Application of $$\hbox {SiO}_{{2}}$$ nanoparticles as an efficient catalyst to develop syntheses of perimidines and tetraketones

Heshmatollah Alinezhad1, Armin Ahmadi1, Parvin Hajiabbasi1
1Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran

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