- Synthesis of Quinolines and 2H-Dihydropyrroles by Nucleophilic Substitution at the Nitrogen Atom of Oxime Derivatives
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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.
- Kitamura, Mitsuru,Yoshida, Masayuki,Kikuchi, Takashi,Narasaka, Koichi
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p. 2415 - 2426
(2007/10/03)
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- SN2 substitution on sp2 nitrogen of protonated oxime
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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.
- Mori, Seiji,Uchiyama, Katsuya,Hayashi, Yujiro,Narasaka, Koichi,Nakamura, Eiichi
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p. 111 - 112
(2007/10/03)
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- Transformation of oximes of phenetyl ketone derivatives to quinolines and azaspirotrienones catalyzed by tetrabutylammonium perrhenate and trifluoromethanesulfonic acid
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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.
- Kusama,Yamashita,Uchiyama,Narasaka
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p. 965 - 975
(2007/10/03)
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- Synthesis of Quinolines via Intramolecular Cyclization of Benzylacetone Oxime Derivatives Catalyzed with Tetrabutylammonium Perrhenate(VII) and Trifluoromethanesulfonic Acid
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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.
- Kusama, Hiroyuki,Yamashita, Yuko,Narasaka, Koichi
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- Synthesis of Azaspirodienones via Intramolecular Cyclization of p-Hydroxybenzylacetone Oximes and Their Transformation into Quinolines
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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.
- Kusama, Hiroyuki,Uchiyama, Katsuya,Yamashita, Yuko,Narasaka, Koichi
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p. 715 - 716
(2007/10/03)
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