36145-03-6Relevant articles and documents
The regioselective homocoupling of meta-hydroxypyridines with hypervalent iodine(iii)
Yang, Ping Syun,Tsai, Mi Ting,Tsai, Meng Han,Ong, Chi Wi
, p. 849 - 852 (2015)
The C-H homocoupling of meta-hydroxypyridines with phenyliodine(III) diacetate (PIDA) was carried out in dichloromethane at room temperature in the presence of cesium carbonate. The coupling reaction is highly regioselective with respect to the hydroxy group at the pyridine ring. Comparative control experiments with meta-alkoxypyridine suggest that the meta-hydroxy group at the pyridine ring plays a key role during the homocoupling reaction.
A Simple Synthesis of Dihydroxybipyridyls
Naumann, Christoph,Langhals, Heinz
, p. 279 - 281 (1990)
Dihydroxybipyridyls (dihydroxybipyridines), laser dyes with large Stokes shifts, are prepared by a simple one-step synthesis from the corresponding 2-bromo-3-hydroxypyridines, 3-bromo-4-hydroxyisoquinoline and 2-bromo-3-hydroxyquinoline, using zinc, and nickel(0) in yields up to 45percent.
Metal-ion sensing europium(III) complexes with bidentate phosphine oxide ligands containing a 2,2′-bipyridine framework
Hasegawa, Yasuchika,Hieda, Ryo,Nakagawa, Tetsuya,Kawai, Tsuyoshi
experimental part, p. 2238 - 2248 (2010/03/30)
Novel EuIII complexes with bidentate phosphine oxide ligands containing a bipyridine framework, i.e., [3,3′-bis(diphenylphosphoryl)-2, 2′-bipyridine]tris(hexafluoroacetylacetonato)europium(III) ([Eu-(hfa) 3(BIPYPO)]) and [3,3′-bis(diphenylphosphoryl)-6,6′- dimethyl-2,2′-bipyridine]tris(hexafluoroacetylacetonato)europium(III) ([Eu(hfa)3(Me-BIPYPO)]), were synthesized for lanthanide-based sensor materials having high emission quantum yields and effective chemosensing properties. The emission quantum yields of [Eu(hfa)3(BIPYPO)] and [Eu(hfa)3(Me-BIPYPO)] were 71 and 73%, respectively. Metal-ion sensing properties of the EuIII complexes were also studied by measuring the emission spectra of EuIII complexes in the presence of ZnII or CuII ions. The metal-ion sensing and the photophysical properties of luminescent EuIII complexes with a bidentate phosphine oxide containing 2,2′-bipyridine framework are demonstrated for the first time.
New syntheses of orelline and analogues via metalation and cross-coupling reactions
Mongin, Florence,Trécourt, Fran?ois,Mongin, Olivier,Quéguiner, Guy
, p. 309 - 314 (2007/10/03)
New total syntheses of orelline and some analogues are reported. The methodology involves metalation of 3-alkoxy-2-iodopyridines to afford 3,4-dialkoxy-2-iodopyridines, on which cross-coupling reactions are performed to reach the 2,2′-bipyridine skeleton of the alkaloid.
Syntheses of Hydroxylated Bipyridines, III. - Synthesis of Unsymmetrically and Symmetrically Structured Dihydroxybipyridines
Dehmlow, Eckehard V.,Sleegers, Arthur
, p. 953 - 960 (2007/10/02)
Fifteen symmetrical and asymmetrical dimethoxybipyridines and the pertinent diols are prepared and characterized.Reductive cross coupling of halopyridines with Ni(0) may result in complex mixtures.The same is true for an alternative reaction of (trimethylstannyl)pyridines with halopyridines in the presence of Pd(0).UV, 1H-, and 13C-NMR spectra of the bipyridine derivatives are tabulated.Key Words: Bipyridinediols / Pyridines / Stannylpyridines
Notiz zur chemischen Reaktivitaet von hydroxylierten Pyridinen
Dehmlow, Eckehard V.,Schulz, Hans-Joachim
, p. 2951 - 2973 (2007/10/02)
Ueber mehrere Schritte werden Maltol in 3,4-Dimethoxy-2-methylpyridin (2b) und Kojisaeure in 3-Brom-4-hydroxy-5-methoxypyridin ueberfuehrt.Die Bromierung von 3,3'-Dihydroxy-2,2'-bipyridin (6) liefert ein Gemisch von Monobrom-, Dibrom-, Tribrom- und Tetrabromverbindungen 7a bis 7g, bei denen die 6-Bromderivate vorherrschen.Aehnliche Substitutionsmuster werden bei der Nitrierung von 6 erhalten, wobei die Verbindungen 7h - 7j erhalten werden.Ausgehend von 2-Iod-3-methoxypyridin (8) lassen sich die Substitutionsprodukte 10 bis 15 darstellen.Als besonders interessant erweist sich 3-Methoxy-2-iod-6-nitropyridin (11), das sich zu dem 3,3',6,6'-Tetrahydroxy-2,2'-bipyridin (16d) umwandeln laesst, einen Isomeren des Naturstoffs Orellin.
Fluorescent Dyes with Large Stokes Shifts - a Simple Synthesis of -3,3'-diol
Langhals, Heinz,Pust, Stefan
, p. 4674 - 4681 (2007/10/02)
-3,3'-diol (4) is obtained in one step from furoin (8) by Zincke rearrangement in 32percent yield.The fluorescence quantum yield of the dye is 50percent in chloroform - absorption and fluorescence spectra are completely separated (TZ = 1011).The large Stokes shift is caused by a proton transfer according to the Foerster mechanism.
BIPYRIDINES. PART XVII. A CONVENIENT SYNTHESIS OF SOME BIPYRIDINEDIOLS AND FURODIPYRIDINES
Kaczmarek, Lukasz
, p. 1141 - 1148 (2007/10/02)
A convenient method of synthesizing some bipyridinediols and furodipyridines based on diazotization of corresponding diamines in H2SO4 has been described.
Bipyridines. Part XVIII. On the Synthesis of -3-ol and Other Novel 2,2'-Bipyridine Derivatives from -3,3'-diamine
Kaczmarek, Lukasz
, p. 401 - 409 (2007/10/02)
-3-hydroxylamine (6) and its 3'-acetylderivative (7) were obtained by diazotization of -3,3'-diamine (3) in acetic acid, however, diazotization of copper(II) complex of 3 led to -3-amine (10).The amine 10 was transformed into -3-ol (2).The pethway of the reaction was proposed.