Multicomponent Synthesis of Tetrahydrobenzo[a]xanthene and Tetrahydrobenzo[a]acridine Derivatives using Sulfonated Multi-Walled Carbon Nanotubes as Heterogeneous Nanocatalysts
Subject Areas : Iranian Journal of Catalysis
Shakir Saied
1
,
Mohanad Saleh
2
,
Ahmed Hamdoon
3
1 - Department of Medical Laboratory Techniques, Al-Noor University College, Bartella, Iraq
2 - Department of Chemistry, College of Education for Pure Science, Mosul University, Mosul-Iraq
3 - Branch of Basic Science, College of Agriculture and Forestry, University of Mosul, Iraq
Keywords:
Abstract :
[1] L.-C. Qin, X. Zhao, K. Hirahara, Y. Miyamoto, Y. Ando, S. Iijima, The smallest carbon nanotube, Nature, 408 (2000) 50-50.
[2] F. Rodríguez-reinoso, The role of carbon materials in heterogeneous catalysis, Carbon, 36 (1998) 159-175.
[3] M. Trojanowicz, Analytical applications of carbon nanotubes: a review, TrAC, Trends Anal. Chem., 25 (2006) 480-489.
[4] T. Belin, F. Epron, Characterization methods of carbon nanotubes: a review, Mater. Sci. Eng.: B, 119 (2005) 105-118.
[5] V. Campisciano, L. Valentino, A. Morena, A. Santiago-Portillo, N. Saladino, M. Gruttadauria, C. Aprile, F. Giacalone, Carbon nanotube supported aluminum porphyrin-imidazolium bromide crosslinked copolymer: A synergistic bifunctional catalyst for CO2 conversion, J. CO2 Utiliz., 57 (2022) 101884.
[6] C. Zhao, J. Yang, Y. Sang, R. Zhang, M. Zhu, T. Li, H. Xu, Ultrafine palladium nanoparticles supported on poly(4-vinylpyridine)-grafted carbon nanotubes as heterogeneous catalysts for cross-coupling reaction between organoindium halide and alkyl iodide, Colloids Surf. Physicochem. Eng. Aspects, 627 (2021) 127215.
[7] I. Pernik, A. Desmecht, B.A. Messerle, S. Hermans, O. Riant, Dendrimeric and Corresponding Monometallic Iridium(III) Catalysts Bound to Carbon Nanotubes Used in Hydroamination Transformations, Eur. J. Inorg. Chem., 2021 (2021) 3448-3457.
[8] H. Saeidiroshan, L. Moradi, Multiwalled carbon nanotubes/guanidine/Ni (II): A new and effective organometallic catalyst for the green synthesis of pyrazolopyranopyrimidines, Appl. Organomet. Chem., 35 (2021) e6142.
[9] K. Wu, Y. Bai, D. Chen, L. Chen, Y. Huang, S. Bai, Y. Li, Green synthesis of 1,4-dihydropyridines using cobalt carbon nanotubes as recyclable catalysts, Environ. Chem. Lett., 19 (2021) 1903-1910.
[10] R. Fareghi-Alamdari, M. Golestanzadeh, F. Agend, N. Zekri, Synthesis, characterization and catalytic activity of sulphonated multi-walled carbon nanotubes as heterogeneous, robust and reusable catalysts for the synthesis of bisphenolic antioxidants under solvent-free conditions, J. Chem. Sci., 125 (2013) 1185-1195.
[11] F.-A. Reza, G. Mohsen, A. Farima, Z. Negar, Regiospecific, one-pot, and pseudo-five-component synthesis of 6,6′-(arylmethylene)bis(2-(tert-butyl)4-methylphenol) antioxidants using highly sulfonated multi-walled carbon nanotubes under solvent-free conditions, Can. J. Chem., 91 (2013) 982-991.
[12] M. Golestanzadeh, H. Naeimi, Effect of Confined Spaces in the Catalytic Activity of 1D and 2D Heterogeneous Carbon-Based Catalysts for Synthesis of 1,3,5-Triarylbenzenes: RGO-SO3H vs. MWCNTs-SO3H, ChemistrySelect, 4 (2019) 1909-1921.
[13] R. Fareghi-Alamdari, M. Golestanzadeh, N. Zekri, Solvent-free synthesis of trisphenols as starting precursors for the synthesis of calix[4]arenes using sulfonated multi-walled carbon nanotubes, New J. Chem., 40 (2016) 3400-3412.
[14] R. Fareghi-Alamdari, M. Golestanzadeh, N. Zekri, Z. Mavedatpoor, Multi SO3H supported on carbon nanotubes: a practical, reusable, and regioselective catalysts for the tert-butylation of p-cresol under solvent-free conditions, J. Iran. Chem. Soc., 12 (2015) 537-549.
[15] R. Fareghi-Alamdari, M. Golestanzadeh, F. Agend, N. Zekri, Application of highly sulfonated single-walled carbon nanotubes: An efficient heterogeneous catalyst for the one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions, C. R. Chim., 16 (2013) 878-887.
[16] L. Moradi, G.R. Najafi, H. Saeidiroshan, New method for preparation of MWCNT-SO3H as an efficient and reusable catalyst for the solvent-free synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones/thiones, Iran. J. Catal., 5 (2015) 357-364.
[17] M.A. Abdel-Lateef, A. Almahri, S.M. Derayea, E. Samir, Xanthene based resonance Rayleigh scattering and spectrofluorimetric probes for the determination of cyclobenzaprine: Application to content uniformity test, Rev. Anal. Chem, 39 (2020) 222-230.
[18] T. Kitano, T. Komuro, H. Tobita, Double and Single Hydroboration of Nitriles Catalyzed by a Ruthenium–Bis(silyl)xanthene Complex: Application to One-Pot Synthesis of Diarylamines and N-Arylimines, Organometallics, 38 (2019) 1417-1420.
[19] G. Zhao, Y. Sun, H. Duan, Four xanthene–fluorene based probes for the detection of Hg2+ ions and their application in strip tests and biological cells, New J. Chem., 45 (2021) 685-695.
[20] S.M. Derayea, D.M. Nagy, Application of a xanthene dye, eosin Y, as spectroscopic probe in chemical and pharmaceutical analysis; a review, Rev. Anal. Chem, 37 (2018).
[21] A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, Nickel(II) immobilized on dithizone–boehmite nanoparticles: as a highly efficient and recyclable nanocatalyst for the synthesis of polyhydroquinolines and sulfoxidation reaction, J. Iran. Chem. Soc., 16 (2019) 511-521.
[22] M. Nikoorazm, B. Tahmasbi, S. Gholami, P. Moradi, Copper and nickel immobilized on cytosine@MCM-41: as highly efficient, reusable and organic–inorganic hybrid nanocatalysts for the homoselective synthesis of tetrazoles and pyranopyrazoles, Appl. Organomet. Chem., 34 (2020) e5919.
[23] B. Atashkar, A. Rostami, H. Gholami, B. Tahmasbi, Magnetic nanoparticles Fe3O4-supported guanidine as an efficient nanocatalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions, Res. Chem. Intermed., 41 (2015) 3675-3681.
[24] P. Moradi, M. Hajjami, Magnetization of biochar nanoparticles as a novel support for fabrication of organo nickel as a selective, reusable and magnetic nanocatalyst in organic reactions, New J. Chem., 45 (2021) 2981-2994.
[25] A.T. Smith, A.M. LaChance, S. Zeng, B. Liu, L. Sun, Synthesis, properties, and applications of graphene oxide/reduced graphene oxide and their nanocomposites, Nano Mater. Sci., 1 (2019) 31-47.
[26] B. Tahmasbi, A. Ghorbani-Choghamarani, P. Moradi, Palladium fabricated on boehmite as an organic–inorganic hybrid nanocatalyst for C–C cross coupling and homoselective cycloaddition reactions, New J. Chem., 44 (2020) 3717-3727.
[27] M. Koolivand, M. Nikoorazm, A. Ghorbani-Choghamarani, R. Azadbakht, B. Tahmasbi, Ni–citric acid coordination polymer as a practical catalyst for multicomponent reactions, Sci. Rep., 11 (2021) 24475.
[28] M. Nikoorazm, P. Moradi, N. Noori, L-cysteine complex of palladium onto mesoporous channels of MCM-41 as reusable, homoselective and organic–inorganic hybrid nanocatalyst for the synthesis of tetrazoles, J. Porous Mater., 27 (2020) 1159-1169.
[29] P. Moradi, M. Hajjami, B. Tahmasbi, Fabricated copper catalyst on biochar nanoparticles for the synthesis of tetrazoles as antimicrobial agents, Polyhedron, 175 (2020) 114169.
[30] A. Jabbari, B. Tahmasbi, M. Nikoorazm, A. Ghorbani-Choghamarani, A new Pd-Schiff-base complex on boehmite nanoparticles: Its application in Suzuki reaction and synthesis of tetrazoles, Appl. Organomet. Chem., 32 (2018) e4295.
[31] J.M. Khurana, D. Magoo, pTSA-catalyzed one-pot synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones in ionic liquid and neat conditions, Tetrahedron Lett., 50 (2009) 4777-4780.
[32] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, M. Khojasteh, Z. Asgari, V. Khakyzadeh, A. Khalafi-Nezhad, Organocatalyst trityl chloride efficiently promoted the solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones by in situ formation of carbocationic system in neutral media, Catal. Commun., 20 (2012) 54-57.
[33] H.T. Nguyen, N.-P. Thi Le, D.-K. Nguyen Chau, P.H. Tran, New nano-Fe3O4-supported Lewis acidic ionic liquid as a highly effective and recyclable catalyst for the preparation of benzoxanthenes and pyrroles under solvent-free sonication, RSC Adv., 8 (2018) 35681-35688.
[34] J. Ma, X. Peng, L. Zhong, R. Sun, Sulfonation of carbonized xylan-type hemicellulose: a renewable and effective biomass-based biocatalyst for the synthesis of O- and N-heterocycles, New J. Chem., 42 (2018) 9140-9150.
[35] A. Sethukumar, V. Vithya, C. Udhaya Kumar, B. Arul Prakasam, NMR spectral and structural studies on some xanthenones and their thiosemicarbazone derivatives: Crystal and molecular structure of 12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one, J. Mol. Struct., 1008 (2012) 8-16.
[36] A.K. Dutta, P. Gogoi, S. Saikia, R. Borah, N,N-disulfo-1,1,3,3-tetramethylguanidinium carboxylate ionic liquids as reusable homogeneous catalysts for multicomponent synthesis of tetrahydrobenzo[a]xanthene and tetrahydrobenzo[a]acridine derivatives, J. Mol. Liq., 225 (2017) 585-591.
[37] L. Kheirkhah, M. Mamaghani, A. Yahyazadeh, N.O. Mahmoodi, HAp-encapsulated γ-Fe2O3-supported dual acidic heterogeneous catalyst for highly efficient one-pot synthesis of benzoxanthenones and 3-pyranylindoles, Appl. Organomet. Chem., 32 (2018) e4072.
[38] H.R. Shaterian, M. Mohammadnia, Nanocrystalline TiO2–HClO4 catalyzed three-component preparation of derivatives of 1-amidoalkyl-2-naphthol, 1-carbamato-alkyl-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, and 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one, Res. Chem. Intermed., 39 (2013) 4221-4237.
[39] H. Zang, Y. Zhang, Y. Mo, B. Cheng, Ultrasound-Promoted One-Pot Synthesis of 7-Aryl-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one Derivatives, Synth. Commun., 41 (2011) 3207-3214.
[40] M.K. Karkhah, H. Kefayati, S. Shariati, Synthesis of benzo[h]quinolone and benzo[c]acridinone derivatives by Fe3O4@PS-Arginine[HSO4] as an efficient magnetic nanocatalyst, J. Heterocycl. Chem., 57 (2020) 4181-4191.
[41] M.M. Heravi, H. Alinejhad, F. Derikvand, H.A. Oskooie, B. Baghernejad, F.F. Bamoharram, NH2SO3H and H6P2W18O62 · 18H2O-Catalyzed, Three-Component, One-Pot Synthesis of Benzo[c]acridine Derivatives, Synth. Commun., 42 (2012) 2033-2039.
[42] M.R. Poor Heravi, P. Aghamohammadi, l-Proline-catalysed one-pot synthesis of tetrahydrobenzo[c]acridin-8(7H)-ones at room temperature, C. R. Chim., 15 (2012) 448-453.
[43] M. Asemani, A.R. Rabbani, Detailed FTIR spectroscopy characterization of crude oil extracted asphaltenes: Curve resolve of overlapping bands, Journal of Petroleum Science and Engineering, 185 (2020) 106618.
[44] F. Sharif, A.S. Zeraati, P. Ganjeh-Anzabi, N. Yasri, M. Perez-Page, S.M. Holmes, U. Sundararaj, M. Trifkovic, E.P.L. Roberts, Synthesis of a high-temperature stable electrochemically exfoliated graphene, Carbon, 157 (2020) 681-692.
[45] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, Preparation, characterization and application of ionic liquid sulfonic acid functionalized pyridinium chloride as an efficient catalyst for the solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones, J. Mol. Liq., 186 (2013) 63-69.
[46] B. Sadeghi, Silica supported boron trifluoride nanoparticles(BF3-SiO2 NPs): An efficient and reusable catalyst for one-pot synthesis of benzo[a]xanthene-11-onederivatives, Sci. Iranica, 21 (2014) 708-714.
[47] H. Zang, Y. Zhang, Y. Zang, B.-W. Cheng, An efficient ultrasound-promoted method for the one-pot synthesis of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives, Ultrason. Sonochem., 17 (2010) 495-499.
[48] S. Khaksar, N. Behzadi, Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for one-pot condensation of β-naphthol, aldehydes and cyclic 1, 3-dicarbonyl compounds, Combinatorial Chem. High Throughput Screening, 15 (2012) 845-848.
[49] F. Karimirad, F.K. Behbahani, γ-Fe2O3@Si-(CH2)3@mel@(CH2)4SO3H as a magnetically bifunctional and retrievable nanocatalyst for green synthesis of benzo[c]acridine-8(9H)-ones and 2-amino-4H-chromenes, Inorganic and Nano-Metal Chemistry, 51 (2021) 656-666.
