Abstract
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.
Original language | English |
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Pages (from-to) | 2103-2107 |
Number of pages | 5 |
Journal | Asian Journal of Organic Chemistry |
Volume | 9 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2020 Dec |
Bibliographical note
Funding Information:This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF‐2018R1D1A1A02086110 and NRF‐2014‐011165, Center for New Directions in Organic Synthesis).
Publisher Copyright:
© 2020 Wiley-VCH GmbH
Keywords
- Cyanide
- Imino-Stetter reaction
- Indoles
- Nitrile
- Tryptamines
ASJC Scopus subject areas
- Organic Chemistry