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Synthesis 2008(20): 3273-3278  
DOI: 10.1055/s-0028-1083152
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Versatile One-Pot Synthesis of β-Carbolines by Reaction of Pyranoindolones with Phenyl- and Benzoylhydrazine

Despina Livadiotou, Dimitra Hatzimimikou, Constantinos Neochoritis, Michael A. Terzidis, Constantinos A. Tsoleridis*, Julia Stephanidou-Stephanatou*
Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, 54124 Thessaloniki, Macedonia, Greece
Fax: +30(2310)997679; e-Mail: tsolerid@chem.auth.gr; e-Mail: ioulia@chem.auth.gr;
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Publication History

Received 13 June 2008
Publication Date:
25 September 2008 (online)

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Abstract

The synthesis of a number of 2-anilino- and 2-(benzoyl­amino)-β-carbolin-3-ones in good yields by a one-step sequence from the reaction of pyranoindolones with phenylhydrazine or benzoylhydrazine is described; the observed good regioselectivity of the reaction is discussed. Full assignment of all ¹H and ¹³C NMR chemical shifts has been unambiguously achieved.

Key words

benzoylhydrazine - p-benzylic coupling - bisnucleophiles - one-pot reaction - phenylhydrazine - pyranoindoles