Synthesis of indole derivatives by Cu2O-catalyzed cyclization of o-(.ALPHA.-cyanoalkyl)phenyl isocyanides and o-[.ALPHA.-(methoxycarbonyl)alkyl]phenyl isocyanides.

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概要

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• <I>o</I>-(Cyanomethyl)phenyl isocyanide and <I>o</I>-(methoxycarbonylmethyl)phenyl isocyanide were heated with a catalytic amount of Cu<SUB>2</SUB>O in benzene to give 3-cyanoindole and 3-(methoxycarbonyl)indole in 86 and 92% yields, respectively. Lithiations of <I>o</I>-(cyanomethyl)phenyl isocyanide and <I>o</I>-(methoxycarbonylmethyl)phenyl isocyanide with butyllithium at −78 °C followed by the reaction with alkyl halides such as methyl iodide, allyl bromide, butyl bromide, benzyl bromide and methyl α-bromoacetate afforded the corresponding <I>o</I>-(α-cyanoalkyl)phenyl isocyanides and <I>o</I>-[α-(methoxycarbonyl)alkyl]phenyl isocyanides. <I>o</I>-(α-Cyanoalkyl)phenyl isocyanides and <I>o</I>-[α-(methoxycarbonyl)alkyl]phenyl isocyanides thus obtained were also cyclized by Cu<SUB>2</SUB>O catalyst producing 3-alkyl-3-cyano-3<I>H</I>-indoles and 3-alkyl-3-(methoxycarbonyl)-3<I>H</I>-indoles, respectively, in moderate yields.

• 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

• SAEGUSA Takeo

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Sugaya Toru

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Inubushi Yoshinori

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

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