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Paper | Regular issue | Vol 36, No. 12, 1993, pp.2783-2804
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6514
A Synthesis Method of Indole-3-methanamine and/or Gramine from Indole-3-carboxaldehyde, and Its Application for the Synthesis of Brassinin, Its 4-Substituted Analogs, and 1,3,4,5-Tetrahydropyrrolo[4,3,2-de]quinoline

Fumio Yamada, Kensuke Kobayashi, Aya Shimizu, Naokatsu Aoki, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


Simple conversion method of indole-3-carboxaldehyde into gramine and/or indole-3-methanamine was developed. The present method realized short step syntheses of brassinin, 4-iodo-, methoxy-, 4-methoxy-, and 4-nitrobrassinin, 4-methoxyindole-3-acetonitrile, and 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline.