The reaction of 1,3,5-triazine with aromatic nitrile oxides. A new synthesis of 3-substituted 1,2,4-oxadiazoles.

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概要

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• The cycloaddition of aromatic nitrile oxides(<B>2a</B>=benzo-; <B>2b</B>=<I>p</I>-tolu-; <B>2c</B>=mesitylenecarbo-) with 1,3,5-triazine(<B>1</B>) is reported. The corresponding 3-substituted 1,2,4-oxadiazoles(<B>3a</B>,<B>b</B>,<B>c</B>) are obtained in fair yields only when BF<SUB>3</SUB> is added. It was stoichiometrically confirmed that one mol of <B>1</B> behaves so as to supply three mols of azomethine radicals. A reaction scheme initiated from a two-step cycloaddition of <B>2</B> to <B>1</B> activated by BF<SUB>3</SUB> is suggested. The mixture, <B>1</B> : <B>2c</B> : BF<SUB>3</SUB>=1 : 3 : 1, afforded a better yield of <B>3c</B>(69%) than an equimolar mixture of <B>2c</B> with ethyl formimidate or formamidine.

• 公益社団法人 日本化学会の論文

著者

• Kurabayashi Masahiro

  National Chemical Laboratory for Industry

• Grundmann Christoph

  National Chemical Laboratory for Industry

関連論文

• A Method of Synthesizing Pyrimidine Derivatives. II
• Reaction of 1,3-Oxazinium Salt with Active Methylene Compounds
• The reaction of 1,3,5-triazine with aromatic nitrile oxides. A new synthesis of 3-substituted 1,2,4-oxadiazoles.

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