Heterofulvalenes. II. Synthesis and reaction of 2,3:7,8-dibenzo-1,4-dithia-6-azafulvalene.

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概要

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• Reaction of 2-isopentyloxy-1,3-benzodithiole with indole in acetic acid gave a 93% yield of 3-(1,3-benzodithiol-2-yl)indole (<B>4a</B>) which was converted to 2-(3-indolyl)-1,3-benzodithiolylium tetrafluoroborate (<B>5a</B>) in a 77% yield by treatment with trityl tetrafluoroborate. <B>5a</B> was also prepared by reaction of indole with 2 molar amounts of 1,3-benzodithiolylium tetrafluoroborate. Treatment of <B>5a</B> with triethylamine afforded the title compound <B>6a</B> in 93% yield. <B>6a</B> was protonated, methylated, and benzoylated at its 6-position by tetrafluoroboric acid, methyl iodide, and benzoyl chloride, respectively. Reaction of <B>6a</B> with dimethyl acetylenedicarboxylate gave a 1,6-dipolar intermediate which was trapped as an adduct with ethanol. <B>6a</B> was smoothly reduced by sodium borohydride to give its 5,6-dihydro derivative.

• 公益社団法人 日本化学会の論文

著者

• Nakayama Juzo

  Department Of Chemistry Faculty Of Science Saitama University

• Hoshino Masamatsu

  Department of Chemistry, Faculty of Science and Engineering, Saitama University

• Imura Mimiko

  Department of Chemistry, Faculty of Science, Saitama University

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