Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue 12, Pages 2103-2107Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202000554
Keywords
Tryptamines; Cyanide; Imino-Stetter reaction; Indoles; Nitrile
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Funding
- National Research Foundation of Korea (NRF) - Korean Government [NRF-2018R1D1A1A02086110, NRF-2014-011165]
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Herein, we describe the development of a two-step protocol for the synthesis of 2-substituted tryptamine derivatives from 2-aminocinnamyl nitriles and aldehydes. The cyanide-catalyzed imino-Stetter reaction of 2-aminocinnamyl nitriles and aldehydes provided 2-substituted indole-3-acetonitrile derivatives. Subsequent reduction of the nitrile group afforded the desired 2-substituted tryptamine derivatives. The utility of this protocol was demonstrated in the synthesis of a potential inhibitor of 15-lipoxygenase. Furthermore, the resulting 2-substituted indole-3-acetonitriles were converted to several 2,3-disubstituted indole derivatives upon transformation of the nitrile group into other functional groups.
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