Issue 1, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis of novel 2,8-disubstituted indolo[3,2-b]carbazoles†

Sven Van Snicka  and  Wim Dehaen*a  

* Corresponding authors

a Division of Molecular Design and Synthesis, Department of Chemistry, K. U. Leuven, Celestijnenlaan 200F, Leuven, Belgium

Abstract

A new synthetic pathway towards 2,8-difunctionalised indolo[3,2-b]carbazoles was investigated. The presented method offers a short and high yielding route towards 2,8-dibromo-5,11-dihexyl-6,12-diphenyl-indolo[3,2-b]carbazole. It is demonstrated that the latter compound is a versatile building block, enabling the synthesis of a number of previously unreported 5,11-dialkyl-6,12-diphenyl-indolo[3,2-b]carbazoles in moderate to good yields, using Suzuki and Sonogashira cross-coupling reaction. Furthermore it is shown that 2,8-dibromo-5,11-dihexyl-6,12-diphenyl-indolo[3,2-b]carbazole can be easily formylated, giving rise to the 2,8-diformyl-5,11-dihexyl-6,12-diphenyl-indolo-[3,2-b]carbazole. The latter compound was successfully subjected to condensation reactions.

Graphical abstract: Synthesis of novel 2,8-disubstituted indolo[3,2-b]carbazoles

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Article information

DOI
https://doi.org/10.1039/C1OB06298K
Article type
Paper
Submitted
29 Jul 2011
Accepted
31 Aug 2011
First published
31 Aug 2011

Org. Biomol. Chem., 2012,10, 79-82

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Synthesis of novel 2,8-disubstituted indolo[3,2-b]carbazoles

S. Van Snick and W. Dehaen, Org. Biomol. Chem., 2012, 10, 79 DOI: 10.1039/C1OB06298K

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