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

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

References and notes

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20

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.