Indole syntheses utilizing o-methylphenyl isocyanides.

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概要

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• New indole synthesis starting with <I>o</I>-methylphenyl isocyanides such as <I>o</I>-tolyl, 2,4-xylyl, and 2,6-xylyl isocyanide is described in full detail. Treatment of <I>o</I>-tolyl isocyanide with LDA in diglyme at −78 °C generated selectively <I>o</I>-(lithiomethyl)phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similary, 2,4-xylyl and 2,6-xylyl isocyanides were cyclized to 5-methylindole and 7-methylindole quantitatively. The <I>o</I>-(lithiomethyl)phenyl isocyanides reacted with electrophiles such as alkyl halides and alkylene oxides to give <I>o</I>-alkylphenyl isocyanides, which were cyclized <I>via</I> the lithiation at the orthobenzylic carbon to afford 3-substituted indoles. On the other hand, the <I>o</I>-(lithiomethyl)phenyl isocyanides generated <I>in situ</I> at −78 °C was first warmed up to room temperature and then treated with electrophiles to furnish 1-substituted indoles. The <I>o</I>-(lithiomethyl)phenyl isocyanides were acylated in a fairly good yield with <I>N</I>-acylaziridines to give <I>o</I>-(acylmethyl)phenyl isocyanides, which were readily alkylated in the presence of sodium hydride to produce <I>o</I>-(1-acylalkyl)phenyl isocyanides. On acid hydrolysis followed by neutralization, <I>o</I>-(1-acylalkyl)phenyl isocyanides were converted to 2,3-disubstituted indoles.

• 公益社団法人 日本化学会の論文

著者

• Ito Yoshihiko

  Department Of Mathematics Faculty Of Education Kumamoto University

• Saegusa Takeo

  Department Of Synthetic Chemistry Faculty Of Engineering Kyoto University

• Kobayashi Kazuhiro

  Department Of Chemical Science And Engineering Kobe University

• Kobayashi Kazuhiro

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Seko Norihiko

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

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