A Surprising Formation of Novel Bridged Bis-Benzimidazoles by Oxidation of Diaminoquinoxalines

被引:5
作者
Pressler, Jens [1 ]
Beckert, Rainer [1 ]
Rau, Sven [4 ]
Menzel, Roberto [1 ]
Birckner, Eckhard [2 ]
Guenther, Wolfgang [1 ]
Goerls, Helmar [3 ]
机构
[1] Univ Jena, Inst Organ & Makromol Chem, D-07743 Jena, Germany
[2] Univ Jena, Inst Phys Chem, D-07743 Jena, Germany
[3] Univ Jena, Inst Anorgan & Analyt Chem, D-07743 Jena, Germany
[4] Univ Ulm, Inst Anorgan Chem 1, D-89081 Ulm, Germany
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2012年 / 67卷 / 04期
关键词
Bis-Benzimidazoles; ortho-Annulation; Quinoxalines; Fluorophores; METAL-COMPLEXES; MINOR-GROOVE; DERIVATIVES; FLUORESCENT;
D O I
10.5560/ZNB.2012.67b0367
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A synthesis of novel hexacyclic bis-benzimidazoles 6 starting from 2,3-diarylamino-quinoxalines via an oxidative cyclization cascade is described. These very stable and high-melting derivatives are featured by their strong fluorescence in the blue region of the visible spectrum. The cyclization reaction between 2,3-dichloroquinoxaline and 1,2-phenylenediamine did not lead to derivatives of type 6. In this case, only fluoflavine 7 was isolated quantitatively.
引用
收藏
页码:367 / 372
页数:6
相关论文
共 35 条
  • [1] Annulated derivatives of 2,2'-biimidazole, 2-(2'-imidazolyl)benzimidazole, and 2,2'-bibenzimidazole
    Ames, JR
    Houghtaling, MA
    Terrian, DL
    Mitchell, TP
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (01): : 28 - 36
  • [2] [Anonymous], ANGEW CHEM
  • [3] Beckert R, 1997, PHARMAZIE, V52, P638
  • [4] A New Synthesis of Push-Pull Pyrroles, Their Oxidation to Stable 3H-Pyrroles and an Unexpected Anellation Reaction
    Buehrdel, Gunther
    Beckert, Rainer
    Herzigova, Petra
    Petrlikova, Eva
    Schuch, Dirk
    Birckner, Eckhard
    Goerls, Helmar
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (20) : 3404 - 3412
  • [5] Structurally Sophisticated Octahedral Metal Complexes as Highly Selective Protein Kinase Inhibitors
    Feng, Li
    Geisselbrecht, Yann
    Blanck, Sebastian
    Wilbuer, Alexander
    Atilla-Gokcumen, G. Ekin
    Filippakopoulos, Panagis
    Kraeling, Katja
    Celik, Mehmet Ali
    Harms, Klaus
    Maksimoska, Jasna
    Marmorstein, Ronen
    Frenking, Gernot
    Knapp, Stefan
    Essen, Lars-Oliver
    Meggers, Eric
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) : 5976 - 5986
  • [6] Synthesis, X-ray crystal structures, and computational studies of 1,1′-bridged 4,4′-diaryl-2,2′-bibenzimidazoles: building blocks for supramolecular structures
    Frantz, Derik K.
    Sullivan, Ashley A.
    Yasui, Yoshizumi
    Linden, Anthony
    Baldridge, Kim K.
    Siegel, Jay S.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (11) : 2347 - 2352
  • [7] Ganapaty S, 2008, ASIAN J CHEM, V20, P3353
  • [8] Ganapaty S, 2007, INDIAN J HETEROCY CH, V16, P283
  • [9] Molecular design of a proton-induced molecular switch based on rod-shaped Ru dinuclear complexes with bis-tridentate 2,6-bis(benzimidazol-2-yl) pyridine derivatives
    Haga, M
    Takasugi, T
    Tomie, A
    Ishizuya, M
    Yamada, T
    Hossain, MD
    Inoue, M
    [J]. DALTON TRANSACTIONS, 2003, (10) : 2069 - 2079
  • [10] Hahn F.E., 2000, ANGEW CHEM, V112, P551