Application of $$\hbox {SiO}_{{2}}$$ nanoparticles as an efficient catalyst to develop syntheses of perimidines and tetraketones
Tóm tắt
In this paper, we explore the catalytic activity of
$$\hbox {SiO}_{{2}}$$
nanoparticles (NPs) as an eco-friendly, efficient and reusable catalyst in the synthesis of 2,3-dihydro-1H-perimidines as well as tetraketones. For tetraketones syntheses, a simple tandem Knoevenagel condensation following Michael addition procedure is performed by the reaction between benzaldehydes and 5,5-dimethyl-1,3-cyclohexanediones under solvent-free condition using
$$\hbox {SiO}_{{2}}$$
NPs as an efficient solid catalyst. In addition, for 2,3-dihydro-1H-perimidines syntheses, cyclocondensation of various aldehydes with 1,8-diaminonaphthalene is achieved under solvent-free condition using
$$\hbox {SiO}_{{2}}$$
NPs as a catalyst at room temperature. The results showed catalytic enhancement in both synthetic procedures. In this work, 4-(2,3-dihydro-1H-perimidin-2-yl)benzonitrile and 2-(pyridin-4-yl)-2,3-dihydro-1H-perimidine are synthesized as new compounds. Also, reusability study of
$$\hbox {SiO}_{{2}}$$
NPs was done to ensure its applicability as a recycled catalyst in this work. The catalytic activity of
$$\hbox {SiO}_{{2}}$$
nanoparticles (NPs) as an eco-friendly, efficient and reusable catalyst in the synthesis of 2,3-dihydro-1H-perimidines as well as tetraketones is explored. For tetraketones syntheses, a simple tandem Knoevenagel condensation following Michael addition procedure is performed by the reaction between benzaldehydes and 5,5-dimethyl-1,3-cyclohexanediones under solvent-free condition using
$$\hbox {SiO}_{{2}}$$
NPs as an efficient solid catalyst.
Tài liệu tham khảo
Gellermann C, Storch W and Wolter H 1997 Synthesis and characterization of the organic surface modifications of monodisperse colloidal silica J. Sol-Gel Sci. Tech. 8 173
Van Cantfort O, Michaux B, Pirard R, Pirard J P and Lecloux A J 1997 Synthesis and characterization of monodisperse spherical zirconia particles J. Sol-Gel Sci. Tech. 8 207
Ishida H, Tadanaga K, Hayashi A and Tatsumisago M 2013 Synthesis of monodispersed lithium silicate particles using the sol-gel method J. Sol-Gel Sci. Tech. 65 41
Guan H, Chao C, Lu Y, Shang H, Zhao Y, Yuan S and Zhang B 2016 PtNi nanoparticles embedded in porous silica microspheres as highly active catalysts for p-nitrophenol hydrogenation to p-aminophenol J. Chem. Sci. 128 1355
Baharfar R and Azimi R 2015 Sulfanilic acid functionalized mesoporous SBA-15: A water-tolerant solid acid catalyst for the synthesis of uracil fused spirooxindoles as antioxidant agents J. Chem. Sci. 127 1389
Niknam Kh and Abolpour P 2015 Synthesis of naphthoxazinone derivatives using silica-bonded \(S\)-sulfonic acid as catalyst under solvent-free conditions J. Chem. Sci. 127 1315
Nguyen V, Chan H and Wu J C S 2013 Synthesis, characterization and photo-epoxidation performance of Au-loaded photocatalysts J. Chem. Sci. 125 859
Safaei-Ghomi J, Ziarati A and Zahedi S 2012 Silica (NPs) supported Fe (III) as a reusable heterogeneous catalyst for the one-pot synthesis of 1,4-dihydropyridines under mild conditions J. Chem. Sci. 124 933
Zolfigol M A, Khazaei A, Zare A, Mokhlesi M, Hekmat-Zadeh T, Hasaninejad A, Derakhshan-Panah F, Moosavi-Zare A R, Keypour H, Dehghani-Firouzabadid A A and Merajoddin M 2012 Solid-supported sulfonic acid-containing catalysts efficiently promoted one-pot multi-component synthesis of \(\beta \)-acetamido carbonyl compounds J. Chem. Sci. 124 501
Bu X, Deady L W, Finlay G J, Baguley B C and Denny W A 2001 Synthesis and cytotoxic activity of 7-oxo-7\(H\)-dibenz[\(f\),ij]isoquinoline and 7-oxo-7\(H\)-benzo[\(e\)]perimidine derivatives J. Med. Chem. 44 2004
Mobinikhaledi A, Amrollahi M A, Foroughifar N and Fathinejad H 2005 Microwave assisted synthesis of some 2-alkyl and 2-arylperimidines Asian J. Chem. 17 2411
Phadtare S, Ranganathan V and Shankarling G 2012 Efficient synthesis of 2,3-dihydro-1\(H\)-perimidine derivatives using HBOB as a novel solid acid catalyst Aust. J. Chem. 65 86
Shanmugasundram P, Prabahar K J and Ramakrishnan V T 1993 A new class of laser dyes from acridinedione derivatives J. Heterocycl. Chem. 30 1003
Shanmugasundram P, Murugan P, Ramakrishnan V T, Srividya N and Ramamurthy P 1996 Synthesis of acridinedione derivatives as laser dyes Heteroatom Chem. 7 17
Sivaraman K, Subramanian K, Ganesan S and Ramakrishnan V T 1995 Spectroscopic studies on the interaction of three partially hydrogenated acridine dyes with calf thymus DNA and their structural comparison J. Biomol. Struct. Dyn. 13 119
Timpe H J and Ulrich S Ali 1991 Spin-trapping as a tool for quantum yield determinations in radical forming processes J. Photochem. Photobiol. \(A\) 61 77
Timpe H J, Ulrich S and Fouassier J P 1993 Photochemistry and use of decahydroacridine-1, 8-diones as photosensitizers for onium salt decomposition J. Photochem. Photobiol. A 73 139
Ulrich S, Timpe H J, Fouassier J P and Savary F M 1993 Photoreduction of decahydroacridine-1,8-diones by amines J. Photochem. Photobiol. A 74 165
Timpe H J, Ulrich S, Decker C and Fouassier J P 1993 Photoinitiated polymerization of acrylates and methacrylates with decahydroacridine-1,8-dione/onium salt initiator systems Macromolecules 26 4560
Ren Z, Cao W, Tong W and Jing X 2002 Knoevenagel condensation of aldehydes with cyclic active methylene compounds in water Synth. Commun. 32 1947
Karimi Rad F and K. Behbahani F 2017 Tetraketones, Synthesis and their Applications Curr. Org. Chem. 14 22
Safaei-Ghomi J, Asadian S, Nazemzadeh S H and Shahbazi-Alavi H 2017 Synthesis of tetraketones using ZnS nanoparticles as an efficient catalyst J. Chin. Chem. Soc. 65 430
Alam M and Lee D -U 2016 Synthesis, spectroscopic and computational studies of 2-(thiophen-2-yl)-2,3-dihydro-1\(H\)-perimidine: An enzymes inhibition study Comput. Biol. Chem. 64 185
Tajbakhsh M, Kariminasab M, Alinezhad H, Hosseinzadeh R, Rezaee P, Tajbakhsh M, Gazvini H J and Amiri M A 2015 Nano silica-bonded aminoethylpiperazine: a highly efficient and reusable heterogeneous catalyst for the synthesis of 4\(H\)-chromene and 12\(H\)-chromeno[2,3-\(d\)]pyrimidine derivatives J. Iran. Chem. Soc. 12 1405
Mehrasbi E, Sarrafi Y, Vahid A and Alinezhad H 2015 Sulfonic acid-functionalized mesoporous silica nanoparticles (SAMSNs): a recoverable heterogeneous acid catalyst for green synthesis of dicoumarols Res. Chem. Intermed. 41 4929
Alinezhad H, Tajbakhsh M and Ghobadi N 2015 Nano-\(\text{ Fe }_{{3}}\text{ O }_{{4}}\)-supported, hydrogensulfate ionic liquid-catalyzed, one-pot synthesis of polysubstituted pyridines Synth. Commun. 45 1964
Baharfar R, Alinezhad H and Azimi R 2015 Use of DABCO-functionalized mesoporous SBA-15 as catalyst for efficient synthesis of kojic acid derivatives, potential antioxidants Res. Chem. Intermed. 41 8637
Mobinikhaledi A, Moghanian H and Sasani F 2010 A simple and convenient Method for the synthesis of perimidine derivatives catalyzed by nano-silica sulfuric acid Int. J. Green Nanotech. 2 47
Mobinikhaledi A, Bodaghi Fard M A, Sasani F and Amrollahi M A 2013 Molecular iodine catalyzed synthesis of some biologically active dihydroperimidines Bulg. Chem. Commun. 45 353
Shi D, Wang Y, Lu Z and Dai G 2000 Condensation of aromatic aldehydes with acidic methylene compounds without catalyst Synth. Commun. 30 713
Kameshwara R V, Manoj K M and Anil K 2011 An efficient and simple synthesis of tetraketones catalyzed by Yb(OTf)\(_{3}\)-\(\text{ SiO }_{{2}}\) under solvent free condition Indian J. Chem. 50 1128
Yu J, Wang L, Liu J, Guo F, Liu Y and Jiao N 2010 Synthesis of tetraketones in water and under catalyst-free conditions Green Chem. 12 216
Farrokhi A, Ghodrati K and Yavari I 2015 \(\text{ Fe }_{{3}}\text{ O }_{{4}}\)/\(\text{ SiO }_{{2}}\)/\((\text{ CH }_{2})_{3}\text{ N }^{+}\text{ Me }_{{3}}\text{ Br }_{{3}}^{-}\) core-shell nanoparticles: A novel catalyst for the solvent-free synthesis of five- and six-membered heterocycles Catal. Commun. 63 41
Korani E, Ghodrati K and Asnaashari M 2018 Magnetic core-shell nanoparticles containing \(\text{ I }_{{3}}^{-}\) as a novel catalyst for the facile synthesis of imidazole, thiazole and pyrimidine derivatives in solvent-free conditions Silicon 10 1433
Amrollahi M A and Vahidnia F 2018 Decoration of \(\beta \)-CD-ZrO on \(\text{ Fe }_{{3}}\text{ O }_{{4}}\) magnetic nanoparticles as a magnetically, recoverable and reusable catalyst for the synthesis of 2,3-dihydro-1\(H\)-perimidines Res. Chem. Intermed. 44 7569
Mobinikhaledi A, Foroughifar N and Basaki N 2009 Zeolite catalyzed efficient synthesis of perimidines at room temperature Turk. J. Chem. 33 555
Kantevari S, Bantu R and Nagarapu L 2007 \(\text{ HClO }_{{4}}\)-\(\text{ SiO }_{{2}}\) and PPA-\(\text{ SiO }_{{2}}\) catalyzed efficient one-pot Knoevenagel condensation, Michael addition and cyclo-dehydration of dimedone and aldehydes in acetonitrile, aqueous and solvent free conditions: Scope and limitations J. Mol. Catal. A 269 53
Naka Y, Komori Y and Yoshitake H 2010 One-pot synthesis of organo-functionalized monodisperse silica particles in W/O microemulsion and the effect of functional groups on addition into polystyrene Colloids Surf. A 361 162
Alinezhad H and Zare M 2013 Sulfonated ordered nanoporous carbon as an efficient solid catalyst for the synthesis of perimidine derivatives J. Chil. Chem. Soc. 58 1840