Electrophilic carbonyl activation: competing condensative cyclizations of tryptamine derivatives

A series of tryptamine derived bisindole substrates were subjected to electrophilic activation of the functional grouping at their α-nitrogen in the form of iminium ions to enable cyclization onto the sterically hindered indole substructure. Our observations regarding divergent cyclization outcomes...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 23; pp. 2995 - 3000
Main Authors Liu, Fan, Movassaghi, Mohammad
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.06.2015
Elsevier
Subjects
alkylation
chemical derivatives
chemical structure
Chemistry
Chemistry, Organic
Cyclization
Friedel–Crafts
Iminium ion
Indole
ions
Physical Sciences
Science & Technology
Tryptamine
Friedel–Crafts
Tryptamine
Cyclization
Iminium ion
Indole
ROOM-TEMPERATURE
PICTET-SPENGLER REACTION
NATURAL-PRODUCTS
DECARBOXYLATION
(-)-TRIGONOLIIMINES
BIOSYNTHESIS
BIOLOGICAL-ACTIVITY
Friedel-Crafts
CHEMISTRY
INDOLE ALKALOIDS
STEREOCHEMICAL ASSIGNMENT
tryptamine
iminium ion
indole
cyclization
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Summary:A series of tryptamine derived bisindole substrates were subjected to electrophilic activation of the functional grouping at their α-nitrogen in the form of iminium ions to enable cyclization onto the sterically hindered indole substructure. Our observations regarding divergent cyclization outcomes using electronically distinct bisindole substrates are described. Surprising preference for the Friedel–Crafts alkylation reaction and evidence for an intriguing reversible spirocyclization are discussed.
Bibliography:NIH RePORTER
ObjectType-Article-1
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content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.09.022