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.
Selenium catalyzed conversion of δ-phenyl- γ-alkenyl oximes into 2-phenylpyridines
δ-Phenyl-γ-alkenyl oximes react with an excess of ammonium persulfate and catalytic amounts of diphenyl diselenide in the presence of trifluoromethanesulfonic acid in acetonitrile to afford 2-phenylpyridines and 2-phenylpyridine N-oxides in moderate yields.
Tiecco, Marcello,Testaferri, Lorenzo,Bagnoli, Luana,Marini, Francesca,Santi, Claudio,Temperini, Andrea
p. 2679 - 2686
(2007/10/03)
THE OXIME REARRANGEMENT CYCLIZATION. ALKENYL, STYRYL AND VINYL CHLORIDE TERMINATORS IN THE SYNTHESIS OF Δ1-PYRROLINES
Functionalized γ,δ-unsaturated oximes, constructed by regiospecific alkylation of appropriate oximes, may be rearranged and cyclized to Δ1-pyrrolines in good yield.
Gawley, Robert E.,Termine, Enrico J.
p. 307 - 308
(2007/10/02)
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