Formation and reaction of oxazoles. Synthesis of N-substituted 2-(aminomethyl)oxazoles.
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概要
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The BF<SUB>3</SUB>-catalyzed reaction of substituted α-diazoacetophenones with chloroacetonitrile gave 5-aryl-2-chloromethyloxazoles (<B>3</B>) in high yields. Methyl <I>p</I>-nitrophenyldiazoacetate also yielded 2-(chloromethyl)-5-methoxy-4-(<I>p</I>-nitrophenyl)oxazole. The nucleophilic substitution of <B>3</B> with primary, secondary, and tertiary amines afforded the corresponding secondary amines, tertiary amines, and quaternary ammonium salts bearing a 2-oxazolylmethyl group.
- 公益社団法人 日本化学会の論文
著者
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Ibata Toshikazu
Institute Of Chemistry College Of General Education Osaka University
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Isogami Yasushi
Institute of Chemistry, College of General Education, Osaka University
関連論文
- Nucleophilic Substitution Reaction of Aromatic Chlorides with Cyclic Tertiary Amines under High Pressure
- Formation and Reaction of Azomethine Ylide by the Reaction of Cu(acac)2-ketocarbenoids with 1,1-Diphenylmethanimine
- Formation and Reaction of Acyl Substituted Nitrile Ylide through the Rh_2(OAc)_4-Catalyzed Reaction of α-Diazocarbonyl Compounds with Benzonitrile
- Molecular structure of the exo-Diels-Alder-adduct of 5-methoxy-2-methyl-4-(p-nitrophenyl)oxazole with N-methylmaleimide.
- Synthesis and molecular structure of the 2:1-cycloadduct of 1-methoxy-2-benzopyrylium-4-olate with acenaphthylene.
- The BF3 catalyzed decomposition of diazo compounds in the presence of carbonyl compounds.
- The reaction of diazo ketones in the presence of metal chelates. VIII. The stereochemistry of the 1,3-dipolar cycloaddition of 1-methoxy-2-benzopyrylium-4-olates to ethylenic dipolarophiles.
- Formation and reaction of oxazoles. Synthesis of N-substituted 2-(aminomethyl)oxazoles.
- Aromatic nucleophilic substitution of halobenzenes with amines under high pressure.
- Reaction of diazo ketones in the presence of metal chelates. VII. 1,3-Dipolar cycloaddition of 1-methoxybenzo[c]pyrylium-4-olate with acetylenic dipolarophiles.
- The acid catalyzed decomposition of diazo compounds. I. Synthesis of oxazoles in the BF3 catalyzed reaction of diazo carbonyl compounds with nitriles.
- Formation of 1,3-oxathiole-2-thione and 1,2,4-trithiolane derivatives by the catalytic reaction of .ALPHA.-diazocarbonyl compounds with carbon disulfide.
- Formation and molecular structure of the 2:1-adducts of 1-alkoxy-2-benzopyrylium-4-olates with carbon disulfide.
- The Diels-Alder reactions of 2-alkyl-5-methoxy-4-(p-nitrophenyl)oxazoles with ethylenic, acetylenic, and azo-type dienophiles.
- The Acid-catalyzed Decomposition of α-Diazo β-Hydroxy Ketones
- Formation and reaction of carbonyl ylides. 1,3-Dipolar cycloaddition of 2-benzopyrylium-4-olates with carbonyl compounds.
- The high pressure Diels-Alder reactions of 5-methoxy-2-methyl-4-(p-nitrophenyl)oxazole with ethylenic dienophiles.
- The acid-catalyzed decomposition of diazo carbonyl compounds. II. Synthesis of 2- or 5-heteroatom-substituted oxazoles.