.
[22] H. Veisi, A. Sedrpoushan, A.R. Faraji, M. Heydari, S. Hemmati, B. Fatahi, A mesoporous SBA-15 silica catalyst functionalized with phenylsulfonic acid groups (SBA-15-Ph-SO3H) as a novel hydrophobic nanoreactor solid acid catalyst for a one-pot three-component synthesis of 2H-indazolo[2,1-b] phthalazine-triones and triazolo[1,2-a] indazole-triones, RSC Adv., 5, 84(2015) 68523-68530.
[23] A.R. Kiasat, J. Davarpanah, Fe3O4@silica sulfuric acid nanoparticles: an efficient reusable nanomagnetic catalyst as potent solid acid for one-pot solvent-free synthesis of indazolo [2, 1-b] phthalazine-triones and pyrazolo[1,2-b] phthalazine-diones, J. Mol. Catal. A Chem., 373, (2013) 46-54.
[24] A. Khazaei, M.A. Zolfigol, R.T. FAAL, G. Chehardoli, S. Mallakpour, Melamine trisulfonic acid (MTSA) as an efficient catalyst for the synthesis of triazolo[1,2-a] indazole-triones and some 2H-indazolo[2,1-b] phthalazine-triones, 3, 4(2013) 211-220.
[25] V. Kamaei, B. Karami, S. Khodabakhshi, Tungstate Sulfuric Acid as a Recyclable Catalyst for the Rapid and Green Synthesis of New and Known α-substituted β-naphthols, Polycycl. Aromat. Compd., 34, 1(2014) 1-11.
[26] M. Farahi, B. Karami, M. Azari, Tungstate sulfuric acid as an efficient catalyst for the synthesis of benzoxazoles and benzothiazoles under solvent-free conditions, C. R. Chim., 16, 11(2013) 1029-1034.
[27] B. Karami, S. Khodabakhshi, Z. Haghighijou, Tungstate sulfuric acid: preparation, characterization, and application in catalytic synthesis of novel benzimidazoles, Chem.Pap., 66, 7(2012) 684-690.
[28] S.S. Rahmatzadeh, B. Karami, S. Khodabakhshi, A modified and practical synthetic route to indazoles and pyrazoles using tungstate sulfuric acid, J. Chin. Chem. Soc., 62, 1(2015) 17-20.
[29] E. Menteşe, I. Doğan, B. Kahveci, Green protocol: Solvent-and catalyst-free synthesis of benzimidazole derivatives via microwave technique, Chem. Heterocycl. Compd., 49, 8(2013) 1136-1140.
[30] M. Shekouhy, A. Hasaninejad, Ultrasound-promoted catalyst-free one-pot four component synthesis of 2H-indazolo [2,1-b] phthalazine-triones in neutral ionic liquid 1-butyl-3-methylimidazolium bromide, Ultrason. Sonochem., 19, 2(2012) 307-313.
[31] G. Shukla, R.K. Verma, G.K. Verma, M.S. Singh, Solvent-free sonochemical one-pot three-component synthesis of 2H-indazolo [2,1-b] phthalazine-1,6, 11-triones and 1H-pyrazolo [1,2-b] phthalazine-5,10-diones, Tetrahedron Lett., 52, 52(2011) 7195-7198.
[32] H.-J. Wang, X.-N. Zhang, Z.-H. Zhang, Highly efficient three-component synthesis of 1H-indazolo [1,2-b] phthalazinetrione derivatives catalyzed by heteropolyacids, Monatsh. Chem., 141, 4(2010) 425-430.
[33] H.R. Shaterian, A. Hosseinian, M. Ghashang, Reusable silica supported poly phosphoric acid catalyzed three-component synthesis of 2H-indazolo [2,1-b] phthalazine-trione derivatives, Arkivoc, 2, 59(2009) 59-67.
[34] D.R. Chandam, A.G. Mulik, P.P. Patil, S.D. Jagdale, D.R. Patil, M.B. Deshmukh, (±)-Camphor-10-sulfonic acid catalyzed atom efficient and green synthesis of triazolo [1,2-a] indazole-triones and spiro triazolo [1,2-a] indazole-tetraones, Res. Chem. Intermed., 41, 2(2015) 761-771.
[35] S.M. Sadeghzadeh, Quinuclidine stabilized on FeNi3 nanoparticles as catalysts for efficient, green, and one‐pot synthesis of triazolo [1,2‐a] indazole‐triones, ChemPlusChem, 79, 2(2014) 278-283.
[36] A. Hasaninejad, A. Zare, M. Shekouhy, Highly efficient synthesis of triazolo [1,2-a] indazole-triones and novel spiro triazolo [1,2-a] indazole-tetraones under solvent-free conditions, Tetrahedron, 67, 2(2011) 390-400.
[37] H.R. Tavakoli, S.M. Moosavi, A. Bazgir, ZrOCl2. 8H2O as an efficient catalyst for the three-component synthesis of triazoloindazoles and indazolophthalazines, J. Korean Chem., Soc., 57, 4(2013) 472-475.
[38] D. Azarifar, R. Nejat-Yami, Z. Akrami, F. Sameri, S. Samadi, Tetrakis (acetonitrile) copper (I) hexafluorophosphate as an efficient catalyst for the synthesis of triazolo [1,2-a]indazole-1,3,8-trione and 2H-indazolo [2,1-b] phthalazine-trione derivatives, Lett. Org. Chem., 9, 2(2012) 128-132.