title: L-cysteine functionalized magnetic nanoparticles (LCMNP): a novel magnetically separable organocatalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitriles in water.
abstract: In this study, L-cysteine was chemically grafted to magnetic nanoparticles in order to prepare a reusable magnetic material incorporating an amino acid moiety. For this purpose, silica-coated magnetic nanoparticles (Fe3O4@SiO2) were reacted with trimethoxy(vinyl)silane to produce vinyl-functionalized magnetic nanoparticles (VMNP). Reaction of a VMNP substrate with L-cysteine in the presence of azobisisobutyronitrile (AIBN) resulted in the production of L-cysteine-functionalized magnetic nanoparticles (LCMNP). The LCMNP material was characterized using different microscopy and spectroscopy techniques such as FT-IR, XRD, TEM, SEM, EDX, VSM, and elemental analysis. Also, LCMNP was analyzed by thermogravimetric analysis (TGA) in order to determine its thermal behavior. The applicability of the LCMNP material was evaluated in a three-component coupling reaction between a nucleophile, salicylaldehyde and malononitrile as the catalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives. The catalyst system showed high catalytic activity in this process and target products were obtained in high isolated yields in water as a green solvent. The LCMNP catalyst was reusable in this reaction at least 7 times with no significant decrease in its catalytic activity.
authors.affiliation: Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran. khalafi@chem.susc.ac.ir Panahi@shirazu.ac.ir.
authors.forename: Ali
authors.initials: A
authors.lastname: Khalafi-Nezhad
authors.forename: Maryam
authors.initials: M
authors.lastname: Nourisefat
authors.forename: Farhad
authors.initials: F
authors.lastname: Panahi
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003545:Cysteine / Q000737:chemistry*; D060328:Magnetic Phenomena; D058185:Magnetite Nanoparticles / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010316:Particle Size; D012821:Silanes / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry; D013499:Surface Properties; D014867:Water / Q000737:chemistry*
chemical_list: C572731:2-amino-4H-chromene-3-carbonitrile; D001578:Benzopyrans; D058185:Magnetite Nanoparticles; D009570:Nitriles; D012821:Silanes; D014867:Water; D012822:Silicon Dioxide; C004526:azobis(isobutyronitrile); D003545:Cysteine