Synthesis and Reactions of 4-Dimethylsulfuranylidene-2,3-dioxotetrahydrofuran Derivatives

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概要

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• The cyclic sulfonium ylides, 4-dimethylsulfuranylidene-2,3-dioxotetrahydrofuran derivatives (<B>8</B>), were synthesized in good yields by reactions of methyl and ethyl dimethylsulfuranylidenepyruvates (<B>3</B> and <B>4</B>) with carbonyl compounds. The reactions of <B>8</B> with <I>p</I>-toluenesulfonyl chloride and benzoyl chloride gave 4-methylthio-3-(<I>p</I>-toluenesulfonyloxy)- and 4-methylthio-3-benzoyloxy-2-oxo-2,5-dihydrofuran derivatives respectively in high yields. The ylides (<B>8</B>) reacted with mercaptans to afford 4-substituted products (<B>14</B>–<B>16</B>), whereas, on the reactions with thiourea, the demethylation of the dimethylsulfonium group proceeded exclusively.

• 公益社団法人 日本化学会の論文

著者

• Takei Hisashi

  Laboratory of Organic Chemistry Tokyo Institute of Technology

• YONEDA Naoto

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

• Hagio Katsuaki

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

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