Synthesis and characterization of bromine source immobilized on diethylenetriamine‐functionalized magnetic nanoparticles: A novel, versatile and highly efficient reusable catalyst for organic synthesis

Bromine source immobilized on magnetic nanoparticles functionalized with diethylenetriamine was successfully synthesized and characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, vibrating sample magnetometry, thermogravimetric analysis and X-ray diffraction. The catalytic activity in the synthesis of 2,3-dihydroquinazoline-4(1H)-one and polyhydroquinoline derivatives and in Knoevenagel condensation was studied. The bromine catalyst can be magnetically recovered and reused several times without significant loss of its catalytic activity. All products were obtained in high to excellent yields.

[1]  A. Ghorbani‐Choghamarani,et al.  S–S Bond Formation: Nanocatalysts in the Oxidative Coupling of Thiols , 2017 .

[2]  A. Ghorbani‐Choghamarani,et al.  Cu–S‐(propyl)‐2‐aminobenzothioate on magnetic nanoparticles: highly efficient and reusable catalyst for synthesis of polyhydroquinoline derivatives and oxidation of sulfides , 2016 .

[3]  A. Ghorbani‐Choghamarani,et al.  Sulfides Synthesis: Nanocatalysts in C–S Cross-Coupling Reactions , 2016 .

[4]  A. Ghorbani‐Choghamarani,et al.  The first report on the eco-friendly synthesis of 5-substituted 1H-tetrazoles in PEG catalyzed by Cu(II) immobilized on Fe3O4@SiO2@L-arginine as a novel, recyclable and non-corrosive catalyst , 2016 .

[5]  M. Hajjami,et al.  Incredible Role of Glycerol in Multicomponent Synthesis of 2,3-Dihydroquinazoline-4(1H)-ones and 1-Amidoalkyl-2-naphthols , 2015 .

[6]  Shuang Li,et al.  Knoevenagel condensation of aromatic aldehydes with active methylene compounds catalyzed by lipoprotein lipase , 2015 .

[7]  A. Ghorbani‐Choghamarani,et al.  Synthesis, characterization, and application of Fe3O4-SA-PPCA as a novel nanomagnetic reusable catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and polyhydroquinolines , 2015 .

[8]  A. Ghorbani‐Choghamarani,et al.  Synthesis of copper (II)-supported magnetic nanoparticle and study of its catalytic activity for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones , 2014 .

[9]  C. Girija,et al.  Simple and practical procedure for Knoevenagel condensation under solvent-free conditions , 2014 .

[10]  J. Safari,et al.  Efficient synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in the presence of nanocomposites under microwave irradiation , 2014 .

[11]  D. Astruc,et al.  Fast-growing field of magnetically recyclable nanocatalysts. , 2014, Chemical reviews.

[12]  T. Sarkar,et al.  Visible Light Induced Knoevenagel Condensation Catalyzed by Starfruit Juice of Averrhoa carambola , 2014 .

[13]  A. T. Khan,et al.  Synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones involving one-pot three-component tandem Knoevenagel–Michael reaction catalyzed by n-tetrabutylammonium tribromide (TBATB) , 2014 .

[14]  A. Ghorbani‐Choghamarani,et al.  DABCO tribromide immobilized on magnetic nanoparticle as a recyclable catalyst for the chemoselective oxidation of sulfide using H2O2 under metal- and solvent-free conditions , 2014 .

[15]  J. Safari,et al.  Environmentally friendly synthesis of 2-aryl-2,3- dihydroquinazolin-4(1H)-ones by novel Co-CNTs as recoverable catalysts , 2013 .

[16]  Pravin V. Shinde,et al.  A facile and rapid access towards the synthesis of 2,3-dihydroquinazolin-4(1H)-ones , 2013 .

[17]  T. Helleday,et al.  A new concise synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives , 2013 .

[18]  A. Davoodnia,et al.  Tetrabutylammonium hexatungstate [TBA]2[W6O19]: Novel and reusable heterogeneous catalyst for rapid solvent-free synthesis of polyhydroquinoline via unsymmetrical Hantzsch reaction , 2013 .

[19]  N. Masoud,et al.  Silica-supported DABCO-tribromide: A recoverable reagent for oxidation of alcohols to the corresponding carbonyl compounds , 2013 .

[20]  Mohammad Norouzi,et al.  Protic pyridinium ionic liquid as a green and highly efficient catalyst for the synthesis of polyhydroquinoline derivatives via Hantzsch condensation in water , 2013 .

[21]  H. Sharghi,et al.  Tin oxide nanoparticles (NP-SnO2): preparation, characterization and their catalytic application in the Knoevenagel condensation , 2013, Journal of the Iranian Chemical Society.

[22]  Jia Xiao,et al.  Efficient and reusable amine-functionalized polyacrylonitrile fiber catalysts for Knoevenagel condensation in water , 2012 .

[23]  A. Ghorbani‐Choghamarani,et al.  Synthesis of 2,3-dihydroquinazolin-4(1H)-ones via one-pot three-component reaction catalyzed by l-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate (supported on silica gel) as novel and recoverable catalyst , 2012, Journal of the Iranian Chemical Society.

[24]  A. Rostami,et al.  Sulfamic acid as a reusable and green catalyst for efficient and simple synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones in water or methanol , 2011 .

[25]  A. Ghorbani‐Choghamarani,et al.  Polyvinylpolypyrrolidoniume tribromide as new and metal-free catalyst for the formylation and trimethylsilylation of hydroxyl group , 2011 .

[26]  M. Saha,et al.  Palladium(0) nanoparticles: an efficient catalyst for the one-pot synthesis of polyhydroquinolines , 2011 .

[27]  D. S. Gaikwad,et al.  One-pot multi-component synthesis of polyhydroquinolines at ambient temperature , 2011 .

[28]  Luigi Vaccaro,et al.  Ring-Opening of Epoxides in Water , 2011 .

[29]  K. Niknam,et al.  Silica-bonded N-propylsulfamic acid as a recyclable catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones , 2011 .

[30]  C. Cai,et al.  Iodine: Selectively Promote the Synthesis of Mono Substituted Quinazolin-4(3H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones in One-Pot , 2010 .

[31]  A. T. Khan,et al.  Synthesis of highly functionalized piperidines by one-pot multicomponent reaction using tetrabutylammonium tribromide (TBATB) , 2010 .

[32]  K. Sirisha,et al.  Facile Synthesis and Antibacterial, Antitubercular, and Anticancer Activities of Novel 1,4‐Dihydropyridines , 2010, Archiv der Pharmazie.

[33]  A. Fakhari,et al.  Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst , 2010 .

[34]  A. Heydari,et al.  One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives in fluoro alcohols , 2009 .

[35]  M. Shingare,et al.  Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions , 2009 .

[36]  M. Rueping,et al.  Asymmetric Brønsted acid catalysis: catalytic enantioselective synthesis of highly biologically active dihydroquinazolinones. , 2009, Angewandte Chemie.

[37]  R. Goddard,et al.  Direct catalytic asymmetric synthesis of cyclic aminals from aldehydes. , 2008, Journal of the American Chemical Society.

[38]  A. Maleki,et al.  Click Reaction: Highly Efficient Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones , 2008 .

[39]  Atul Kumar,et al.  Efficient Synthesis of Hantzsch Esters and Polyhydroquinoline Derivatives in Aqueous Micelles , 2008 .

[40]  Sun Gi Kim,et al.  Facile synthesis of benzo-fused 2,8-dioxabicyclo[3.3.1]nonane derivatives via a domino Knoevenagel condensation/hetero-Diels–Alder reaction sequence , 2008 .

[41]  M. Kumari,et al.  MCM-41 catalyzed rapid and efficient one-pot synthesis of polyhydroquinolines via the Hantzsch reaction under solvent-free conditions , 2007 .

[42]  W. Su,et al.  Eco-friendly synthesis of 2,3 -dihydroquinazolin -4 (1H) -ones in ionic liquids or ionic liquid-water without additional catalyst , 2007 .

[43]  Yi Qun Li,et al.  Knoevenagel condensation catalysed by poly（vinyl chloride） supported tetraethylenepentamine （PVC-TEPA） , 2007 .

[44]  F. Bamoharram,et al.  K7[PW11CoO40]-catalyzed one-pot synthesis of polyhydroquinoline derivatives via the Hantzsch three component condensation , 2007 .

[45]  B. M. Reddy,et al.  An easy-to-use heterogeneous promoted zirconia catalyst for Knoevenagel condensation in liquid phase under solvent-free conditions , 2006 .

[46]  F. Bamoharram,et al.  On Water: An Efficient Knoevenagel Condensation using 12‐Tungstophosphoric Acid as a Reusable Green Catalyst , 2006 .

[47]  R. Gibbs,et al.  An efficient one-pot synthesis of polyhydroquinoline derivatives through the Hantzsch four component condensation , 2006 .

[48]  M. Dabiri,et al.  Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using KAl(SO4)2·12H2O as a reusable catalyst in water and ethanol , 2005 .

[49]  Ge Zemei,et al.  An Efficient and Green Procedure for the Knoevenagel Condensation Catalyzed by Urea , 2005 .

[50]  J. Kido,et al.  Synthesis and electroluminescent property of poly(p-phenylenevinylene)s bearing triarylamine pendants , 2005 .

[51]  W. Voelter,et al.  A Novel Method for the Synthesis of 4(3H)‐Quinazolinones. , 2004 .

[52]  T. Loh,et al.  Facile Ionic Liquids-Promoted One-Pot Synthesis of Polyhydroquinoline Derivatives under Solvent Free Conditions , 2004 .

[53]  K. Nagaiah,et al.  Phosphane‐Catalyzed Knoevenagel Condensation: A Facile Synthesis of α‐Cyanoacrylates and α‐Cyanoacrylonitriles , 2004 .

[54]  K. Nagaiah,et al.  An Eco‐Friendly Synthesis of Electrophilic Alkenes Catalyzed by Dimethylaminopyridine Under Solvent‐Free Conditions , 2004 .

[55]  L. Tietze,et al.  Domino reactions in the synthesis of heterocyclic natural products and analogs , 2004 .

[56]  J. Yadav,et al.  A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature , 2003 .

[57]  S. Kuo,et al.  6-Alkylamino- and 2,3-dihydro-3'-methoxy-2-phenyl-4-quinazolinones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization. , 2000, Journal of medicinal chemistry.

[58]  J. Aramini,et al.  Reactions of salicylaldehydes with alkyl cyanoacetates on the surface of solid catalysts: syntheses of 4H-chromene derivatives , 2000 .

[59]  F. Bigi,et al.  Montmorillonite KSF as an Inorganic, Water Stable, and Reusable Catalyst for the Knoevenagel Synthesis of Coumarin-3-carboxylic Acids. , 1999, The Journal of organic chemistry.

[60]  M. Lakshmi Kantam,et al.  Mn(III) salen catalyst for Knoevenagel condensation – a novel heterogeneous system , 1998 .

[61]  G. Kraus,et al.  Synthesis of a precursor to quassimarin , 1986 .

[62]  F. Freeman.  PROPERTIES AND REACTIONS OF YLIDENEMALONONITRILES , 1980 .