Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines?
Organic & Biomolecular Chemistry Pub Date: 2014-06-26 DOI: 10.1039/C4OB00841C
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](http://scimg.chem960.com/usr/1/C4OB00841C.jpg)
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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