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Synthesis 2009(6): 985-999  
DOI: 10.1055/s-0028-1087983
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Partially Saturated Indeno[1,2-b]indole Derivatives via Deoxygenation of Heterocyclic α-Hydroxy-N,O-hemiaminals

Hans-Jörg Hemmerling*a,1, Guido Reissb
a Institut für Pharmazeutische und Medizinische Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany
e-Mail: H-J.Hemmerling@web.de;
b Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany
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Publication History

Received 31 July 2008
Publication Date:
02 March 2009 (online)

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Abstract

A series of 3-aminocyclohex-2-enones were reacted with indane-1,2,3-trione monohydrate (ninhydrin) yielding 4b,9b-dihydroxyindeno[1,2-b]indoles that were deoxygenated to indeno[1,2-b]indoles.

Key words

ninhydrin - deoxygenation - 3-aminocyclohex-2-enones - indeno[1,2-b]indoles - N,O-hemiaminals

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1

Present address: Dr. Hans-J. Hemmerling, Großes Feld 21, 40822 Mettmann, Germany.

19

Scattering factors, dispersion corrections and absorption coefficients were taken from International Tables for Crystallography (1992, Vol. C). Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 694526 (9B1) and CCDC 694527 (10B5). 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].

20

SHELXS-86: Sheldrick, G. M., Universität Göttingen, 1985.

21

SHELXL-97: Sheldrick, G. M., Universität Göttingen, 1997.