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

doi:10.1055/s-0028-1083152

PAPER

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;

Abstract

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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

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References

References and notes

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The multiplicities and chemical shifts of the aromatic protons and of some second-order spectra of R^² substituent have been confirmed after simulation with program SpinWorks, version 2.5, available from ftp://davinci.chem.umanitoba.ca.