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Issue 32, 2014
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Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines

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Abstract

A series of indolo[2,3-b]quinoxaline derivatives were efficiently synthesized from 2,3-dibromoquinoxaline by two pathways. A one-pot approach using Pd-catalyzed two-fold C–N coupling and C–H activation reactions gave indolo[2,3-b]quinoxaline derivatives in good yields, but with limited substrate scope. In addition, a two-step approach to indolo[2,3-b]quinoxalines was developed which is based on Pd-catalyzed Suzuki coupling reactions and subsequent annulation by Pd-catalyzed two-fold C–N coupling with aromatic and aliphatic amines. The electrochemical and photochemical properties of indolo[2,3-b]quinoxaline derivatives were investigated. These studies show that 6-(4-methoxyphenyl)-6H-indolo[2,3-b]quinoxaline showed the highest HOMO energy level and lowest band gap.

Graphical abstract: Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines

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Publication details

The article was received on 23 Apr 2014, accepted on 25 Jun 2014 and first published on 26 Jun 2014


Article type: Paper
DOI: 10.1039/C4OB00841C
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 6151-6166
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    Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines

    T. Q. Hung, D. H. Hoang, N. N. Thang, T. T. Dang, K. Ayub, A. Villinger, A. Friedrich, S. Lochbrunner, G. Flechsig and P. Langer, Org. Biomol. Chem., 2014, 12, 6151
    DOI: 10.1039/C4OB00841C

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