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Paper | Regular issue | Vol 78, No. 11, 2009, pp.2769-2776
Published online, 31st July, 2009
DOI: 10.3987/COM-09-11778
Reactions of 2-(Lithiomethyl)phenyl Isocyanides with Methyl 1-Methylindole-3-carboxylate: Flaborations of the Adducts to 5H-Benz[2,3]azepino[5,6-c]indol-12-one and 2,3’-Biindolyl Derivatives

Kazuhiro Kobayashi,* Daisuke Nakai, Shuhei Fukamachi, and Hisatoshi Konishi

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

It has been found that when 2-(lithiomethyl)phenyl isocyanides were allowed to react with methyl 1-methylindole-3-carboxylate, the corresponding 1,4- and/or 1,2-adducts were obtained. The 1,4-adducts could be transformed into 6,11-dihydro-5H-benz[2,3]azepino[5,6-b]indol-12-ones derivatives by acid hydrolysis, followed by lactamization and subsequent dehydrogenation. The transformation of the 1,2-adducts into 2,3’-biindolyls was accomplished by a sequential treatment with hydrochloric acid and aqueous sodium hydroxide.