Sulfonic acid-supported vanillin/bis indolylmethane-functionalized Fe₃O₄@SiO₂-propyl NPs as green, effective, and magnetically recoverable catalysts for the synthesis of imidazoquinazolines and thiazoquinazolines

References

• Zhang Y, Zhang Y, Liu J, et al. Synthesis and in vitro biological evaluation of novel quinazoline derivatives. Bioorg Med Chem Lett. 2017;27:1584–1587.
   PubMed Web of Science ®Google Scholar
• Hamed MM, Darwish SS, Herrmann J, et al. First bispecific inhibitors of the epidermal growth receptor kinase and the NF-κB activity as novel anticancer agents. J Med Chem. 2017;60:2853–2868.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Cao XB, Ren LM. Doxazosin selectively potentiates contraction to serotonin via 5-HT2A receptors in longitudinal muscle strips of the rabbit gastric body. Canadian J Physiol Pharmacol. 2014;92:197.
   PubMed Web of Science ®Google Scholar
• McKay RG, Miller MJ, Ferguson JJ, et al. Assessment of left ventricular end-systolic pressure-volume relations with an impedance catheter and transient inferior vena cava occlusion: use of this system in the evaluation of the cardiotonic effects of dobutamine, milrinone, posicor and epinephrine. J Am Coll Cardiol. 1986;8:1152–1160.
   PubMed Web of Science ®Google Scholar
• Cheng J, Thompson MA, Walker HJ, et al. Lixazinone stimulates mitogenesis of Madin-Darby canine kidney cells. Exp Biol Med. 2006;231:288–295.
   Web of Science ®Google Scholar
• Hidalgo SA, Colomer MP. Int. PCT Pub. No. EP/2015/2915526 A1; 2015.
   Google Scholar
• Ishikawa F, Yamaguchi H, Saegusa J, et al. Cyclic guanidines. XVI. Synthesis and biological activities of tetracyclic imidazo [2, 1-b] quinazolinone derivatives. Chem Pharm Bull. 1985;33:3336–3348.
   PubMed Web of Science ®Google Scholar
• Scott RB, Downey KM, Healy KP, et al. Synthesis and stability of 3-hydroxy anagrelide, a biologically potent metabolite of anagrelide. Heterocycles. 2012;86:1637–1646.
   Web of Science ®Google Scholar
• Srivastava GK, Kesarwani AP, Grover RK. Solid phase synthesis of 2-aminoquinazoline-based compounds. J Comb Chem. 2003;5:769–774.
   PubMedGoogle Scholar
• Grover RK, Kesarwani AP, Srivastava GK, et al. Base catalyzed intramolecular transamidation of 2-aminoquinazoline derivatives on solid phase. Tetrahedron. 2005;61:5011–5018.
   Web of Science ®Google Scholar
• Tran PH, Thi Bui T, Bach Lam X, et al. Synthesis of benzo[4,5]imidazo[1,2-a]pyrimidines and 2,3-dihydroquinazolin-4(1H)-ones under metal-free and solvent-free conditions for minimizing waste generation. RSC adv. 2018;8:36392–36399.
   PubMed Web of Science ®Google Scholar
• Throat VV, Katariya MV, Tekale SU, et al. Silica supported perchloric acid: an efficient and recyclable catalyst for synthesis of benzimidazolo[2,3-B]quinazolinones. Eur. Chem. Bull. 2019;8(9):313–317.
   Google Scholar
• Reddy MV, Reddy GCS, Geong YT. Molybdate sulfuric acid (MSA): an efficient reusable catalyst for the synthesis of tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolin-1(2H)-ones under solvent-free conditions and evaluation for their in vitro bioassay. RSC adv. 2015;5:11423–11432.
   Web of Science ®Google Scholar
• Zhang Y, Zhao Y, Xia C. Basic ionic liquids supported on hydroxyapatite-encapsulated γ-Fe2O3 nanocrystallites: An efficient magnetic and recyclable heterogeneous catalyst for aqueous Knoevenagel condensation. J Mol Catal A Chem. 2009;306:107–112.
   Web of Science ®Google Scholar
• Emtiazi H, Amrollahi MA, Mirjalili BBF. Nano-silica sulfuric acid as an efficient catalyst for the synthesis of substituted pyrazoles. Arab J Chem. 2015;8:793–797.
   Web of Science ®Google Scholar
• Modarresi-Alam AR, Dindarloo Inaloo I, Kleinpeter E. Synthesis of primary thiocarbamates by silica sulfuric acid as effective reagent under solid-state and solution conditions. J Mol Struc. 2012;1024:156–162.
   Web of Science ®Google Scholar
• Sardarian AR, Dindarloo Inaloo I. 4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas. RSC Adv. 2015;5(93):76626–76641.
   Web of Science ®Google Scholar
• Sardarian AR, Dindarloo Inaloo I, Modarresi-Alam AR, et al. Metal-free regioselective monocyanation of hydroxy-, alkoxy-, and benzyloxyarenes by potassium thiocyanate and silica sulfuric acid as a cyanating agent. J Org Chem. 2019;84:1748–1756.
   PubMed Web of Science ®Google Scholar
• Inaloo ID, Majnooni S. Eco-efficient ultrasonic-responsive synthesis of primary O-alkyl and O-aryl thiocarbamates using brønsted acid ionic liquid [H-NMP][HSO4] in aqueous media at room temperature. Chem Select. 2018;3(15):4095–4100.
   Google Scholar
• Zheng X, Luo S, Zhang L, et al. Magnetic nanoparticle supported ionic liquidcatalysts for CO2 cycloaddition reactions. Green Chem. 2009;11:455–458.
   Web of Science ®Google Scholar
• Marvaniya HM, Modi KN, Sen DJ. Greener reactions under solvent free conditions. Int J Drug Dev Res. 2011;3(2):42–51.
   Google Scholar
• Mondal B, Kundu M, Mandal SP, et al. Sonochemically synthesized spin-canted CuFe2O4 nanoparticles for heterogeneous green catalytic click chemistry. ACS Omega. 2019;4:13845–13852.
   PubMed Web of Science ®Google Scholar
• Kundu M, Mondal B, Das D, et al. Synthesis and reactivity of copper and copper containing magnetically separable catalysts. Sci Repor. 2022;7:e202104543.
   Google Scholar
• Sarkar BJ, Kundu M, Monal B, et al. Microstructural investigation of sonochemically synthesized Zn substituted CuFe2O4 nanoparticles for heterogeneous green catalytic click chemistry and dye degradation. J Mol Struct. 2023;1274:134493.
   Web of Science ®Google Scholar
• Nagendrappa G. Organic synthesis using clay catalysts. Reson. 2002;7:64–77.
   Google Scholar
• Debnath K, Mukherjee S, Bodhak C, et al. Facile one-pot three-component synthesis of diverse 2, 3-disubstituted isoindolin-1-ones using ZrO 2 nanoparticles as a reusable dual acid–base solid support under solvent-free conditions. RSC Adv. 2016;6:21127–21138.
   Web of Science ®Google Scholar
• Fekri LZ, Zeinali S. Copper/Schiff-base complex immobilized on amine functionalized silica mesoporous magnetic nanoparticles under solvent-free condition: A facile and new avenue for the synthesis of thiazolidin-4-ones. App Orgmet Chem. 2020;34(6):e5629.
   Web of Science ®Google Scholar
• Fekri L Z, Darya-Laal AR. Nife2o4@ SiO2@ amino glucose magnetic nanoparticle as a green, effective and magnetically separable catalyst for the synthesis of xanthene-ones under solvent-free condition. Polycycl Arom Comp. 2020;40(5):1539–1556.
   Web of Science ®Google Scholar
• Fekri LZ, Hamidian H, Chekosarani MA. Urazolium diacetate as a new,: efficient and reusable brønsted acid ionic liquid for the synthesis of novel derivatives of thiazolidine-4-ones. RSC Adv. 2020;10(1):556–564.
   PubMed Web of Science ®Google Scholar
• Torabi M, Fekri LZ, Nikpassand M. Synthesis,: characterization and application of Fe3O4@ silicapropyl@ vaniline-covalented isoniazid-copper (I) nanocomposite as a new, mild, effective and magnetically recoverable Lewis acid catalyst for the synthesis of acridines and novel azoacridines. J Mol Struct. 2022;1250:131761.
   Web of Science ®Google Scholar
• Fekri LZ. s-Proline covalented silicapropyl modified magnetic nanoparticles: synthesis,: characterization, biological and catalytic activity for the synthesis of thiazolidin-4-ones. Curr Org Synth. 2020;17(6):464–472.
   PubMed Web of Science ®Google Scholar
• Nikpassand M, Fekri LZ, Nabatzadeh M. Fe3O4@ SiO2@ KIT-6 as an efficient and reusable catalyst for the synthesis of novel derivatives of 3, 3'-((aryl-1-phenyl-1H-pyrazol-4-yl) methylene) bis (1H-indole). Comb Chem High Throughput Screen. 2017;20:533–538.
   PubMed Web of Science ®Google Scholar
• Nikpassand M, Keyhani A, Fekri LZ, et al. Mechanochemical synthesis of azo-linked 2-amino-4H-chromene derivatives using Fe3O4@ SiO2@ KIT-6-NH2@ schiff-base complex nanoparticles. J Mol Struct. 2022;1251:132065.
   Web of Science ®Google Scholar
• Shaabani A, Farhangi E, Shaabani S. A rapid combinatorial library synthesis of benzazolo [2, 1-b] quinazolinones and triazolo [2, 1-b] quinazolinones. Iran J Chem Engin. 2013;32:3–10.
   Web of Science ®Google Scholar
• Wu L, Yan F, Ch Y. Silica sulfuric acid promoted one-pot synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine derivatives under solvent-free conditions. Bull Chem Soc Ethiop. 2010;24(3):417–423.
   Web of Science ®Google Scholar