Intramolecular Aminolysis of 2′-Aminochalcone Epoxides Using InBr₃ or BiCl₃ as Efficient Catalysts

REFERENCES

• Shintani , R. ; Yamagami , T. ; Kimura , T. ; Hayashi , T. Asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones by rhodium-catalyzed 1,4-addition of arylzinc reagents in the presence of chlorotrimethylsilane . Org. Lett. 2005 , 7 , 5317 – 5319 .
   PubMed Web of Science ®Google Scholar
• Beifuss , U. ; Feder , G. ; Bes , G. ; Uson , I. The first stereoselective bifunctionalization of 4-quinolones with organometallics and n-halosuccinimides to 2,3-trans-disubstituted tetrahydroquinolones: Expected and unexpected results . Synlett 1998 , 649 – 651 .
   Web of Science ®Google Scholar
• Li , L. ; Wang , H. K. ; Kuo , S. C. ; Wu , T. S. ; Lednicer , D. ; Lin , C. ; Hamel , E. ; Lee , K. H. Antitumor agents 155: Synthesis and biological evaluation of 3’,6,7-substituted 2-phenyl-4-quinolones as antimicrotubule agents . J. Med. Chem. 1994 , 37 , 3400 – 3407
   PubMed Web of Science ®Google Scholar
• Xia , Y. ; Yang , Z.-Y. ; Xia , P. ; Bastow , K. F. ; Nakanishi , Y. , Lee , K.-H. (IUCr) (E)-3-(2,6-Dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-δ1-one . Bioorg. Med. Chem. Lett. 2000 , 10 , 699 – 701
   PubMed Web of Science ®Google Scholar
• Li , L. ; Wang , H. K. ; Kuo , S. C. ; Wu , T. S. ; Lednicer , D. ; Lin , C. ; Hamel , E. ; Lee , K. H. 2′,3′,4′,5′,5,6,7-Substituted 2-phenyl-4-quinolones and related compounds: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization . J. Med. Chem. 1994 , 37 , 1126 – 1135
   PubMed Web of Science ®Google Scholar
• Xia , Y. ; Yang , Z. Y. ; Xia , P. ; Bastow , K. ; Tachibana , Y. ; Kuo , S. C. ; Hamel , E. ; Hack , T. ; Lee , K. H. Synthesis and biological evaluation of 6,7,2′,3′,4′-substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents . J. Med. Chem. 1998 , 41 , 1155 – 1162 .
   PubMed Web of Science ®Google Scholar
• Gao , F. ; Johnson , K. F. ; Schlenoff , J. B. Ring closing and photooxidation in nitrogen analogues of 3-hydroxyflavone . J. Chem. Soc. Perkin Trans. 2 1996 , 269 – 273 .
   Google Scholar
• Cummins , B. ; Donnelly , D. M. X. ; Eades , J. F. ; Fletcher , H. ; O'Cinneide , F. ; Philbin , E. M. ; Swirski , J. ; Wheeler , T. S. ; Wilson , R. K. Oxidation of chalcones (AFO reaction) . Tetrahedron 1963 , 19 , 499 – 512 .
   Web of Science ®Google Scholar
• Oyamada , T. A new general method for the synthesis of the derivatives of flavonol . Bull. Chem. Soc. Jpn. 1935 , 10 , 182 – 186
   Google Scholar
• Dean , F. M. ; Podimuang , V. The course of the Algar–Flynn–Oyamada (A.F.O.) reaction . J. Chem. Soc. 1965 , 3978 – 3987 .
   Web of Science ®Google Scholar
• Geissman , T. A. ; Fukushima , D. K. Flavonones and related compounds, V: The oxidation of 2′-hydroxychalcones with alkaline hydrogen peroxide . J. Am. Chem. Soc. 1948 , 70 , 1686 – 1689
   PubMed Web of Science ®Google Scholar
• Donnelly , J. A. ; Fox , M. J. ; Sharma , T. C. α-Halogenoketones, 12: Extension of the Rasoda synthesis of dihydroflavonols . Tetrahedron 1979 , 35 , 1987 – 1991
   Web of Science ®Google Scholar
• Marathey , M. G. Synthesis of dihydroflavonols and flavonols . J. Org. Chem. 1955 , 20 , 563 – 571 .
   Web of Science ®Google Scholar
• Baumstark , A. L. ; Harden , D. B. Epoxidation of α -, β-unsaturated carbonyl compounds by dimethyldioxirane . J. Org. Chem. 1993 , 58 , 7615 – 7618 .
   Web of Science ®Google Scholar
• Chawla , H. M. ; Sharma , S. K. Regioselective synthesis of 2-arylidene coumaran-3-ones by dye-sensitized photooxygenation of 2-hydroxyphenyl-styrylketones in the presence of sodium dodecyl sulphate . Tetrahedron 1990 , 46 , 1611 – 1624 .
   Web of Science ®Google Scholar
• Litkei , G. ; Tokes , A. L. Oxidation of the 2′-NHR analogues of 2′-or-chalcones: Conversion of 2′-NHR-chalcone epoxides. Synth. Commun. 1991, 21, 1597–1609.
   Web of Science ®Google Scholar
• Tokes , A. L. ; Szilagyi , L. Resolution of (±)-2,3-dihydro-2-phenyl-4(1 h)-quinolone . Synth. Commun. 1987 , 17 , 1235 – 1245 .
   Web of Science ®Google Scholar
• Ahmed , N. ; van Lier , J. E. Alumina-supported-CeCl3 · 7H2O–NaI: An efficient catalyst for the cyclization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions . Tetrahedron Lett. 2007 , 48 , 13 – 15 .
   Web of Science ®Google Scholar
• Ahmed , N. ; van Lier , J. E. Molecular iodine in isopropenyl acetate (IPA): A highly efficient catalyst for the acetylation of alcohols, amines, and phenols under solvent-free conditions . Tetrahedron Lett. 2006 , 47 , 5345 – 5349 .
   Web of Science ®Google Scholar
• Ahmed , N. ; van Lier , J. E. Silica-gel-supported TaBr5: New catalyst for the facile and rapid cyclization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions . Tetrahedron Lett. 2006 , 47 , 2725 – 2729 .
   Web of Science ®Google Scholar
• Ahmed , N. ; Ali , H. ; van Lier , J. E. Silica-gel-supported InBr3 and InCl3: New catalysts for the facile and rapid oxidation of 2′-hydroxychalcones and flavanones to their corresponding flavones under solvent-free conditions . Tetrahedron Lett. 2005 , 46 , 253 – 256 .
   Web of Science ®Google Scholar
• Ahmed , N. ; Ali , H. ; van Lier , J. E. The reaction of porphyrins with α,β-acetylenic ketones/ester (MBH) promoted by MgI2 and subsequent Sonogashira coupling reactions . J. Porphyrins Phthalocyanines 2006 , 10 , 1172 – 1178 .
   Web of Science ®Google Scholar
• Ahmed , N. and Ansari , W. H. An improved procedure for the isomerisation of 2’-hydroxysubstituted chalcone to flavoanones using silica-supported BiCl3 under dry conditions . J. Chem. Res. Synop. 2003 , 572 – 573 .
   Web of Science ®Google Scholar
• Kiasat , A. R. ; Badri , R. ; Zargar , B. ; Sayyahi , S. Poly(ethylene glycol) grafted onto dowex resin: An efficient, recyclable, and mild polymer-supported phase-transfer catalyst for the regioselective azidolysis of epoxides in water . J. Org. Chem. 2008 , 73 , 8382 – 8385 .
   PubMed Web of Science ®Google Scholar
• Betti , C. ; Landini , D. ; Maia , A. Metal ion electrophilic catalysis in ring-opening reactions of 1,2-epoxides by metal halides in ILs . Synlett. 2006 , 1335 – 1338 .
   Web of Science ®Google Scholar
• McCluskey , A. ; Leitch , S. K. ; Garner , J. ; Caden , C. E. ; Stewart , S. G. BiCl3-mediated opening of epoxides, a facile route to chlorohydrins or amino alcohols: One reagent, two paths . Tetrahedron Lett. 2005 , 46 , 8229 – 8232 .
   Web of Science ®Google Scholar
• Singh , M. C. ; Peddinti , R. K. Antimony(III) chloride–catalyzed ring opening of epoxides with anilines . Tetrahedron Lett. 2007 , 48 , 7354 – 7357 .
   Web of Science ®Google Scholar
• Rodriguez , J. R. ; Navarro , A. Opening of epoxides with aromatic amines promoted by indium tribromide: A mild and efficient method for the synthesis of β-amino alcohols . Tetrahedron Lett. 2004 , 45 , 7495 – 7498 .
   Web of Science ®Google Scholar
• Kalow , J. A. ; Doyle , A. G. Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system . J. Am. Chem. Soc. 2010 , 132 , 3268 – 3269 .
   PubMed Web of Science ®Google Scholar
• Donnelly , J. A. ; Farrell , D. F Chalcone derivatives as precursors of 1,2,3,4- tetrahydro-4-quinolones . Tetrahedron 1990 , 46 , 885 – 894
   Web of Science ®Google Scholar