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Synthesis of 1,4-Enamino Ketones by [3,3]-Rearrangements of Dialkenylhydroxylamines

✍ Scribed by Pecak, Wiktoria H.; Son, Jongwoo; Burnstine, Amy J.; Anderson, Laura L.

Book ID
125495729
Publisher
American Chemical Society
Year
2014
Tongue
English
Weight
780 KB
Volume
16
Category
Article
ISSN
1523-7060

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## 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‐tet