Synthesis of benzothiazole and benzimidazole derivatives via an eco-friendly method using piperazine immobilized on nano-ZnO-sulfuric acid as a powerful catalyst
- Department of Chemistry, College of Sciences, University of Guilan, Rasht, 41335-19141, IR
Published in Issue 14-10-2021
How to Cite
Mousapour, M., & Shirini, F. (2021). Synthesis of benzothiazole and benzimidazole derivatives via an eco-friendly method using piperazine immobilized on nano-ZnO-sulfuric acid as a powerful catalyst. Journal of Nanostructure in Chemistry, 13(4 (August 2023). https://doi.org/10.1007/s40097-021-00450-5
Abstract
Abstract In this research, the synthesis of piperazine immobilized on nano-ZnO-sulfuric acid (PINZS) as a new piperazine-based nano-reagent is reported. After identification of PINZS using different techniques including XRD (X-ray powder diffraction), TGA (thermogravimetric analysis), FT-IR (Fourier transform infrared spectroscopy), FESEM (field emission scanning electron microscopy), and EDX (energy-dispersive X-ray) analysis, this reagent is efficiently used for the synthesis of 1-(benzothiazolylamino) phenylmethyl-2-naphthols and pyrimido[1, 2-a]benzimidazoles via a domino Knoevenagel/Michael sequence which identified acceptable reaction times (7–45 min.), great yields (up to 98%) and ease of the preparation, separation, and recovery of PINZS (for three times) as the most important features of this protocol. Graphic abstract Use of PINZS in the synthesis of some important heterocycles.Keywords
- ZnO NPs,
- Piperazine,
- Immobilized ionic liquids,
- Multi-component reactions,
- Pyrimido[1,2-a]benzimidazole,
- 1-(Benzothiazolylamino) phenylmethyl-2-naphthol
References
- Zhang et al. (2011) Recent advances in ionic liquid catalysis (pp. 2619-2637) https://doi.org/10.1039/c1gc15334j
- Qiu et al. (2020) Laccase immobilized on magnetic nanoparticles modified by amino-functionalized ionic liquid via dialdehyde starch for phenolic compounds biodegradation https://doi.org/10.1016/j.cej.2019.123564
- Hagiwara et al. (2008) Sustainable conjugate addition of indoles catalyzed by acidic ionic liquid immobilized on silica (pp. 608-610) https://doi.org/10.1055/s-2008-1032082
- Shirini et al. (2015) One-pot synthesis of 4, 4ʹ-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols) catalyzed by Brönsted acidic ionic liquid supported on nanoporous Na+-montmorillonite (pp. 291-297) https://doi.org/10.1016/j.molliq.2015.04.027
- Jin et al. (2009) Palladium acetate immobilized in a hierarchical MFI zeolite-supported ionic liquid: a highly active and recyclable catalyst for Suzuki reaction in water (pp. 309-313) https://doi.org/10.1039/b817855k
- Rosli et al. (2020) Review of chitosan-based polymers as proton exchange membranes and roles of chitosan-supported ionic liquids (pp. 632-684) https://doi.org/10.3390/ijms21020632
- Sharma et al. (2015) Silica-nanosphere-based organic–inorganic hybrid nanomaterials: synthesis, functionalization and applications in catalysis (pp. 3207-3230) https://doi.org/10.1039/C5GC00381D
- Bagheri et al. (2014) Titanium dioxide as a catalyst support in heterogeneous catalysis (pp. 1-21) https://doi.org/10.1155/2014/727496
- Čepin et al. (2015) Amino-and ionic liquid-functionalised nanocrystalline ZnO via silane anchoring–an antimicrobial synergy (pp. 1059-1067) https://doi.org/10.1039/C4TB01300J
- Davarpanah et al. (2013) Nano magnetic double-charged diazoniabicyclo [2.2.2] octane dichloride silica hybrid: synthesis, characterization, and application as an efficient and reusable organic–inorganic hybrid silica with ionic liquid framework for one-pot synthesis of pyran annulated heterocyclic compounds in water (pp. 78-89) https://doi.org/10.1016/j.molcata.2013.04.020
- Baxter and Aydil (2005) Nanowire-based dye-sensitized solar cells https://doi.org/10.1063/1.1861510
- Faisal et al. (2020) Ethanol gas sensor fabrication based on ZnO flower like nanorods (pp. 85-97) https://doi.org/10.30684/etj.v38i3B.279
- Song et al. (2006) Piezoelectric and semiconducting coupled power generating process of a single ZnO belt/wire. A technology for harvesting electricity from the environment (pp. 1656-1662) https://doi.org/10.1021/nl060820v
- Massaro et al. (2020) One-pot synthesis of ZnO nanoparticles supported on halloysite nanotubes for catalytic applications https://doi.org/10.1016/j.clay.2020.105527
- Movahedi et al. (2014) Immobilized silver on surface-modified ZnO nanoparticles: as an efficient catalyst for synthesis of propargylamines in water (pp. 52-57) https://doi.org/10.1016/j.molcata.2014.08.007
- Mondal et al. (2019) Preparation of DABCO-based acidic-ionic-liquid-supported ZnO nanoparticles and their application for ecofriendly synthesis of N-aryl polyhydroquinoline derivatives (pp. 11701-11710) https://doi.org/10.1002/slct.201902427
- Karimi-Chayjani et al. (2020) Silica-coated magnetic nanoparticles containing bis dicationic bridge for the synthesis of 1,2,4-triazolo pyrimidine/quinazolinone derivatives (pp. 126891-126909) https://doi.org/10.1016/j.molstruc.2019.126891
- Huang et al. (2006) Synthesis and anticancer evaluation of bis (benzimidazoles), bis (benzoxazoles), and benzothiazoles (pp. 6106-6119) https://doi.org/10.1016/j.bmc.2006.05.007
- Mortimer et al. (2006) Antitumor benzothiazoles. 26. 2-(3, 4-dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines (pp. 179-185) https://doi.org/10.1021/jm050942k
- Rodríguez-Rodríguez et al. (2009) Design, selection, and characterization of thioflavin-based intercalation compounds with metal chelating properties for application in Alzheimer’s disease (pp. 1436-1451) https://doi.org/10.1021/ja806062g
- Zhu et al. (2020) Research progress of indole compounds with potential antidiabetic activity https://doi.org/10.1016/j.ejmech.2021.113665
- Cardellicchio et al. (2010) The Betti base: the awakening of a sleeping beauty (pp. 507-517) https://doi.org/10.1016/j.tetasy.2010.03.020
- Torabi et al. (2020) Magnetic phosphonium ionic liquid: Application as a novel dual role acidic catalyst for synthesis of 2′-aminobenzothiazolomethylnaphthols and amidoalkyl naphthols (pp. 891-907) https://doi.org/10.1007/s11164-019-03996-w
- Kumar et al. (2010) Sodium dodecyl sulfate-assisted synthesis of 1-(benzothiazolylamino) methyl-2-naphthols in water (pp. 1538-1540) https://doi.org/10.1071/CH10209
- Shaabani et al. (2007) Water promoted one-pot synthesis of 2′-aminobenzothiazolomethyl naphthols and 5-(2′-aminobenzothiazolomethyl)-6-hydroxyquinolines (pp. 7291-7294) https://doi.org/10.1016/j.tetlet.2007.08.042
- Shaterian and Hosseinian (2015) A Brønsted acidic ionic liquid, [(CH2)3SO3 HMIM][HSO4], as an efficient catalyst for synthesis of 1-(benzothiazolylamino) methyl-2-naphthols (pp. 793-801) https://doi.org/10.1007/s11164-013-1230-0
- Adrom et al. (2015) Solvent-free synthesis of 1-(benzothiazolylamino) methyl-2-naphthols with maltose as green catalyst (pp. 7553-7560) https://doi.org/10.1007/s11164-014-1843-y
- Hosseinian and Shaterian (2012) NaHSO4. H2O catalyzed multicomponent synthesis of 1-(Benzothiazolylamino) methyl-2-naphthols under solvent-free conditions (pp. 1056-1063) https://doi.org/10.1080/10426507.2012.664221
- Li et al. (2013) One-pot synthesis of 2′-aminobenzothiazolo-arylmethyl-2-naphthols catalyzed by NBS under solvent-free conditions (pp. 1-4)
- Maghsoodlou et al. (2017) A green protocol for one-pot three-component synthesis of 1-(benzothiazolylamino) methyl-2-naphthol catalyzed by oxalic acid (pp. 329-335) https://doi.org/10.1007/s13738-016-0981-0
- Sahu et al. (2015) Role of basicity and the catalytic activity of KOH loaded MgO and hydrotalcite as catalysts for the efficient synthesis of 1-[(2-benzothiazolylamino) arylmethyl]-2-naphthalenols (pp. 69143-69151) https://doi.org/10.1039/C5RA11857C
- Nabinia et al. (2018) An affordable DABCO-based ionic liquid efficiency in the synthesis of 3-amino-1-aryl-1H-benzo[f] chromene-2- carbonitrile, 1-(benzothiazolylamino) phenylmethyl-2-naphthol, and 1-(benzoimidazolylamino) phenylmethyl-2-naphthol derivatives (pp. 2147-2157) https://doi.org/10.1007/s13738-018-1408-x
- Goli-Jolodar et al. (2016) Introduction of O-sulfonated poly(vinylpyrrolidonium) hydrogen sulfate as an efficient, and reusable solid acid catalyst for some solvent-free multicomponent reactions (pp. 44794-44806) https://doi.org/10.1039/C6RA08486A
- Trivedi et al. (2010) Novel dihydropyrimidines as a potential new class of antitubercular agents (pp. 6100-6102) https://doi.org/10.1016/j.bmcl.2010.08.046
- Safari et al. (2020) Synthesis, biological evaluation and molecular docking study of dihydropyrimidine derivatives as potential anticancer agents (pp. 1023-1033) https://doi.org/10.1002/jhet.3822
- Alam et al. (2010) Antihypertensive activity of newer 1, 4-dihydro-5-pyrimidine carboxamides: Synthesis and pharmacological evaluation (pp. 5113-5119) https://doi.org/10.1016/j.ejmech.2010.08.022
- Sawant et al. (2012) Synthesis, molecular docking, and cardioprotective activity of 2-methylthio-1,4-dihydropyrimidines (pp. 1825-1832) https://doi.org/10.1007/s00044-011-9700-7
- Meshram et al. (2012) Boric acid promoted an efficient and practical synthesis of fused pyrimidines in aqueous media (pp. 956-960)
- Khodamorady et al. (2020) Efficient one-pot synthetic methods for the preparation of 3, 4-dihydropyrimidinones and 1, 4-dihydropyridine derivatives using BNPs@ SiO2 (CH2)3NHSO3H as a ligand and metal free acidic heterogeneous nano-catalyst https://doi.org/10.1016/j.poly.2019.114340
- Heidarizadeh et al. (2013) Novel acidic ionic liquid as a catalyst and solvent for green synthesis of dihydropyrimidine derivatives (pp. 561-565)
- Liu et al. (2012) Thiamine hydrochloride (VB1): an efficient promoter for the one-pot synthesis of benzo [4, 5] imidazo [1,2-a] pyrimidine and [1, 2, 4] triazolo [1, 5-a] pyrimidine derivatives in water medium (pp. 840-846) https://doi.org/10.1039/c2gc16499j
- Kaur et al. (2015) One-pot synthesis of tricyclic dihydropyrimidine derivatives and their biological evaluation (pp. 332-337) https://doi.org/10.1016/j.tet.2014.11.039
- Yao et al. (2010) Three-component synthesis of 4-aryl-1H-pyrimido [1, 2-a] benzimidazole derivatives in ionic liquid (pp. 26-32)
- Basyouni et al. (2020) Silica sulfuric acid/ethylene glycol: An efficient eco-friendly catalyst for one-pot synthesis of new benzo [4, 5] imidazo [1, 2-a] pyrimidines (pp. 249-260) https://doi.org/10.1080/00304948.2020.1761692
- Seyedakbari et al. (2013) Multicomponent synthesis of benzo [4, 5] imidazo [1, 2-a] pyrimidine derivatives using novel ionic liquid supported nanoporous silica and their antimicrobial properties (pp. 832-837)
- Ghorbani-Vaghei et al. (2014) One-pot synthesis of pyrimido [1, 2-a] benzimidazoles under solvent-free conditions (pp. 979-984) https://doi.org/10.1002/hlca.201300361
- Reddy et al. (2014) p-Toluenesulfonic acid-catalyzed one-pot synthesis of 2-amino-4-substituted-1, 4-dihydrobenzo [4, 5] imidazolo [1, 2-a] pyrimidine-3-carbonitriles under neat conditions (pp. 484-489) https://doi.org/10.1016/j.crci.2013.08.007
- Shaabani et al. (2007) Clean Synthesis in Water: Uncatalyzed Three-component condensation reaction of 3-amino-1, 2, 4-triazole or 2-aminobenzimidazole with aldehyde in the presence of activated CH-acids (pp. 973-979) https://doi.org/10.1002/qsar.200620024
- Abedini et al. (2016) Poly (vinylpyrrolidinium) perchlorate as a new and efficient catalyst for the promotion of the synthesis of polyhydroquinoline derivatives via Hantzsch condensation (pp. 2303-2315) https://doi.org/10.1007/s11164-015-2150-y
- Kamali and Shirini (2017) Introduction of Fe3O4@ SiO2–ZrCl2-MNPs for the efficient promotion of some multi-component reactions under solvent-free conditions (pp. 11778-11791) https://doi.org/10.1039/C7NJ01863K
- Khoshdel et al. (2021) Three-component synthesis of 4 H-pyran scaffolds accelerated by a gabapentin-based natural deep eutectic solvent (pp. 3138-3149) https://doi.org/10.1039/D0NJ05342B
- Salehi et al. (2006) Silica sulfuric acid and silica chloride as efficient reagents for organic reactions (pp. 2171-2189) https://doi.org/10.2174/138527206778742650
- Kołodziejczak-Radzimska et al. (2012) Structural characterisation of ZnO particles obtained by the emulsion precipitation method (pp. 1-9) https://doi.org/10.1155/2012/656353
- Phukan et al. (2020) Zinc Oxide nanoparticles catalysed one-pot three-component reaction: A facile synthesis of 4-Aryl-NH-1,2,3-triazoles (pp. 2208-2219) https://doi.org/10.1007/s10562-020-03143-w
- Chunduri et al. (2017) Streptavidin conjugated ZnO nanoparticles for early detection of HIV infection (pp. 472-480) https://doi.org/10.5185/amlett.2017.6579
- Seddighi et al. (2015) Brønsted acidic ionic liquid supported on rice husk ash (RHA-[pmim] HSO4): A highly efficient and reusable catalyst for the synthesis of 1-(benzothiazolylamino) phenylmethyl-2-naphthols (pp. 573-580) https://doi.org/10.1016/j.crci.2014.09.003
- Maghsoodlou et al. (2016) Convenient approach for the one-pot, three-component synthesis of 1-(benzothiazolylamino) methyl-2-naphthol using fumaric acid as a green catalyst (pp. 369-372)
- Kamali and Shirini (2018) Fe3O4@ SiO2–ZrCl2-MNPs: A novel magnetic catalyst for the clean and efficient cascade synthesis of 1-(benzothiazolylamino) methyl-2-naphthol derivatives in the absence of solvent https://doi.org/10.1002/aoc.3972
- Kalavagunta et al. (2014) Design and green synthesis of 2-(diarylalkyl) aminobenzothiazole derivatives and their dual activities as angiotensin converting enzyme inhibitors and calcium channel blockers (pp. 344-354) https://doi.org/10.1016/j.ejmech.2014.06.035
- Sahu et al. (2015) Synthesis and evaluation of antimicrobial activity of 2-aminobenzothiazolomethyl naphthol derivatives (pp. 725-736) https://doi.org/10.1007/s00044-014-1150-6
- Abedini et al. (2016) Poly (vinylpyrrolidonium) perchlorate catalyzed one-pot synthesis of tricyclic dihydropyrimidine derivatives (pp. 6221-6229) https://doi.org/10.1007/s11164-016-2456-4
- Chavan et al. (2020) Synthesis of substituted pyrimidine using ZnFe2O4 nanocatalyst via one pot multi-component reaction ultrasonic irradiation (pp. 3326-3333)
- Benzekri et al. (2020) NH3(CH2)5NH3BiCl5 as a new hybrid and efficient catalyst for the synthesis of 1-(benzothiazolylamino) methyl-2-naphthol derivatives under solvent-free conditions (pp. 127308-127018) https://doi.org/10.1016/j.molstruc.2019.127308
- Javanshir et al. (2014) Ultrasound-promoted, rapid, green, one-pot synthesis of 2′-aminobenzothiazolomethylnaphthols via a multi-component reaction, catalyzed by heteropolyacid in aqueous media (pp. 502-506) https://doi.org/10.1016/j.jscs.2011.10.013
- Yang (2012) Trichloroisocyanuric acid, a new and efficient catalyst for the synthesis of 2′-aminobenzothiazolo-arylmethyl-2-naphthols (pp. 2424-2428) https://doi.org/10.1155/2012/707324
- Sahu et al. (2014) Role of surfactant and micelle-promoted mild, efficient, sustainable synthesis of 2-aminobenzothiazolomethyl naphthols and 5-(2-aminobenzothiazolomethyl)-6-hydroxyquinolines in water at room temperature (pp. 40414-40420) https://doi.org/10.1039/C4RA03847A
- Survase et al. (2017) Polyethylene glycol-promoted synthesis of pyrimido [1,2-a] benzimidazole and pyrano [2, 3-c] pyrazole derivatives in water (pp. 680-687) https://doi.org/10.1080/00397911.2017.1278774