title: Synthesis of chromeno[3,4-B]quinoline derivatives by heterogeneous [Cu(II)BHPPDAH] catalyst without being immobilized on any support under mild conditions using PEG 300 as green solvent.
abstract: The efficient synthesis of chromeno[3,4-[Formula: see text]]quinoline derivatives by condensation of O-propargylated salicylaldehyde, or corresponding compounds and primary aromatic amine derivatives using a catalytic amount of heterogeneous Cu(II)BHPPDAH complex without being immobilized on any supports (5.0 mol%) in PEG 300 as a "green" solvent is described. The remarkable features of this protocol are good to high yields in all cases, short reaction times, a cleaner reaction profile in an environmentally benign solvent (PEG 300), and the method is applicable to large-scale operation without any problem. Furthermore, the catalyst was quantitatively recovered from the reaction mixture by simple filtration and reused at least seven times with almost consistent activity.
authors: Department of Chemistry, Shiraz University, 71454 , Shiraz, Iran, shashem@chem.susc.ac.ir.
authors: Hashem
authors: H
authors: Sharghi
authors: Reza
authors: R
authors: Khalifeh
authors: Zahra
authors: Z
authors: Rashidi
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011092:Polyethylene Glycols / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents
chemical_list: D011804:Quinolines; D012997:Solvents; D011092:Polyethylene Glycols; D003300:Copper; C037219:quinoline
references: J Org Chem. 1998 Feb 6;63(3):864-866
references: 11672084
references: Bioorg Med Chem Lett. 2007 Jul 15;17(14):4053-6
references: 17482813
references: J Chromatogr A. 2010 Apr 16;1217(16):2495-511
references: 20022016
references: Org Lett. 2000 Dec 14;2(25):4063-5
references: 11112644
references: J Med Chem. 2003 Sep 11;46(19):4104-12
references: 12954062
references: J Chromatogr A. 2010 Apr 16;1217(16):2268-86
references: 19766228
references: Bioorg Med Chem. 2009 May 15;17(10):3720-7
references: 19398344
references: J Environ Biol. 2008 Jul;29(4):479-84
references: 19195385
references: J Nat Prod. 2009 Nov;72(11):2053-7
references: 19835393
references: Chem Rev. 2000 Mar 8;100(3):1025-74
references: 11749257
references: J Org Chem. 2003 Apr 18;68(8):3238-40
references: 12688796
references: J Med Chem. 2001 Aug 30;44(18):2879-85
references: 11520196