Synthesis and characterization of sodium polyaspartate-functionalized silica-coated magnetite nanoparticles: A heterogeneous, reusable and magnetically separable catalyst for the solvent-free synthesis of 2-amino-4H-chromene derivatives

An efficient and facile method was used for the synthesis of sodium polyaspartate-functionalized silica-coated magnetite nanoparticles. The structure of this nanoparticle was characterized by scanning electron microscopies, X-ray diffraction, energy-dispersive X-ray, Fourier transform infrared spectroscopies and vibrating sample magnetometry. Then, this compound was used as a reusable heterogeneous catalyst for green synthesis of 2-amino-4H-chromene derivatives via one-pot three-component reactions. This novel material showed great catalytic performance and the reactions which were carried out by this catalyst showed good to excellent yields. Besides, the catalyst could easily be separated from the reaction mixture by using an external magnetic field and it was stable enough to reuse several times without any significant reduction in the yield of reactions. Eco-friendliness, high purity of the desired products, short reaction time and easy workup procedure can be mentioned as the other advantages of this method.

[1]  P. Ritprajak,et al.  Size-dependent cytotoxicity and inflammatory responses of PEGylated silica-iron oxide nanocomposite size series , 2017 .

[2]  Saleheh Zavar.  A novel three component synthesis of 2-amino-4H-chromenes derivatives using nano ZnO catalyst , 2017 .

[3]  B. G. Mishra,et al.  CaO-ZrO2 nanocomposite oxide prepared by urea hydrolysis method as heterogeneous base catalyst for synthesis of chromene analogues , 2016 .

[4]  B. Notash,et al.  Synthesis, structural characterization, X-ray, solvatochromism and biological properties of 7-hydroxy-2-(2-hydroxy-5-(phenyldiazenyl)benzylidene)amino)-4-phenyl-4H-chromene-3-carbonitrile , 2016 .

[5]  Monika Gupta,et al.  One-pot synthesis of various 2-amino-4H-chromene derivatives using a highly active supported ionic liquid catalyst , 2016 .

[6]  Ruslan F. Nasybullin,et al.  Pseudo four-component reaction of salicylaldehydes and cyclic ketones with two molecules of malononitrile: A facile and efficient way to synthesize 4-[2-(dicyanomethylene)cyclic or heterocyclic]-2-amino-4H-chromenes , 2016 .

[7]  Bo Wu,et al.  C-H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes. , 2015, Organic letters.

[8]  B. Maleki,et al.  Zn( L‐proline)2 as a powerful and reusable organometallic catalyst for the very fast synthesis of 2‐amino‐4H‐benzo[g]chromene derivatives under solvent‐free conditions , 2015 .

[9]  M. Entezari,et al.  Amino-functionalized silica magnetite nanoparticles for the simultaneous removal of pollutants from aqueous solution , 2015 .

[10]  Liyan Jiang,et al.  A green and one-pot synthesis of benzo[g]chromene derivatives through a multi-component reaction catalyzed by lipase , 2015 .

[11]  M. Eslami,et al.  Highly efficient organocatalytic synthesis of diverse and densely functionalized 2-amino-3-cyano-4H-pyrans under mechanochemical ball milling , 2014 .

[12]  Banoth Paplal,et al.  Recyclable Bi2WO6-nanoparticle mediated one-pot multicomponent reactions in aqueous medium at room temperature , 2014 .

[13]  G. Kaupp,et al.  Ball milling for the quantitative and specific solvent-free Knoevenagel condensation + Michael addition cascade in the synthesis of various 2-amino-4-aryl-3-cyano-4H-chromenes without heating , 2014 .

[14]  B. Maleki,et al.  Nano α-Al2O3 supported ammonium dihydrogen phosphate (NH4H2PO4/Al2O3): preparation, characterization and its application as a novel and heterogeneous catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives , 2014 .

[15]  Ghodsi Mohammadi Ziarani,et al.  Silica functionalized propyl sulfonic acid (SiO2-Pr-SO3H): An efficient catalyst in organic reactions , 2014 .

[16]  M. Zolfigol,et al.  Tandem Knoevenagel–Michael–cyclocondensation reaction of malononitrile, various aldehydes and 2-naphthol over acetic acid functionalized ionic liquid , 2014 .

[17]  A. Mobinikhaledi,et al.  Efficient Synthesis of 2-amino-4H-chromene Derivatives in the Presence of Piperazine-functionalized Fe 3 O 4 /SiO 2 Magnetic Nanoparticles as a New Heterogeneous Reusable Catalyst Under Solvent-free Conditions , 2014 .

[18]  A. Mobinikhaledi,et al.  Sulfanilic acid-functionalized silica-coated magnetite nanoparticles as an efficient, reusable and magnetically separable catalyst for the solvent-free synthesis of 1-amido- and 1-aminoalkyl-2-naphthols , 2014 .

[19]  M. Zolfigol,et al.  Tandem Knoevenagel–Michael-cyclocondensation reactions of malononitrile, various aldehydes and dimedone using acetic acid functionalized ionic liquid , 2014 .

[20]  B. Banerjee,et al.  Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-cyano-4H-pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst , 2014 .

[21]  A. Bhaumik,et al.  Heterogeneous ditopic ZnFe2O4 catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester , 2014 .

[22]  Yanglong Hou,et al.  Pristine organo-imido polyoxometalates as an anode for lithium ion batteries , 2014 .

[23]  A. Kiasat,et al.  Covalently anchored n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride on SBA-15 as a basic nanocatalyst for the synthesis of pyran heterocyclic compounds , 2014 .

[24]  B. Karami,et al.  Silica tungstic acid as an efficient and reusable catalyst for the one-pot synthesis of 2-amino-4H-chromene derivatives. , 2014, Acta chimica Slovenica.

[25]  H. Tashakkorian,et al.  Nanozeolite clinoptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino-4H-chromene derivatives in aqueous media , 2013 .

[26]  Hong-Xia Liu,et al.  Meglumine: A novel and efficient catalyst for one-pot, three-component combinatorial synthesis of functionalized 2-amino-4H-pyrans. , 2013, ACS combinatorial science.

[27]  K. Niknam,et al.  Silica-bonded N-propylpiperazine sodium n-propionate as recyclable catalyst for synthesis of 4H-pyran derivatives , 2013 .

[28]  Aniruddha Molla,et al.  Multicomponent domino reactions: borax catalyzed synthesis of highly functionalised pyran-annulated heterocycles , 2013 .

[29]  A. Kiasat,et al.  Nano magnetic double-charged diazoniabicyclo[2.2.2]octane dichloride silica hybrid: Synthesis, characterization, and application as an efficient and reusable organic–inorganic hybrid silica with ionic liquid framework for one-pot synthesis of pyran annulated heterocyclic compounds in water , 2013 .

[30]  R. Varma,et al.  Nano-magnetite (Fe3O4) as a support for recyclable catalysts in the development of sustainable methodologies. , 2013, Chemical Society reviews.

[31]  Guodong Yin,et al.  Catalyst-free C–S/C–O bond formation: synthesis of novel 4-thio-substituted 2-aryl-4H-chromenes from easily available 2-hydroxychalcones , 2013 .

[32]  J. Albadi,et al.  Poly(4-vinylpyridine): As a green, efficient and commercial available basic catalyst for the synthesis of chromene derivatives , 2013 .

[33]  Rajashri S. Salunkhe,et al.  DABCO entrapped in agar-agar: A heterogeneous gelly catalyst for multi-component synthesis of 2-amino-4H-chromenes , 2013 .

[34]  A. Maleki,et al.  Potassium phthalimide-N-oxyl: a novel, efficient, and simple organocatalyst for the one-pot three-component synthesis of various 2-amino-4H-chromene derivatives in water , 2013 .

[35]  Guodong Yin,et al.  Selective Synthesis of Cyano-Functionalized 2-Aryl-4H-chromenes and 2-Amino-4H-chromene-3-carbonitriles by Catalyst-Tuned Reactions of 2-Hydroxychalcones with 2-Substituted Acetonitriles , 2013 .

[36]  H. Shaterian,et al.  Effective preparation of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene and hydroxyl naphthalene-1,4-dione derivatives under ambient and solvent-free conditions , 2013 .

[37]  A. Wu,et al.  Synthesis of functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction. , 2012, Organic & biomolecular chemistry.

[38]  M. Tajbakhsh,et al.  Well-Ordered Mesoporous Silica Nanoparticles as a Recoverable Catalyst for One-Pot Multicomponent Synthesis of 4H-Chromene Derivatives , 2012 .

[39]  A. Ramazani,et al.  One-pot synthesis of 4H-benzo[b]pyrans and dihydropyrano[c]chromenes using inorganic–organic hybrid magnetic nanocatalyst in water , 2012 .

[40]  B. Sridhar,et al.  An Efficient One‐Pot Synthesis of Substituted 1H‐Naphtho[2,1‐b]pyrans and 4H‐1‐Benzopyrans (=Chromenes) under Solvent‐Free Microwave‐Irradiation Conditions , 2012 .

[41]  H. Mehrabi,et al.  Efficient and eco-friendly synthesis of 2-amino-4H-chromene derivatives using catalytic amount of tetrabutylammonium chloride (TBAC) in water and solvent-free conditions , 2012, Journal of the Iranian Chemical Society.

[42]  A. Mobinikhaledi,et al.  Tetrabutylammonium Bromide in Water as a Green Media for the Synthesis of Pyrano[2,3-d]pyrimidinone and Tetrahydrobenzo[b]pyran Derivatives. , 2010, Acta chimica Slovenica.

[43]  Pooja Saluja,et al.  DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium , 2010 .

[44]  M. Naimi-Jamal,et al.  An efficient, multicomponent approach for solvent-free synthesis of 2-amino-4H-chromene scaffold , 2010, Molecular Diversity.

[45]  Amira M. Ahmed,et al.  Microwave Assisted One‐pot Synthesis of 2‐Amino‐4H‐chromenes and Spiropyrano[2,3‐d]pyrimidine , 2010 .

[46]  Atul Kumar,et al.  Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, three-component reactions and their anti-proliferative activity. , 2010, Journal of combinatorial chemistry.

[47]  A. Bazgir,et al.  An Efficient, Three-Component Synthesis of Spiro[benzo[g]chromene-4,3'-indoline]-3-carbonitrile and Spiro[indoline-3,5'-pyrano[2,3-d]pyrimidine]-6'-carbonitrile Derivatives , 2009 .

[48]  S. Ng,,et al.  Novel one-pot three- and pseudo-five-component reactions: synthesis of functionalized benzo[g]- and dihydropyrano[2,3-g]chromene derivatives. , 2009, Journal of combinatorial chemistry.

[49]  M. Ersoz,et al.  Immobilization of albumin on aminosilane modified superparamagnetic magnetite nanoparticles and its characterization. , 2009, Colloids and surfaces. B, Biointerfaces.

[50]  D. Fang,et al.  Basic ionic liquid as catalyst for the rapid and green synthesis of substituted 2-amino-2-chromenes in aqueous media , 2008 .

[51]  M. Kidwai,et al.  Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. , 2005, Bioorganic & medicinal chemistry letters.

[52]  T. Kakuchi,et al.  Synthesis of poly(succinimide) by bulk polycondensation of L‐aspartic acid with an acid catalyst , 2000 .

[53]  W. Stöber,et al.  Controlled growth of monodisperse silica spheres in the micron size range , 1968 .