Abstract
Aurivillius nanostructures of Bi2ZnAl2O9 were biosynthesized via a green co-precipitation method using bismuth nitrate pentahydrate, zinc acetate dihydrate and aluminum acetate in the presence of ethanol amine as the precipitating agent and mulberry leaves extract as preparing the green and mild media for the reaction of catalyst synthesis. For better characterization of the obtained nanostructures of Aurivillius, Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy dispersive X-ray spectroscopy (EDX) and field emission scanning electron microscopy (FE-SEM) were applied as the characterizing techniques. In spite of the electrical, physical and photochemical applications of Aurivillius nanostructures, for the first time, perovskite-like Aurivillius nanostructures were used in the organic chemical synthesis of pyrimidines. These recyclable heterogeneous nanoparticles were applied in the one-pot Biginelli coupling reaction of beta-keto esters, different aromatic aldehydes and urea to afford the related 3,4-dihydropyrimidin-2-(1H) derivatives in good to excellent yields under solvent-free conditions at 80 °C as the optimized temperature.
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References
Wang X, Zhuang J, Peng Q, Li Y (2005) A general strategy for nanocrystal synthesis. Nature 437:121–124
Xia Y, Yang P (2003) Guest editorial: chemistry and physics of nanowires. Adv Mater 15:351–352
Pan ZW, Dai ZR, Wang ZL (2001) Nanobelts of semiconducting oxides. Science 291:1947–1949
Zhang Y-W, Sun X, Si R, You L-P, Yan C-H (2005) Single-crystalline and monodisperse LaF3 triangular nanoplates from a single-source precursor. J Am Chem Soc 127:3260–3261
Li M, Schnablegger H, Mann S (1999) Coupled synthesis and self-assembly of nanoparticles to give structures with controlled organization. Nature 402:393–395
Park S, Lim J-H, Chung S-W, Mirkin CA (2004) Self-assembly of mesoscopic metal-polymer amphiphiles. Science 303:348–351
Liu B, Zeng HC (2004) Mesoscale organization of CuO nanoribbons: formation of “dandelions”. J Am Chem Soc 126:8124–8125
Zhang T, Dong W, Keeter-Brewer M, Konar S, Njabon RN, Tian ZR (2006) Site-specific nucleation and growth kinetics in hierarchical nanosyntheses of branched ZnO crystallites. J Am Chem Soc 128:10960–10968
Wachsmuth B, Zschech E, Thomas N, Brodie S, Gurman S, Baker S, Bayliss S (1993) Structure model of Aurivillius compounds. An EXAFS study. Physi Status Solidi A 135:59–71
Mitchell RH (2002) Perovskites: modern and ancient, vol 3. Almaz Press, Thunder Bay
Zhu J, Bienaymé H (2005) Multicomponent Reactions. Wiley-VCH, Weinheim
Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA (1996) Multiple-component condensation strategies for combinatorial library synthesis. Accounts Chem Res 29:123–131
Tietze LF, Modi A (2000) Multicomponent domino reactions for the synthesis of biologically active natural products and drugs. Med Res Rev 20:304–322
Dömling A (2002) Recent advances in isocyanide-based multicomponent chemistry. Curr Opin Chem Biol 6:306–313
Weber L (2002) Multi-component reactions and evolutionary chemistry. Drug Discov Today 7:143–147
Ugi I, Heck S (2001) The multicomponent reactions and their libraries for natural and preparative chemistry. Comb Chem High T Scr 4:1–34
Bannwarth W, Hinzen B, Mannhold R, Kubinyi H, Folkers G (2006) Combinatorial chemistry: From theory to application. Wiley, Hoboken
Volochnyuk DM, Ryabukhin SV, Plaskon AS, Grygorenko OO (2009) Organosilicon compounds as water scavengers in reactions of carbonyl compounds. Synthesis 2009:3719–3743
Ryabukhin SV, Plaskon AS, Ostapchuk EN, Volochnyuk DM, Shishkin OV, Shivanyuk AN, Tolmachev AA (2007) A one-step fusion of 1, 3-thiazine and pyrimidine cycles. Org Lett 9:4215–4218
Ryabukhin SV, Plaskon AS, Ostapchuk EN, Volochnyuk DM, Shishkin OV, Tolmachev AA (2008) CF 3-substituted 1, 3-dicarbonyl compounds in the Biginelli reaction promoted by chlorotrimethylsilane. J Fluorine Chem 129:625–631
Zhu Y, Pan Y, Huang S (2004) Trimethylsilyl chloride: a facile and efficient reagent for one-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones. Synthetic Commun 34:3167–3174
Foroughifar N, Mobinikhaledi A, FathinejadJirandehi H (2003) Microwave assisted synthesis of some pyrimidine derivatives using polyphosphate ester (PPE) in ceramic bath. Phosphorus Sulfur 178:1241–1246
Kappe CO (2000) Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Accounts Chem Res 33:879–888
Ma Y, Qian C, Wang L, Yang M (2000) Lanthanide triflate catalyzed Biginelli reaction. One-Pot synthesis of dihydropyrimidinones under solvent-free conditions. J Org Chem 65:3864–3868
Hu EH, Sidler DR, Dolling U-H (1998) Unprecedented catalytic three component one-pot condensation reaction: an efficient synthesis of 5-alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)-ones. J Org Chem 63:3454–3457
Wang Z-T, Xu L-W, Xia C-G, Wang H-Q (2004) Novel Biginelli-like three-component cyclocondensation reaction: efficient synthesis of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett 45:7951–7953
Maiti G, Kundu P, Guin C (2003) One-pot synthesis of dihydropyrimidinones catalysed by lithium bromide: an improved procedure for the Biginelli reaction. Tetrahedron Lett 44:2757–2758
Reddy CV, Mahesh M, Raju PVK, Babu TR, Reddy VVN (2002) Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett 43:2657–2659
Ramalinga K, Vijayalakshmi P, Kaimal TNB (2001) Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction. Synlett 2001:0863–0865
Ananda Kumar K, Kasthuraiah M, Suresh Reddy C, Devendranath Reddy C (2001) Mn(OAc)3·2H2O-mediated three-component, one-pot, condensation reaction: an efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2-ones. Tetrahedron Lett 42:7873–7875
Lu J, Bai Y, Wang Z, Yang B, Ma H (2000) One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst. Tetrahedron Lett 41:9075–9078
Ranu BC, Hajra A, Jana U (2000) Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the Biginelli reaction. J Org Chem 65:6270–6272
Paraskar AS, Dewkar GK, Sudalai A (2003) Cu(OTf)2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett 44:3305–3308
Ghosh R, Maiti S, Chakraborty A (2004) In(OTf)3-catalysed one-pot synthesis of 3,4-dihydropyrimidin-2(lH)-ones. J Mol Catal A: Chem 217:47–50
Sun Q, Y-q Wang, Z-m Ge, T-m Cheng, R-t Li (2004) A highly efficient solvent-free synthesis of dihydropyrimidinones catalyzed by zinc chloride. Synthesis 2004:1047–1051
Lu J, Bai Y (2002) Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Synthesis 2002:0466–0470
Salehi H, Guo QX (2004) A facile and efficient one-pot synthesis of dihydropyrimidinones catalyzed by magnesium bromide under solvent-free conditions. Synthetic Commun 34:171–179
Bose DS, Fatima L, Mereyala HB (2003) Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4- dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction: comparison of ethanol, water, and solvent-free conditions. J Org Chem 68:587–590
Su W, Li J, Zheng Z, Shen Y (2005) One-pot synthesis of dihydropyrimidiones catalyzed by strontium(II) triflate under solvent-free conditions. Tetrahedron Lett 46:6037–6040
Shirini F, Zolfigol M, Abri A-R (2008) Fe (HSO4)3 as an efficient catalyst for the preparation of 3,4-dihydropyrimidin-2 (1H)-ones in solution and under solvent-free conditions. J Iran Chem Soc 5:96–99
Mobinikhaledi A, Foroughifar N, Khajeh-Amiri A (2016) N-Propylcarbamothioyl benzamide complex of Bi(III) supported on superparamagnetic Fe3O4/SiO2 nanoparticles as a highly efficient and magnetically recoverable heterogeneous nanocatalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2 (1H)-ones/thiones (DHPMs) via the Biginelli reaction. React Kinet Catal 117:59–75
Litvić M, Večenaj I, Ladišić ZM, Lovrić M, Vinković V, Filipan-Litvić M (2010) First application of hexaaquaaluminium(III) tetrafluoroborate as a mild, recyclable, non-hygroscopic acid catalyst in organic synthesis: a simple and efficient protocol for the multigram scale synthesis of 3,4-dihydropyrimidinones by Biginelli reaction. Tetrahedron 66:3463–3471
Kolosov MA, Orlov VD, Beloborodov DA, Dotsenko VV (2008) A chemical placebo: NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis. Mol Divers 13:5–25
Gross WL, Hellmich B (2003) Arteriitis temporalis Horton (Riesenzellarteriitis) (Giant cell arteritis). Dtsch Med Wochenschr 128:2604–2607
Foroughifar N, Mobinikhaledi A, Rabeie B, Jalili L (2013) DABCO as a mild and efficient catalyst for the synthesis of tetrahydropyrimidines. Rev Roum Chim 58:491–495
Polshettiwar V, Varma RS (2007) Biginelli reaction in aqueous medium: a greener and sustainable approach to substituted 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett 48:7343–7346
Kidwai M, Mohan R (2005) Green chemistry: an innovative technology. Found Chem 7:269–287
Hegedüs A, Hell Z, Potor AA (2005) simple environmentally-friendly method for the selective synthesis of 1,5-benzodiazepine derivatives using zeolite catalyst. Catal Lett 105:229–232
Salehi P, Dabiri M, Zolfigol MA, Fard MAB (2003) Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2 (1H)-ones. Tetrahedron Lett 44:2889–2891
Mobinikhaledi A, Yazdanipour A, Ghashang M (2015) Green synthesis of 2-amino-7-hydroxy-4-aryl-4H -chromene-3-carbonitriles using ZnO nanoparticles prepared with mulberry leaf extract and ZnCl2. Turk J Chem 39:667–675
Acknowledgments
We are grateful to the Arak University research council for partial support of this research. Also the authors wish to thank Ms Somayeh Veyseh for her valuable help in this study for characterization of FE-SEM, EDX and XRD.
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Mobinikhaledi, A., Yazdanipour, A. & Ghashang, M. A green one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by novel Aurivillius nanostructures under solvent-free conditions. Reac Kinet Mech Cat 119, 511–522 (2016). https://doi.org/10.1007/s11144-016-1053-2
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DOI: https://doi.org/10.1007/s11144-016-1053-2