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Hung TQ, Hoang do H, Thang NN, et al. Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines. Org Biomol Chem. 2014;12(32):6151-66doi: 10.1039/c4ob00841c.
Hung, T. Q., Hoang, d. o. . H., Thang, N. N., Dang, T. T., Ayub, K., Villinger, A., Friedrich, A., Lochbrunner, S., Flechsig, G. U., & Langer, P. (2014). Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines. Organic & biomolecular chemistry, 12(32), 6151-66. https://doi.org/10.1039/c4ob00841c
Hung, Tran Quang, et al. "Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines." Organic & biomolecular chemistry vol. 12,32 (2014): 6151-66. doi: https://doi.org/10.1039/c4ob00841c
Hung TQ, Hoang do H, Thang NN, Dang TT, Ayub K, Villinger A, Friedrich A, Lochbrunner S, Flechsig GU, Langer P. Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines. Org Biomol Chem. 2014 Aug 28;12(32):6151-66. doi: 10.1039/c4ob00841c. Epub 2014 Jul 08. PMID: 25001519.
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Org Biomol Chem. 2014 Aug 28;12(32):6151-66. doi: 10.1039/c4ob00841c. Epub 2014 Jul 08.

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

Organic & biomolecular chemistry

Tran Quang Hung, Do Huy Hoang, Ngo Ngoc Thang, Tuan Thanh Dang, Khurshid Ayub, Alexander Villinger, Aleksej Friedrich, Stefan Lochbrunner, Gerd-Uwe Flechsig, Peter Langer

Affiliations

  1. Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany. [email protected] [email protected].

PMID: 25001519 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.

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