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Synthesis 2008(20): 3273-3278
DOI: 10.1055/s-0028-1083152
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
Further Information
Received
13 June 2008
Publication Date:
25 September 2008 (online)
Publication History
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
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References and notes
The multiplicities and chemical shifts of the aromatic protons and of some second-order spectra of R² substituent have been confirmed after simulation with program SpinWorks, version 2.5, available from ftp://davinci.chem.umanitoba.ca.