The acid-catalyzed decomposition of diazo carbonyl compounds. II. Synthesis of 2- or 5-heteroatom-substituted oxazoles.

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概要

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• The BF<SUB>3</SUB>-catalyzed decomposition of <I>m</I>- and <I>p</I>-substituted α-diazoacetophenones in excess of methyl thiocyanate and ethyl thiocyanate gave the corresponding 2-methylthio-, and 2-ethylthio-5-aryloxazoles, respectively in good yields along with <I>s</I>-alkyl-<I>n</I>-aroylmethylthiocarbamates and α-ethoxyacetophenones. However, yields of 2-dimethylamino-5-aryloxazoles by the reaction of dimethylcyanamide with α-diazoacetophenones were poor. 5-Dimethylamino- or 5-alkoxy-4-aryl-2-methyloxazoles were prepared by the reaction of <I>N</I>,<I>N</I>-dimethyl-α-(<I>p</I>-nitrophenyl)diazoacetamide or alkyl aryldiazoacetates with nitriles. When ethyl phenyldiazoacetate or methyl <I>p</I>-chlorophenyldiazoacetate were used, ketazines of alkyl arylglyoxylates were obtained together with oxazoles.

• 公益社団法人 日本化学会の論文

著者

• Yamashita Tsuyoshi

  Institute Of Applied Beam Science Graduate School Of Science And Engineering Ibaraki University

• Ibata Toshikazu

  Institute Of Chemistry College Of General Education Osaka University

• Nakawa Hiroyuki

  Institute of Chemistry, College of General Education, Osaka University

• Kashiuchi Makoto

  Institute of Chemistry, College of General Education, Osaka University

• Nakano Shyuji

  Institute of Chemistry, College of General Education, Osaka University

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• 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.

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