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Synthesis of Functionalized 1,2,3,4-Tetrahydro-β-carbolines from Enamino Ketones

✍ Scribed by Tietze, Lutz F. ;Wichmann, Jürgen

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
614 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Reaction of tryptamine (1) with 2 and 3 gives the enamino ketones 4a and 5, resp., which on treatment with trifluoroacetic acid lead to the 2‐substituted indoles 8 and 9, respectively. Acylation of 4a followed by reaction with trifluoroacetic acid or a Lewis acid affords the 1,2,3,4‐tetrahydro‐β‐carbolines 7b–e in excellent yields. Treatment of 8 with anhydrides like (CF~3~CO)~2~O also yields the 1,2,3,4‐tetrahydro‐β‐carboline 7f. The trichloromethylcarbonyl group in 7 can easily be converted into an ester moiety by reaction with an alcohol in the presence of K~2~CO~3~.

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