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Paper | Regular issue | Vol 83, No. 4, 2011, pp.815-826
Published online, 23rd February, 2011
DOI: 10.3987/COM-11-12144
Facile Synthesis of Pyrano[3,2-e]indoles via the Base-Promoted Pictet-Spengler Reaction of Nb-Benzylserotonin

Koji Yamada, Sayaka Yamaguchi, Noriyuki Hatae, Takumi Abe, Tatsunori Iwamura, and Minoru Ishikura*

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan

Abstract

A novel and simple protocol for the synthesis of 1-(2-aminoethyl)pyrano[3,2-e]indole derivatives has been developed using the Pictet-Spengler reaction of Nb-benzylserotonin with α,β–unsaturated aldehydes in the presence of Et3N in 2-propanol or MeOH.