161644-20-8

Upstream product

• 52271-43-9 4-(4-methoxyphenyl)-2-butanone oxime 
• 58484-75-6 (E)-4-(4-hydroxyphenyl)butan-2-one oxime 
• 191484-60-3 (E)-4-(4-methoxyphenyl)butan-2-one oxime 

Relevant academic research and scientific papers

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

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.

SN2 substitution on sp2 nitrogen of protonated oxime

Theoretical studies on intramolecular nucleophilic displacement of the prolonated oxime oxygen willi an aryl ring revealed that the substitution reaction on the sp2 nitrogen atom is a low energy process. This seemingly anomalous substitution is due to the low-lying σ*-orbital of the O-protonated oxime. The theoretical conclusion received experimental support.

Transformation of oximes of phenetyl ketone derivatives to quinolines and azaspirotrienones catalyzed by tetrabutylammonium perrhenate and trifluoromethanesulfonic acid

Phenethyl ketone oximes are converted to quinolines by the treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and chloranil in refluxing 1,2-dichloroethane. Azaspirotrienones can be synthesized from p-hydroxyphenethyl or 3-(p-hydroxyphenyl)propyl ketone oximes by applying the above method. Thus prepared azaspirotrienones are converted to quinolines by acid treatment.

Synthesis of Quinolines via Intramolecular Cyclization of Benzylacetone Oxime Derivatives Catalyzed with Tetrabutylammonium Perrhenate(VII) and Trifluoromethanesulfonic Acid

Intramolecular cyclization reaction on the nitrogen atom of benzylacetone oxime derivatives, which have electron donating group(s) on the phenyl group, proceeds by treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and 4-chloranil in refluxing 1,2-dichloroethane to afford quinoline derivatives in good yield.

Synthesis of Azaspirodienones via Intramolecular Cyclization of p-Hydroxybenzylacetone Oximes and Their Transformation into Quinolines

Intramolecular cyclization reaction on the nitrogen atom of oximes of p-hydroxybenzylacetone derivatives proceeds by the treatment with tetrabutylammonium perrhenate and trifluoromethanesulfonic acid in refluxing 1,2-dichloroethane to afford azaspirodienones in good yield.The azaspirodienones are transformed into quinolines via dienone-phenol rearrangement.