Synthesis of Quinolines and 2H-Dihydropyrroles by Nucleophilic Substitution at the Nitrogen Atom of Oxime Derivatives

Abstract

Isomerization of oxime derivatives was researched in detail to find out the methods for the syn-anti isomerization of O-substituted oximes. Based on these findings were developed simple methods for the preparation of aza-heterocycles from both stereo­isomers of oximes. Quinolines were synthesized from β-aryl ketone oximes by treatment with trifluoroacetic anhydride and 4-chloranil. γ,δ-Unsaturated O-methoxyacetyloximes were transformed to 2H-dihydropyrroles by reaction with methoxy-acetic acid.

Key words

nucleophilic substitution - oxime derivatives - quinolines - tetrahydroquinolines - 2H-dihydropyrroles

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5

In this manuscript syn-isomers mean the oximes having hydroxy or acyloxy and a nucleophilic moiety in the same side of oxime carbon-nitrogen double bond and anti-isomers mean the opposite.

19

The spectral data were in good agreement with those of the authentic sample (commercially available from Tokyo Chemical Industry).

21

The spectral data were in good agreement with those of the authentic sample.