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Synthesis 2010(18): 3067-3069  
DOI: 10.1055/s-0030-1258191
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© Georg Thieme Verlag Stuttgart ˙ New York

A Short, Multigram Synthesis of 1,8-Diaminocarbazole

Michał J. Chmielewski*
University of Warsaw, Faculty of Chemistry, ul. Pasteura 1, 02-093 Warszawa, Poland
Fax: +48(22)8225996; e-Mail: mchmielewski@chem.uw.edu.pl;
Further Information

Publication History

Received 21 June 2010
Publication Date:
04 August 2010 (online)

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Abstract

A one-pot, multigram, and chromatography-free procedure has been developed for the preparation of 1,8-diamino-9H-carbazole, a versatile synthon for the synthesis of anion receptors and conducting polymers. The synthesis consists of a one-pot, palladium-catalyzed reduction of nitro groups and hydrodechlorination of 3,6-dichloro-1,8-dinitrocarbazole, which in turn can be easily produced on a large scale from inexpensive carbazole.

Key words

heterocycles - amines - palladium catalysis - dechlorination - anion receptors

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CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171.NET) (compiled Nov 11 2005,15:50:43). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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Sheldrick, G. M. SHELXL93, Program for the Refinement of Crystal Structures, University of Göttingen, Germany.

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Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 770950. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].