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- Title
One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides.
- Authors
Rajasekar, Shanmugam; Yadagiri, Dongari; Anbarasan, Pazhamalai
- Abstract
A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-β-carboline and tryptoline.
- Subjects
INDOLE compounds; ETHYLATION; PYRROLES; ALKYNES; SULFONYL azides; CARBON-hydrogen bonds
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 47, p17079
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201502201