Document Type : Note
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
Silica boron sulfonic acid [SiO2–B(OSO3H)3] as an inexpensive, reusable, and Lewis and Brønsted acid catalyst was successfully synthesized, and used for the one-pot three-components synthesis of biologically active substituted Hantzsch 1,4-dihydropyridine derivatives in the absence of solvent at 90ºC. Silica boron sulfonic acid is attractive and efficient, because it plays in two role as a Lewis acid (by boron atom) and also as a Brønsted acid (by OSO3H group), which can have a better effect in reaction. The reaction was carried out under solvent-free and mild conditions. Silica boron sulfonic acid can be recovered and reused for at least five consecutive runs.
- Hajinasiri R., and Rezayati S. Solvent-free synthesis of 1,2-disubstituted derivatives of 1,2-dihydroisoquinoline, 1,2-dihydroquinoline and 1,2-dihydropyridine. Z. Naturforsch.,68b: 818–822 (2013).
- Shaabani A., Maleki A., Rezayan A.H., and Sarvary A. Recent progress of isocyanide-based multicomponent reactions in iran. Mol. Divers.,15: 41–68 (2011).
- Balme G., Bossharth E., and Monteiro N. Pd-assisted multicomponent synthesis of heterocycles. Eur. J. Org. Chem., 2003: 4101–4111 (2003).
- Fewell S.W., Smith C.M., Lyon M.A., Dumitrescu T.P., Wipf P., Day B.W., and Brodsky J.L. Small molecule modulators of endogenous and co-chaperone-stimulated hsp70 ATPase activity. J. Biol. Chem., 279: 51131–51140 (2004).
- Lou S., Taoka B.M., Ting A., and Schaus S.E. Asymmetric mannich reactions of β-keto esters with acyl imines catalyzed by cinchona alkaloids. J. Am. Chem. Soc., 127: 11256–11257 (2005).
- Chebanov V.A., Muravyova E.A., Desenko S.M., Musatov V.I., Knyazeva I.V., Shishkina S.V., Shishkin O.V., Kappe C.O. Microwave-assisted three component synthesis of 7-aryl-2-alkylthio-4,7-dihydro-1,2,4-triazolo[1,5-a]-pyrimidine-6-carboxamides and their selective reduction. J. Comb. Chem., 8: 427–434 (2006).
- Xu L.W., Xia C.G., Li L. Transition metal salt-catalyzed direct three-component mannich reactions of aldehydes, ketones, and carbamates: Efficient synthesis of N-protected β-aryl-β-amino ketone compounds. J. Org. Chem., 69: 8482–8484 (2004).
- Hantzsch A. Condensation product aus aldehydammoniak und ketonartigen verbindungen. Ber. Dtsch. Chem. Ges., 14: 1637–1638 (1881).
- Bretzel R.G., Bollen C.C., Maeser E., and Federlin K.F. Nephroprotective effects of nitrendipine in hypertensive tune I and type II diabetic patients. Am. J. Kidney. Dis., 21: 53–64 (1993).
- Pastan I., Gottesman M.M. Multiple-drug resistance in human cancer. N. Engl. J. Med., 316: 1388–1393 (1987).
- Love B., and Snader K.M. The hantzsch reaction. I. Oxidative dealkylation of certain dihydropyridines. J. Org. Chem., 30: 1914–1916 (1965).
- Tuttle J.B., Ouellet S.G., and MacMillan D.W. Organocatalytic transfer hydrogenation of cyclic enones. J. Am. Chem. Soc., 128: 12662–12663 (2006).
- Sapkal S.B., Shelke K.F., Shingate B.B., and Shingare M. Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via hantzsch condensation under solvent-free conditions. Tetrahedron Lett., 50: 1754–1756 (2009).
- Kolvari E., Zolfigol M.A., Koukabi N., and Shirmardi-Shaghasemi B. A simple and efficient one-pot synthesis of hantzsch 1,4-dihydropyridines using silica sulphuric acid as a heterogeneous and reusable catalyst under solvent-free conditions. Chem. Pap., 65: 898–902 (2011).
- Debache A., Ghalem W., Boulcina R., Belfaitah A., Rhouati S., and Carboni B. An efficient one-step synthesis of 1,4-dihydropyridines via a triphenylphosphine-catalyzed three-component hantzsch reaction under mild conditions. Tetrahedron Lett., 50: 5248–5250 (2009).
- Jahanbin B., Davoodnia A., Behmadi H., and Tavakoli-Hoseini N. Polymer support immobilized acidic ionic liquid: Preparation and its application as catalyst in the synthesis of hantzsch 1,4-dihydropyridines. Bull. Korean Chem. Soc., 33: 2140–2144 (2012).
- Reddy C.S., and Raghu M. Cerium(IV) ammonium nitrate catalysed facile and efficient synthesis of polyhydroquinoline derivatives through hantzsch multicomponent condensation. Chin. Chem. Lett., 19: 775–779 (2008).
- Sabitha G., Reddy G.S.K., Reddy C.S., and Yadav J.S. A novel TMSI-mediated synthesis of hantzsch 1,4-dihydropyridines at ambient temperature. Tetrahedron Lett., 44: 4129–4131 (2003).
- Ko S., Sastry M.N.V., Lin C., and Yao C.F. Molecular iodine-catalyzed one-pot synthesis of 4-substituted-1,4-dihydropyridine derivatives via hantzsch reaction. Tetrahedron Lett., 46: 5771–5774 (2005).
- Sajjadifar S., Saeidian H., Zare S., Veisi H., and Rezayati S. Hantzsch reaction using [Mesi]Cl as a new, efficient and BAIL catalyst. Iran. Chem. Commun., 1: 4-13 (2013).
- Hong M., Cai C., and Yi W.B. Hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed synthesis of polyhydroquinoline derivatives via unsymmetrical hantzsch reaction in fluorous medium. J. Fluorine Chem., 131: 111–114 (2010).
- Wang L.M., Sheng J., Zhang L., Han J.W., Fan Z.Y., Tiana H., and Qian C.T. Facile Yb(OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives through hantzsch reaction. Tetrahedron, 61: 1539–1543 (2005).
- Nasr-Esfahani M., Hoseini S.J., Montazerozohori M., Mehrabi R., and Nasrabadi H. Magnetic Fe3O4 nanoparticles: Efficient and recoverable nanocatalyst for the synthesis of polyhydroquinolines and hantzsch 1,4-dihydropyridines under solvent-free conditions. J. Mol. Catal. A. Chem., 382: 99–105 (2014).
- Kumar S., Sharma P., Kapoor K.K., and Hundal M.S. An efficient, catalyst- and solvent-free, four-component, and one-pot synthesis of polyhydroquinolines on grinding. Tetrahedron, 64: 536–542
- Arsalan M., Faydali C., Zengin M., Kucukislamoglum., and Demirhan H. An efficient one pot synthesis of 1,4-dihydropyridines using alumina sulfuric acid (ASA) catalyst. Turk. J. Chem., 33: 769–774 (2009).
- Singh S.K., and Singh K.N. Glycine-catalyzed easy and efficient one-pot synthesis of polyhydroquinolines through hantzsch multicomponent condensation under controlled microwave. J. Heterocycl Chem., 47: 194–198 (2010).
- Rezayati S., and Javanmardi P. Phospho sulfonic acid: an efficient solid acid catalyst for the facile preparation of 1,4-dihydropyridines. Iran. J. Catal., 5: 123-127 (2015).
- Mekheimer R.A., Hameed A.A., and Sadek K.U. Solar thermochemical reactions: four-component synthesis of polyhydroquinoline derivatives induced by solar thermal energy. Green Chem., 10: 592–593 (2008).
- Sufirez M., Ochoa E., Verdecia Y., Verdecia B., Moran L., Martin N., Quinteiro M., Seoane C., Soto J.L., Novoa H., Blaton N., and Peters O.M. A joint experimental and theoretical structural study of novel substituted 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines. Tetrahedron, 55: 875–884 (1999).
- Bandyopadhyay D., Maldonado S., and Banik B.K. A microwave-assisted bismuth nitrate-catalyzed unique route toward 1,4-dihydropyridines. Molecules, 17: 2643-2662 (2012).
- Kiasat A.R., and Fallah-Mehrjardi M. B(HSO4)3: A novel and efficient solid acid catalyst for the regioselective conversion of epoxides to thiocyanohydrins under solvent-free conditions. J. Braz. Chem. Soc., 19: 1595-1599 (2008).
- Sajjadifar S., and Rezayati S. Synthesis of 1,1-diacetates catalysed by silica-supported boron sulfonic acid under solvent-free conditions and ambient temperature. Chem. Pap., 68: 531–539 (2014).
- Rezayati S., and Sajjadifar S. Recyclable boron sulfonic acid as an environmentally benign catalyst for the one-pot synthesis of coumarin derivatives under solvent-Free condition. J. Sci. I. R. Iran., 25: 329-337 (2014).
- Abbasi Z., Rezayati S., Bagheri M., and Hajinasiri R. Preparation of a novel, efficient, and recyclable magnetic catalyst, γ-Fe2O3@HAp-Ag nanoparticles, and a solvent- and halogen-free protocol for the synthesis of coumarin derivatives. Chin. Chem. Lett., 28: 75–82 (2017).
- Sajjadifar S., Mirshokraie S.A., Javaherneshan N., and Louie O. SBSA as a New and efficient catalyst for the one-pot green synthesis of benzimidazole derivatives at room temperature. Am. J. Org. Chem., 2: 1-6 (2012).
- Zolfigol M.A., Khazaei A., Vahedi H., Mokhlesi M., Sajjadifar S., and Pirveysian M. Heterogeneous and catalytic thiocyanation of aromatic compounds in aqueous media. Phosphorus, Sulfur, and Silicon., 187: 295-304 (2012).
- Mosslemin M.H., and Eshaghi Movahed A. B(HSO4)3 as an efficient catalyst for the syntheses of bis(1H-Indol-3-yl)ethanones and bis(benzotriazol-1-yl)ethanones. J. Chem., 9: 301-307 (2012).
- Madje B.R., Ubale M.B., Bharad J.V., and Shingare M.S. B(HSO4)3: an efficient solid acid catalyst for the synthesis of anthraquinone derivatives. Bulletin of the Catalysis Society of India. 9: 19-25 (2011).
- Sedighinia E., and Zahed Sargoli M. Silica chloride and boron sulfonic acid as solid acid catalysts in preparation of ethers and esters under solvent-free condition. Asian. J. Chem., 23: 1456-1458 (2012).
- Karimi-Jaberi Z., and Pooladian B. A mild, efficient, and environmentally friendly synthesis of N, N′-arylidene bisamides using B (HSO4)3 under solvent-free conditions. Monatsh. Chem., 144: 659–663 (2013).
- Moghanian H., Mobinikhaledi A., and Deinavizadeh M. Efficient, one-pot synthesis of xanthene derivatives using boron sulphonic acid as a solid heterogeneous catalyst under solvent-free conditions. Res. Chem. Intermed., 41: 4387–4394 (2015).
- Dutta P., and Borah R. Boron sulfonic acid (BSA) catalyzed selective synthesis of aryl-bis(2- hydroxynaphth-1-yl)methanes and 14-alkyl- and 14-aryl-14H-dibenzoxanthenes under solvent-free condition. Cur. Chem. Lett., 4: 93–100 (2015).