Synthesis of benzothiazole and benzimidazole derivatives via an eco-friendly method using piperazine immobilized on nano-ZnO-sulfuric acid as a powerful catalyst

Zhang, Q., Zhang, S., Deng, Y.: Recent advances in ionic liquid catalysis. Green Chem. 13, 2619–2637 (2011)

Article  CAS  Google Scholar 

Qiu, X., Wang, Y., Xue, Y., Li, W., Hu, Y.: Laccase immobilized on magnetic nanoparticles modified by amino-functionalized ionic liquid via dialdehyde starch for phenolic compounds biodegradation. Chem. Eng. J. 391, 123564 (2020)

Article  CAS  Google Scholar 

Hagiwara, H., Sekifuji, M., Hoshi, T., Suzuki, T., Quanxi, B., Qiao, K., Yokoyama, C.: Sustainable conjugate addition of indoles catalyzed by acidic ionic liquid immobilized on silica. Synlett 2008, 608–610 (2008)

Article  Google Scholar 

Shirini, F., Seddighi, M., Mazloumi, M., Makhsous, M., Abedini, M.: 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. J. Mol. Liq. 208, 291–297 (2015)

Article  CAS  Google Scholar 

Jin, M.J., Taher, A., Kang, H.J., Choi, M., Ryoo, R.: Palladium acetate immobilized in a hierarchical MFI zeolite-supported ionic liquid: a highly active and recyclable catalyst for Suzuki reaction in water. Green Chem. 11, 309–313 (2009)

Article  CAS  Google Scholar 

Rosli, N.A.H., Loh, K.S., Wong, W.Y., Yunus, R.M., Lee, T.K., Ahmad, A., Chong, S.T.: Review of chitosan-based polymers as proton exchange membranes and roles of chitosan-supported ionic liquids. Int. J. Mol. Sci. 21, 632–684 (2020)

Article  CAS  PubMed  PubMed Central  Google Scholar 

Sharma, R.K., Sharma, S., Dutta, S., Zboril, R., Gawande, M.B.: Silica-nanosphere-based organic–inorganic hybrid nanomaterials: synthesis, functionalization and applications in catalysis. Green Chem. 17, 3207–3230 (2015)

Article  CAS  Google Scholar 

Bagheri, S., Muhd Julkapli, N., Bee Abd Hamid, S.: Titanium dioxide as a catalyst support in heterogeneous catalysis. Sci. World J. 2014, 1–21 (2014)

Article  Google Scholar 

Čepin, M., Jovanovski, V., Podlogar, M., Orel, Z.C.: Amino-and ionic liquid-functionalised nanocrystalline ZnO via silane anchoring–an antimicrobial synergy. J. Mater. Chem. B. 3, 1059–1067 (2015)

Article  PubMed  Google Scholar 

Davarpanah, J., Kiasat, A.R., Noorizadeh, S., Ghahremani, M.: 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. J. Mol. Catal. A: Chem. 376, 78–89 (2013)

Article  CAS  Google Scholar 

Baxter, J.B., Aydil, E.S.: Nanowire-based dye-sensitized solar cells. Appl. Phys. Lett. 86, 053114 (2005)

Article  Google Scholar 

Faisal, A.D., Jaleel, M.A., Kamal, F.Z.: Ethanol gas sensor fabrication based on ZnO flower like nanorods. Eng. Technol. J. 38, 85–97 (2020)

Article  Google Scholar 

Song, J., Zhou, J., Wang, Z.L.: Piezoelectric and semiconducting coupled power generating process of a single ZnO belt/wire. A technology for harvesting electricity from the environment. Nano Lett. 6, 1656–1662 (2006)

Article  CAS  PubMed  Google Scholar 

Massaro, M., Casiello, M., D’Accolti, L., Lazzara, G., Nacci, A., Nicotra, G., Noto, R., Pettignano, A., Spinella, C., Riela, S.: One-pot synthesis of ZnO nanoparticles supported on halloysite nanotubes for catalytic applications. Appl. Clay Sci. 189, 105527 (2020)

Article  CAS  Google Scholar 

Movahedi, F., Masrouri, H., Kassaee, M.Z.: Immobilized silver on surface-modified ZnO nanoparticles: as an efficient catalyst for synthesis of propargylamines in water. J. Mol. Catal. A: Chem. 395, 52–57 (2014)

Article  CAS  Google Scholar 

Mondal, P., Chatterjee, S., Sarkar, P., Bhaumik, A., Mukhopadhyay, C.: Preparation of DABCO-based acidic-ionic-liquid-supported ZnO nanoparticles and their application for ecofriendly synthesis of N-aryl polyhydroquinoline derivatives. ChemistrySelect 4, 11701–11710 (2019)

Article  CAS  Google Scholar 

Karimi-Chayjani, R., Daneshvar, N., Langarudi, M.S.N., Shirini, F., Tajik, H.: Silica-coated magnetic nanoparticles containing bis dicationic bridge for the synthesis of 1,2,4-triazolo pyrimidine/quinazolinone derivatives. J. Mol. Struct. 1199, 126891–126909 (2020)

Article  CAS  Google Scholar 

Huang, S.T., Hsei, I.J., Chen, C.: Synthesis and anticancer evaluation of bis (benzimidazoles), bis (benzoxazoles), and benzothiazoles. Bioorg. Med. Chem. 14, 6106–6119 (2006)

Article  CAS  PubMed  Google Scholar 

Mortimer, C.G., Wells, G., Crochard, J.P., Stone, E.L., Bradshaw, T.D., Stevens, M.F., Westwell, A.D.: 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. J. Med. Chem. 49, 179–185 (2006)

Article  CAS  PubMed  Google Scholar 

Rodríguez-Rodríguez, C., Sanchez de Groot, N., Rimola, A., Alvarez-Larena, A., Lloveras, V., Vidal-Gancedo, J., Ventura, S., Vendrell, J., Sodupe, M., González-Duarte, P.: Design, selection, and characterization of thioflavin-based intercalation compounds with metal chelating properties for application in Alzheimer’s disease. J. Am. Chem. Soc. 131, 1436–1451 (2009)

Article  PubMed  Google Scholar 

Zhu, Y., Zhao, J., Luo, L., Gao, Y., Bao, H., Li, P., Zhang, H.: Research progress of indole compounds with potential antidiabetic activity. Eur. J. Med. Chem. 223, 113665 (2020)

Article  Google Scholar 

Cardellicchio, C., Capozzi, M.A.M., Naso, F.: The Betti base: the awakening of a sleeping beauty. Tetrahedron Asymmetry 21, 507–517 (2010)

Article  CAS  Google Scholar 

Torabi, M., Yarie, M., Zolfigol, M.A., Azizian, S.: Magnetic phosphonium ionic liquid: Application as a novel dual role acidic catalyst for synthesis of 2′-aminobenzothiazolomethylnaphthols and amidoalkyl naphthols. Res. Chem. Intermed. 46, 891–907 (2020)

Article  CAS  Google Scholar 

Kumar, A., Rao, M.S., Rao, V.K.: Sodium dodecyl sulfate-assisted synthesis of 1-(benzothiazolylamino) methyl-2-naphthols in water. Aust. J. Chem. 63, 1538–1540 (2010)

Article  CAS  Google Scholar 

Shaabani, A., Rahmati, A., Farhangi, E.: Water promoted one-pot synthesis of 2′-aminobenzothiazolomethyl naphthols and 5-(2′-aminobenzothiazolomethyl)-6-hydroxyquinolines. Tetrahedron Lett. 48, 7291–7294 (2007)

Article  CAS  Google Scholar 

Shaterian, H.R., Hosseinian, A.: A Brønsted acidic ionic liquid, [(CH2)3SO3 HMIM][HSO4], as an efficient catalyst for synthesis of 1-(benzothiazolylamino) methyl-2-naphthols. Res. Chem. Intermed. 41, 793–801 (2015)

Article  CAS  Google Scholar 

Adrom, B., Maghsoodlou, M.T., Hazeri, N., Lashkari, M.: Solvent-free synthesis of 1-(benzothiazolylamino) methyl-2-naphthols with maltose as green catalyst. Res. Chem. Intermed. 41, 7553–7560 (2015)

Article  CAS  Google Scholar 

Hosseinian, A., Shaterian, H.R.: NaHSO4. H2O catalyzed multicomponent synthesis of 1-(Benzothiazolylamino) methyl-2-naphthols under solvent-free conditions. Phosphorus Sulfur Silicon Relat. Elem. 187, 1056–1063 (2012)

Article  CAS  Google Scholar 

Li, W.L., Wang, L.L., Luo, Q.Y.: One-pot synthesis of 2′-aminobenzothiazolo-arylmethyl-2-naphthols catalyzed by NBS under solvent-free conditions. Sci. World J. 2013, 1–4 (2013)

Google Scholar 

Maghsoodlou, M.T., Karima, M., Lashkari, M., Adrom, B., Aboonajmi, J.: A green protocol for one-pot three-component synthesis of 1-(benzothiazolylamino) methyl-2-naphthol catalyzed by oxalic acid. J. Iran. Chem. Soc. 14, 329–335 (2017)

Article  CAS  Google Scholar 

Sahu, P.K., Sahu, P.K., Agarwal, D.D.: 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. RSC Adv. 5, 69143–69151 (2015)

Article  CAS  Google Scholar 

Nabinia, N., Shirini, F., Tajik, H., Mashhadinezhad, M., Langarudi, M.S.N.: 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. J. Iran. Chem. Soc. 15, 2147–2157 (2018)

Article  CAS  Google Scholar 

Goli-Jolodar, O., Shirini, F., Seddighi, M.: Introduction of O-sulfonated poly(vinylpyrrolidonium) hydrogen sulfate as an efficient, and reusable solid acid catalyst for some solvent-free multicomponent reactions. RSC Adv. 6, 44794–44806 (2016)

Article  CAS  Google Scholar 

Trivedi, A.R., Bhuva, V.R., Dholariya, B.H., Dodiya, D.K., Kataria, V.B., Shah, V.H.: Novel dihydropyrimidines as a potential new class of antitubercular agents. Bioorg. Med. Chem. Lett. 20, 6100–6102 (2010)

Article  CAS  PubMed  Google Scholar 

Safari, S., Ghavimi, R., Razzaghi-Asl, N., Sepehri, S.: Synthesis, biological evaluation and molecular docking study of dihydropyrimidine derivatives as potential anticancer agents. J. Heterocycl. Chem. 57, 1023–1033 (2020)

Article  CAS  Google Scholar 

Alam, O., Khan, S.A., Siddiqui, N., Ahsan, W., Verma, S.P., Gilani, S.J.: Antihypertensive activity of newer 1, 4-dihydro-5-pyrimidine carboxamides: Synthesis and pharmacological evaluation. Eur. J. Med. Chem. 45, 5113–5119 (2010)

Article  CAS  PubMed  Google Scholar 

Sawant, R.L., Sarode, V.I., Jadhav, G.D., Wadekar, J.B.: Synthesis, molecular docking, and cardioprotective activity of 2-methylthio-1,4-dihydropyrimidines. Med. Chem. Res. 21, 1825–1832 (2012)

Article  CAS  Google Scholar 

Meshram, H.M., Kumar, A.S., Kumar, G.S., Swetha, A., Reddy, B.C., Ramesh, P.: Boric acid promoted an efficient and practical synthesis of fused pyrimidines in aqueous media. Der Pharma Chem. 4, 956–960 (2012)

CAS  Google Scholar 

Khodamorady, M., Sohrabnezhad, S., Bahrami, K.: 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. Polyhedron 178, 114340 (2020)

Article  CAS  Google Scholar 

Heidarizadeh, F., Rezaee Nezhad, E., Sajjadifar, S.: Novel acidic ionic liquid as a catalyst and solvent for green synthesis of dihydropyrimidine derivatives. Sci. Iran. 20, 561–565 (2013)

CAS  Google Scholar 

Liu, J., Lei, M., Hu, L.: Thiamine hydrochloride (VB1): an efficient promoter for the one-pot synthes

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