Synthesis of 2-formylazulene and its derivatives by oxidative cleavage of 2-styrylazulenes.

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概要

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• 2-Formylazulene and its derivatives were prepared by the oxidative cleavage of styrylazulenes with NaIO<SUB>4</SUB>−OsO<SUB>4</SUB>. 1,2-Diformyl-, 1,2,3-triformylazulenes, and 5-formylazulene derivative were also synthesized. The reaction of dimethyl 2-methylazulene-1,3-dicarboxylate with <I>p</I>-nitroso-<I>N</I>,<I>N</I>-dimethylaniline in the presence of NaOR (R=Me or Et) gave the corresponding 3-alkoxycarbonyl-2-[<I>p</I>-(dimethylamino)phenyliminomethyl]azulene-1-carboxylic acids followed by hydrolysis with hydrochloric acid to give 3-alkoxycarbonyl-2-formylazulene-1-carboxylic acids. Acetylation of 2-formylazulene-1-carboxylic acids with acetic anhydride gave five membered lactol acetates.

• 公益社団法人 日本化学会の論文

著者

• Morita Tadayoshi

  Department Of Chemistry Graduate School Of Science Tohoku University

• Takase Kahei

  Department Of Chemistry Faculty Of Science Tohoku University

• Saito Motoyasu

  Department of Chemistry, Faculty of Science, Tohoku University

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